Produced By The Action Of A Glycosyl Transferase (e.g., Alpha, Beta, Gamma-cyclodextrins By The Action Of Glycosyl Transferase On Starch, Etc.) Patents (Class 435/97)
  • Patent number: 5773256
    Abstract: Disclosed is a process of enzymatically preparing .alpha.-glucoside esters. First, .alpha.-glucosides are produced by placing an acyclic alcohol or a mixture of acyclic alcohols having a water solubility of at least 2.7% v/v at 20.degree. C. in contact with starch, maltodextrins or maltose, in the presence of a purified enzymatic preparation having .alpha.-transglucosylation activity, wherein the enzymatic preparation is free of .beta.-glucosidase activity. Then, the .alpha.-glucosides are contacted with at least one fatty acid and a preparation having lipase activity to produce the .alpha.-glucoside esters, which may then be recovered. The preparation having .alpha.-transglucosylation activity may originate from a fungus such as Talaromyces duponti, Aspergillus niger, Aspergillus oryzae or Aspergillus batatae.
    Type: Grant
    Filed: June 5, 1995
    Date of Patent: June 30, 1998
    Assignee: Ulice SA
    Inventors: Vincent P. Pelenc, Francois M.B. Paul, Pierre F. Monsan
  • Patent number: 5759823
    Abstract: Oligosaccharide compounds that are substrates and inhibitors of glycosyltransferase and glycosidase enzymes and compositions containing such compounds are disclosed. A method of glycosylation is also disclosed. An E. coli transformed with phagemid CMPSIL-1, which phagemid comprises a gene for a modified CMP-sialic acid synthetase enzyme, which transformed E. coli has the ATCC accession No. 68531 is also provided.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: June 2, 1998
    Assignee: Scripps Research Institute
    Inventors: Chi-Huey Wong, Yoshitaka Ichikawa, Gwo-Jenn Shen
  • Patent number: 5753469
    Abstract: A .beta.-fructofuranosidase with a molecular weight of 49,000.+-.5,000 daltons on SDS-PAGE, an isoelectric point of 4.6.+-.0.5, an optimum pH of about 5.5-6.0, and an optimum temperature of about 50.degree. C. in the presence of calcium ion. The enzyme acts on saccharides with a .beta.-fructofuranosidic linkage and other substances including other saccharides, sugar alcohols, and alcohols to produce fructosyl-transferred saccharides in a relatively high yield.
    Type: Grant
    Filed: December 11, 1996
    Date of Patent: May 19, 1998
    Assignee: Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo
    Inventors: Tetsuya Nakada, Hiroto Chaen, Toshiyuki Sugimoto
  • Patent number: 5750875
    Abstract: The present invention is directed to the modification of reserve polysaccharides in plants. Specifically, it has been found that host plants can be successfully transformed with a nucleic acid sequence capable of expressing a chimeric reserve polysaccharide modification enzyme gene sequence which will synthesize novel reserve polysaccharides in plants or convert the transformed plant's endogenous starch reserves to novel starch degradation products.
    Type: Grant
    Filed: June 6, 1995
    Date of Patent: May 12, 1998
    Inventors: David M. Stalker, Christine K. Shewmaker, Janette V. Oakes
  • Patent number: 5731173
    Abstract: Extracellular fructosyltransferase of Acetobacter diazotrophicus was isolated and purified and its enzymatic properties were established. Cloning, sequencing and genetic manipulation of the fructosyltransferase gene so as to produce high levels of the enzyme in recombinant prokaryotic and eukaryotic cells. Both natural and recombinant fructosyltransferase of Acetobacter diazotrophicus produce fructose-containing oligosaccharides and fructans. The enzyme yields in particular high levels of fructooligosaccharides from sucrose, such as kestose and kestotetraose which can be used as natural low-calorie sweeteners.
    Type: Grant
    Filed: March 10, 1997
    Date of Patent: March 24, 1998
    Assignee: Center For Genetic Engineering and Biotechnology
    Inventors: Juan Gabriel Arrieta Sosa, Lazaro Hernandez Garcia, Alberto Coego Gonzalez, Guillermo Selman-Housein Sosa
  • Patent number: 5728554
    Abstract: The present invention provides improved methods for the formation of glycosidic linkages. These methods are useful for the preparation of compounds of formula:NeuAc.alpha.(2.fwdarw.3)Gal.beta.(1.fwdarw.4)(Fuc.alpha. 1.fwdarw.3)GlcN(R').beta.(1.fwdarw.3)Gal.beta.
    Type: Grant
    Filed: April 11, 1995
    Date of Patent: March 17, 1998
    Assignee: Cytel Corporation
    Inventors: Robert J. Bayer, Shawn DeFrees, Murray Ratcliffe
  • Patent number: 5705367
    Abstract: The present invention is directed to nucleic acids encoding glycosyltransferases, the proteins encoded thereby, and to methods for synthesizing oligosaccharides using the glycosyltransferases of the invention. In particular, the present application is directed to identification a glycosyltransferase locus of Neisseria gonorrhoeae containing five open reading frames for five different glycosyltransferases. The functionally active glycosyltransferases of the invention are characterized by catalyzing reactions such as adding Gal .beta..fwdarw.4 to GlcNAc or Glc; adding GalNAc or GlcNAc .beta.1.fwdarw.3 to Gal; and adding Gal .alpha.1.fwdarw.4 to Gal. The glycosyltransferases of the invention are particularly suited to the synthesis of the oligosaccharides Gal.beta.1.fwdarw.4GlcNAc.beta.1.fwdarw.3Gal.beta.1.fwdarw.4Glc (a mimic of lacto-N-neotetraose), GalNAc.beta.1.fwdarw.3Gal.beta.1.fwdarw.4GlcNAc.beta.1.fwdarw.3Gal.beta.1. fwdarw.4Glc.beta.1.fwdarw.4 (a mimic ganglioside), and Gal.alpha.1.fwdarw.4Gal.beta.1.
    Type: Grant
    Filed: July 18, 1996
    Date of Patent: January 6, 1998
    Assignee: The Rockefeller University
    Inventor: Emil C. Gotschlich
  • Patent number: 5658778
    Abstract: The present invention provides a novel .beta.1.fwdarw.6 N-acetylglucosaminyltransferase, which forms core 2 oligosaccharide structures in O-glycans, and a novel acceptor molecule, leukosialin, CD43, for core 2 .beta.1.fwdarw.6 N-acetylglucosaminyltransferase activity. The amino acid sequences and nucleic acid sequences encoding these molecules, as well as active fragments thereof, also are disclosed. A method for isolating nucleic acid sequences encoding proteins having enzymatic activity is disclosed, using CHO cells that support replication of plasmid vectors having a polyoma virus origin of replication. A method to obtain a suitable cell line that expresses an acceptor molecule also is disclosed.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: August 19, 1997
    Assignee: La Jolla Cancer Research Foundation
    Inventors: Minoru Fukuda, Marti F. A. Bierhuizen
  • Patent number: 5656308
    Abstract: Disclosed is a novel non-reducing oligosaccharide with neotrehalose structure represented by the general formula as shown by: ##STR1## The oligosaccharide is obtainable by exposing an aqueous solution containing neotrehalose to a saccharide-transferring enzyme, and has a superior stability, reduced sweetness, appropriate viscosity, no susceptibility to crystallization and less fermentability. These features make it very useful in various compositions including foods, beverages, cosmetics and pharmaceuticals.
    Type: Grant
    Filed: June 6, 1995
    Date of Patent: August 12, 1997
    Assignee: Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo
    Inventors: Hajime Aga, Takashi Shibuya, Toshiyuki Sugimoto, Toshio Miyake
  • Patent number: 5652124
    Abstract: .alpha.-Glycosyl hesperidin, a novel hesperidin derivative wherein equimolar or more D-glucose residues are bound to hesperidin via the .alpha.-bond, is formed by a saccharide-transferring enzyme in a liquid containing hesperidin and .alpha.-glucosyl saccharide. The .alpha.-glycosyl hesperidin is easily recovered from the reaction mixture with a synthetic macroporous resin. .alpha.-Glycosyl hesperidin is superior in water-solubility, substantially tasteless and odorless, free of toxicity, and readily hydrolyzable in vivo into hesperidin and D-glucose to exhibit the physiological activity inherent to hesperidin. Thus, .alpha.-glycosyl hesperidin is favorably usable in vitamin P-enriching agents, foods, beverages, tobaccos, foods, pet foods, pharmaceuticals for susceptive diseases, cosmetics and plastics.
    Type: Grant
    Filed: July 12, 1995
    Date of Patent: July 29, 1997
    Assignee: Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo
    Inventors: Hiromi Hijiya, Toshio Miyake
  • Patent number: 5635378
    Abstract: There is disclosed a variant-type carbohydrate hydrolase that has been increased transglycosylation activity by substituting another amino acid residue for the tyrosine residue that is present in the active center of the hydrolase, which hydrolase is an amylase or an enzyme analogous to amylase; a gene or a DNA sequence of the carbohydrate hydrolase with mutation introduced into the base sequence that encodes the tyrosine residue; and a vector or a transformant which comprises the DNA sequence. There is also disclosed a method for producing a variety of oligosaccharides and the like by using the variant-type carbohydrate hydrolase.
    Type: Grant
    Filed: June 6, 1995
    Date of Patent: June 3, 1997
    Assignee: Director-General of Agency of Industrial Science and Technology
    Inventors: Ikuo Matsui, Kazuhiko Ishikawa, Sachio Miyairi, Koichi Honda
  • Patent number: 5622844
    Abstract: A method of producing a mannosyl-cyclodextrin having a mannosyl group bonded to the hydroxyl group of the glucosyl group of a cyclodextrin via an alpha-bond. The method includes treating a liquid containing a cyclodextrin and an alpha-mannosyl compound with an alpha-mannosyl transfer agent.
    Type: Grant
    Filed: June 1, 1995
    Date of Patent: April 22, 1997
    Assignees: Ensuiko Sugar Refining Co., Ltd., Sumio Kitahata
    Inventors: Sumio Kitahata, Koji Hara, Koki Fujita, Nobuhiro Kuwahara, Kyoko Koizumi
  • Patent number: 5623071
    Abstract: A cyclodextrin having a galactosyl group which is bonded to a 6-hydroxyl group of a glucosyl group of the cyclodextrin via an .alpha.-bond or a .beta.-bond; a cyclodextrin having a mannosyl group which is bonded to a 6-hydroxyl group of the cyclodextrin via an .alpha.-bond.
    Type: Grant
    Filed: June 1, 1995
    Date of Patent: April 22, 1997
    Assignees: Ensuiko Sugar Refining Co., Ltd., Sumio Kitahata
    Inventors: Sumio Kitahata, Koji Hara, Koki Fujita, Nobuhiro Kuwahara, Kyoko Koizumi
  • Patent number: 5620872
    Abstract: A cyclodextrin which when added to water produces a haze-free solution is made by the use of starch which contains at least about 90% amylopectin in a two-stage process wherein first a starch hydrolysate is formed by means of an alpha-amylase or an acid and a second subsequent step wherein the cyclodextrin is formed by means of a cyclodextrin-glycosyl-transferase.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: April 15, 1997
    Assignee: American Maize-Products Company
    Inventors: Wen Shieh, Allan Hedges
  • Patent number: 5618705
    Abstract: Anti-inflammatory compounds are useful, for example, in treating arthritis and heart attack patients. Novel oligosaccharides useful in the rapid synthesis of certain anti-inflammatory compounds are disclosed, as is a rapid method of synthesizing the oligosaccharides. Low pH can loosen the acceptor specificity of galactosyltransferase (lactose synthase: EC 2.4.1.22), allowing the rapid synthesis of novel oligosaccharides. The disaccharides cellobiose (.beta.1.fwdarw.4), laminaribiose (.beta.1.fwdarw.3), gentiobiose (.beta.1.fwdarw.6) and maltose (.alpha.1.fwdarw.4) acted as acceptors for lactose synthase under low pH conditions. From these four acceptors, the following four novel trisaccharides were synthesized: Gal.sub.p (.beta.1.fwdarw.4)Glc.sub.p (.beta.1.fwdarw.3)-Glc, Gal.sub.p (.beta.1.fwdarw.4)Glc.sub.p (.beta.1.fwdarw.4)-Glc, Gal.sub.p (.beta.1.fwdarw.4)Glc.sub.p (.beta.1.fwdarw.6)-Glc and Gal.sub.p (.beta.1.fwdarw.4)Glc.sub.p (.alpha.1.fwdarw.4) Glc.
    Type: Grant
    Filed: May 31, 1995
    Date of Patent: April 8, 1997
    Assignee: Board of Supervisors of Louisiana State University Mechanical College
    Inventors: Roger A. Laine, Eunsun Yoon
  • Patent number: 5610047
    Abstract: Disclosed are novel non-reducing saccharide-forming enzyme, and its preparation and uses. The enzyme is obtainable from the culture of microorganisms such as Rhizobium sp. M-11 (FERM BP 4130) and Arthrobacter sp. Q36 (FERM BP-4316), and capable of forming non-reducing saccharides having a trehalose structure when allowed to act on reducing partial starch hydrolysates. Glucoamylase and .alpha.-glucosidase readily yield trehalose when allowed to act on the non-reducing saccharides. These non-reducing saccharides and trehalose are extensively useful in food products, cosmetics and pharmaceuticals.
    Type: Grant
    Filed: March 29, 1995
    Date of Patent: March 11, 1997
    Assignee: Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo
    Inventors: Kazuhiko Maruta, Michio Kubota, Toshiyuki Sugimoto, Toshio Miyake
  • Patent number: 5583042
    Abstract: This invention relates to an apparatus containing specific binary combinations of glycosyltransferases, for the synthesis of specific saccharide compositions such as, for example, oligosaccharides, polysaccharides, glycolipids, and glycopeptides.
    Type: Grant
    Filed: March 22, 1994
    Date of Patent: December 10, 1996
    Assignee: NEOSE Pharmaceuticals, Inc.
    Inventor: Stephen Roth
  • Patent number: 5565435
    Abstract: A novel .alpha.-glycosyl quercetin, wherein at least equimolar D-glucose residues are attached to quercetin via the .alpha.-bond, has a satisfactory water-solubility, light tolerance and stability, and exerts the inherent activity of quercetin in vivo. The .alpha.-glycosyl quercetin is prepared by a process comprising subjecting a solution containing quercetin and an .alpha.-glucosyl saccharide to the action of a saccharide-transferring enzyme to form an .alpha.-glycosyl quercetin, and recoverying the resultant .alpha.-glycosyl quercetin. The .alpha.-glycosyl quercetin can be advantageously used in combination with other materials in food products, cosmetic compositions and pharmaceutical compositions as a highly-safe and natural vitamin P-enriched agent, yellow-color-imparting agent, antioxidant, deodorant, stabilizer, quality-improving agent, antiseptic, prophylactic agent, therapeutic agent and ultraviolet-absorbing agent.
    Type: Grant
    Filed: February 15, 1995
    Date of Patent: October 15, 1996
    Assignee: Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo
    Inventors: Masaru Yoneyama, Satoshi Iritani, Toshio Miyake
  • Patent number: 5565341
    Abstract: A process for producing trehalose from inexpensive saccharide raw materials via an enzymic method uses stable enzymes with high productivity. The process includes incubating a saccharide raw material and an inorganic phosphoric acid and/or a salt thereof in the presence of phosphorylase to produce .alpha.-glucose 1-phosphate, and contacting the produced .alpha.-glucose 1-phosphate with glucose in the presence of a trehalose phosphorylase to produce trehalose. The isolation and purification of trehalose is easier in comparison to conventional fermentation methods.
    Type: Grant
    Filed: August 2, 1994
    Date of Patent: October 15, 1996
    Assignee: Kureha Chemical Industry Co., Ltd.
    Inventors: Eisaku Takahashi, Toshihiko Wada, Yutaka Konai
  • Patent number: 5556775
    Abstract: The present invention; is a method of producing .beta.-cyclodextrin at a higher efficiency from a raw material other than starch, comprising making a malto-oligosaccharide with 2 to 10 glucoses co-exist with cyclodextrin glucanotransferase in a solution containing an organic solvent which can precipitate 50% or more of .beta.-cyclodextrin when an excessive amount of the solvent is added to the solution of the .beta.-cyclodextrin and effecting the reaction at a lower temperature than 40.degree. C.
    Type: Grant
    Filed: June 22, 1994
    Date of Patent: September 17, 1996
    Assignees: Akebono Brake Industry Co., Ltd., Akebono Research and Development Center, Ltd.
    Inventors: Isao Karube, Nobuyuki Yoshida
  • Patent number: 5545587
    Abstract: The sequence of cyclomaltodextrin glucanotransferase (CGTase) gene derived from a microorganism of genus Bacillus and the amino acid sequence of CGTase are determined. A recombinant DNA carrying the CGTase gene is introduced by in vitro genetic engineering technique into a host microorganism of species Bacillus subtilis or Escherichia coli. The recombinant microorganism carrying the recombinant DNA autonomically proliferates to secrete a large amount of CGTase.
    Type: Grant
    Filed: November 4, 1993
    Date of Patent: August 13, 1996
    Assignee: Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo
    Inventors: Toshiyuki Sugimoto, Michio Kubota, Shuzo Sakia
  • Patent number: 5541083
    Abstract: A method for genetically engineering cells to produce soluble and secretable Golgi processing enzymes instead of naturally occurring membrane-bound enzymes. Cells are genetically engineered to express glycosyltransferases which lack both a membrane anchor and a retention signal. The resulting altered enzyme becomes soluble and secretable by the cell without losing its catalytic activity. Secretion of the soluble glycosyltransferase by the cell provides for increased production and simplified recovery of glycosyltransferase.
    Type: Grant
    Filed: March 10, 1994
    Date of Patent: July 30, 1996
    Assignees: The Regents of the University of California, Amgen
    Inventors: James C. Paulson, Eryn Ujita-Lee, Karen J. Colley, Beverly Adler, Jeffrey K. Browne, Jasminder Weinstein
  • Patent number: 5523099
    Abstract: Disclosed is a novel non-reducing oligosaccharide with neotrehalose structure represented by the general formula as shown by: ##STR1## The oligosaccharide is obtainable by exposing an aqueous solution containing neotrehalose to a saccharide-transferring enzyme, and has a superior stability, reduced sweetness, appropriate viscosity, no susceptibility to crystallization and less fermentability. These features make it very useful in various compositions including foods, beverages, cosmetics and pharmaceuticals.
    Type: Grant
    Filed: December 9, 1994
    Date of Patent: June 4, 1996
    Assignee: Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo
    Inventors: Hajime Aga, Takashi Shibuya, Toshiyuki Sugimoto, Toshio Miyake
  • Patent number: 5523218
    Abstract: Disclosed are (1) a novel galactosyl-cyclodextrin having a galactosyl group as bonded to the hydroxyl group of the glucosyl group of a cyclodextrin via an .alpha.-bond and a method of producing said galactosyl-cyclodextrin; (2) a novel galactosyl-cyclodextrin having a galactosyl group as bonded to the hydroxyl group of the glucosyl group of a cyclodextrin via a .beta.-bond and a method of producing said galactosyl-cyclodextrin; and (3) a novel mannosyl-cyclodextrin having a mannosyl group as bonded to the hydroxyl group of the glucosyl group of a cyclodextrin via an .alpha.-bond and a method of producing said mannosyl-cyclodextrin. The new branched cyclodextrins are expected to be widely useful in various fields of drug industry, food industry and cosmetic industry.
    Type: Grant
    Filed: December 30, 1994
    Date of Patent: June 4, 1996
    Assignees: Ensuiko Sugar Refining Co., Ltd., Sumio Kitahata
    Inventors: Sumio Kitahata, Koji Hara, Koki Fujita, Nobuhiro Kuwahara, Kyoko Koizumi
  • Patent number: 5516665
    Abstract: A one-pot glycosylation reaction is disclosed in which a N-acetylgalactosamine (GalNAc) or N-acetylglucosamine (GlcNAc) group is enzymatically transferred to an acceptor molecule. The starting glycoside is a N-acetylamino monosaccharide 1-phosphate that is enzymatically converted to its UDP derivative via UTP and a pyrophorylase. The formed UDP derivative is epimerized, and the epimerized UDP derivative is used in the enzyme-catalyzed glycosyl transfer. That enzyme-catalyzed glycosyl transfer to an acceptor releases UDP that is enzymatically converted to UTP for further conversion of the N-acetylamino monosaccharide 1-phosphate into its UDP derivative.
    Type: Grant
    Filed: September 13, 1993
    Date of Patent: May 14, 1996
    Assignee: The Scripps Research Institute
    Inventor: Chi-Huey Wong
  • Patent number: 5510250
    Abstract: Disclosed is a novel non-reducing oligosaccharide with neotrehalose structure represented by the general formula as shown by: ##STR1## The oligosaccharide is obtainable by exposing an aqueous solution containing neotrehalose to a saccharide-transferring enzyme, and has a superior stability, reduced sweetness, appropriate viscosity, no susceptibility to crystallization and less fermentability. These features make it very useful in various compositions including foods, beverages, cosmetics and pharmaceuticals.
    Type: Grant
    Filed: March 14, 1995
    Date of Patent: April 23, 1996
    Assignee: Kabushiki Kaisha Hayashibara Seibutsu
    Inventors: Hajime Aga, Takashi Shibuya, Toshiyuki Sugimoto, Toshio Miyake
  • Patent number: 5501957
    Abstract: A method of assaying for glycosyltransferase activity in a sample. In a first step, a sample is reacted with a first sugar donor and an acceptor substrate to produce a transferase product. The first sugar donor and acceptor substrate are selected such that the sugar from the first sugar donor is capable of being transferred to the acceptor substrate in the presence of the glycosyltransferase to be assayed. In a second step, the transferase product is reacted with a second sugar donor having a sugar which is labelled with a labelling agent and an enzyme which is capable of transferring the sugar from the second sugar donor to the transferase product to produce a labelled transferase product and which has a higher affinity for the glycosyltransferase product compared to the affinity of the glycosyltransferase for the acceptor substrate. The labelling agent activity of the labelled transferase product or unreacted second sugar donor is assayed to determine transferase activity in the sample.
    Type: Grant
    Filed: August 22, 1994
    Date of Patent: March 26, 1996
    Assignee: Mount Sinai Hospital Corporation
    Inventors: James W. Dennis, Katherine A. Siminovitch, Alessandro Datti
  • Patent number: 5501968
    Abstract: Novel cyclodextrin glycosyl transferases (CGTase) can be produced by anaerobic cultivation of strains of Thermoanaerobacter or Thermoanaerobium. They are more thermostable than known CGTases and have temperature optimum about 95.degree. C.The novel CGTases can be used for starch liquefaction at pH 4.5 and temperature exceeding 100.degree. C. in the production of dextrose or ethanol. They can also be used for conversion of liquefied starch to cyclodextrin at a temperature of 80.degree.-90.degree. C.A method for enzymatically converting solid and liquefied starch into cyclodextrin using cyclodextrin glycosyl transferases (CGTase) elaborated by thermophilic obligate anaerobic strains belonging to the genus Clostridium. These CGTases are characterized by thermostability and a capability to liquefy starch and/or to convert liquefied starch to cyclodextrin at pH 5.0-5.5 and 60.degree.-90.degree. C.
    Type: Grant
    Filed: May 24, 1993
    Date of Patent: March 26, 1996
    Assignee: Novo Nordisk A/S
    Inventors: Robert L. Starnes, Philip C. Trackman, Dennis M. Katkocin
  • Patent number: 5492829
    Abstract: The particular strain of Klebsiella oxytoca No. 19-1 has been isolated from soil which produces a cyclomaltoglucanotransferase enzyme capable of converting starch to .alpha.-cyclodextrin in very high proportion, nearly close to 100 percent, rather than another types of cyclodextrins.
    Type: Grant
    Filed: March 23, 1993
    Date of Patent: February 20, 1996
    Assignee: Lotte Confectionery Co., Ltd.
    Inventors: Jang Youn Choi, Jae Ho Lee, Kee Hyuh Choi, Ik Boo Kwon
  • Patent number: 5474917
    Abstract: A cyclodextrin glycosyltransferase (CGTase) which, in the conversion of starch or starch-like substrates to CD, produces .gamma.-CD in an increased amount, and whose protein sequence, in the region between amino acid position 180 and amino acid position 240, contains the amino acid sequence (SEQ ID NO: 1), where position 1 of the protein sequence is the beginning of the signal peptide of the CGTase and Xxx denotes a natural amino acid.
    Type: Grant
    Filed: June 22, 1994
    Date of Patent: December 12, 1995
    Assignee: Consortium fur elektrochemische Industrie GmbH
    Inventors: Georg E. Schulz, Anton Candussio
  • Patent number: 5472859
    Abstract: The present invention discloses a method of synthesizing a novel form of cellulose I as well as methods of synthesizing a novel form of cellulose I in vitro. One method comprises contacting an activated saccharide substrate with an endoglucanase in an appropriate organic solvent/buffer ratio. The invention also encompasses a partially purified endoglucanase and a method of synthesizing cellooligosaccharides. A second method comprises contacting a nucleotide sugar with a purified glycosyl transferase in an appropriate buffer medium to insure polymerization and crystallization of parallel glucan chains from the enzyme/micelle complex to form cellulose I.
    Type: Grant
    Filed: August 2, 1993
    Date of Patent: December 5, 1995
    Inventors: R. Malcolm Brown, Jr., Shiro Kobayashi, Krystyna Kudlicka, Shigenori Kuga, Jong Lee, Likun Li, Kazuo Okuda, Shin-Ichiro Shoda
  • Patent number: 5468491
    Abstract: Method of producing oat extract from rolled oats and oat flour by performing a series of mixing, cooking, filtering and concentrating steps. The method comprises the steps of mixing rolled white oats with oat flour, bacterial or fungal enzymes, and water to form an oat/enzyme solution. The oat/enzyme solution is then mashed by cooking the solution to convert the starches present in the oats into sugars. The undissolved solids remaining from the rolled oats are separated from the oat mash by filtering the cooked oat mash using some of the undissolved solids as a filter bed. The filtering operation produces oat wort which is then concentrated to produce oat extract.
    Type: Grant
    Filed: January 11, 1994
    Date of Patent: November 21, 1995
    Inventor: Ronald G. Targan
  • Patent number: 5463039
    Abstract: A method of preparing a hetero-branched cyclodextrin comprising a glucosyl or a maltosyl group side chain and a mannosyl group .alpha.-bonded to a hydroxyl group of the glucosyl group or the maltosyl group of the side chain, the method involving reacting a liquid containing a branched cyclodextrin having a glucosyl or maltosyl group as the side chain and an .alpha.-mannosyl compound with an .alpha.-mannosyl transfer enzyme.
    Type: Grant
    Filed: June 21, 1994
    Date of Patent: October 31, 1995
    Assignees: Ensuiko Sugar Refining Co., Ltd., Osaka-shi, Kyoko Koizumi
    Inventors: Koji Hara, Koki Fujita, Nobuhiro Kuwahara, Sumio Kitahata, Kyoko Koizumi
  • Patent number: 5455168
    Abstract: Disclosed is a novel non-reducing saccharide-forming enzyme. The enzyme can be obtained from the culture of microorganisms such as Rhizobium sp. M-11 (FERM BP 4130) and Arthrobacter sp. Q36 (FERM BP-4316), and is capable of forming non-reducing saccharides having a trehalose structure when allowed to act on reducing partial starch hydrolysates having a degree of polymerization of 3 or greater. Glucoamylase and .alpha.-glucosidase readily yield trehalose when allowed to act on the non-reducing saccharides. These non-reducing saccharides and trehalose are useful in food products, cosmetics and pharmaceuticals.
    Type: Grant
    Filed: December 27, 1993
    Date of Patent: October 3, 1995
    Assignee: Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo
    Inventors: Kazuhiko Maruta, Michio Kubota, Toshiyuki Sugimoto, Toshio Miyake
  • Patent number: 5453369
    Abstract: The present invention relates to a novel cycloisomaltooligosaccharide selected from the group consisting of novel cycloisomaltoheptaose having a cyclic structure composed of 7 glucose residues in .alpha.-1,6 linkage, novel cycloisomaltooctaose having a cyclic structure composed of 8 glucose residues in .alpha.-1,6 linkage and novel cycloisomaltononaose having a cyclic structure composed of 9 glucose residues in .alpha.-1,6 linkage, novel cycloisomaltooligosaccharide synthase forming said oligosaccharides from dextran, and a process for producing said oligosaccharides by use of said enzyme or a microorganism capable of producing said enzyme.
    Type: Grant
    Filed: August 2, 1994
    Date of Patent: September 26, 1995
    Assignees: Kikkoman Corporation, Noda Institute for Scientific Research
    Inventors: Tetsuya Oguma, Tatsuo Horiuchi, Koichiro Tobe
  • Patent number: 5426178
    Abstract: Anti-inflammatory compounds are useful, for example, in treating arthritis and heart attack patients. Novel oligosaccharides useful in the rapid synthesis of certain anti-inflammatory compounds are disclosed, as is a rapid method of synthesizing the oligosaccharides. Low pH can loosen the acceptor specificity of galactosyltransferase (lactose synthase: EC 2.4.1.22 ), allowing the rapid synthesis of novel oligosaccharides. The disaccharides cellobiose (.beta.1.fwdarw.4) , laminaribiose (.beta.1.fwdarw.3) , gentiobiose (.beta.1.fwdarw.6) and maltose (.alpha.1.fwdarw.4) acted as acceptors for lactose synthase under low pH conditions. From these four acceptors, the following four novel trisaccharides were synthesized: Gal.sub.p (.beta.1.fwdarw.4)Glc.sub.p (.beta.1.fwdarw.3)-Glc, Gal.sub.p (.beta.1.fwdarw.4)Glc.sub.p (.beta.1.fwdarw.4)-Glc, Gal.sub.p (.beta.1.fwdarw.4)Glc.sub.p (.beta.1.fwdarw.6)-Glc and Gal.sub.p (.beta.1.fwdarw.4)Glc.sub.p (.alpha.1.fwdarw.4)Glc.
    Type: Grant
    Filed: March 31, 1993
    Date of Patent: June 20, 1995
    Assignee: Board of Supervisors of Louisiana State University and Agricultural and Mechanical College
    Inventors: Roger A. Laine, Eunsun Yoon
  • Patent number: 5422254
    Abstract: Two nucleotide sequences encoding two different polypeptides found in yeast trehalose synthase have been isolated and cloned. The coding sequences can be inserted into suitable vectors and used to transform host cells. The transformed cells will produce increased amounts of trehalose compared to the untransformed wild types and have increased tolerance to a variety of stresses, in particular to decreased availability of water. The invention may be used to improve the stress tolerance of organisms, to increase the storage life of foodstuffs and to produce trehalose economically on an industrial scale in an organism (e.g, baker's yeast) that is a traditional and safe foodstuff.
    Type: Grant
    Filed: February 28, 1992
    Date of Patent: June 6, 1995
    Assignee: Oy Alko Ab
    Inventors: John Londesborough, Outi Vuorio
  • Patent number: 5421733
    Abstract: A process for preparing difucosyl Y.sub.2 antigen (dimeric Le.sup.x) , said process comprising: (1) preparing a lactonorhexaosylceramide backbone or a lactonorhexaosylsaccharide backbone linked to a carrier molecule; and (2) enzymatically fucosylating said backbone at the III.sup.3 and V.sup.3 positions through an .alpha.1.fwdarw.3 linkage. A process for preparing Le.sup.y antigen analogues, said process comprising: (1) preparing a lactonorhexaosyl-ceramide backbone or a lactonorhexaosylsaccharide backbone linked to a carrier molecule; and (2) enzymatically fucosylating said backbone at the terminal .beta.-Gal through an .alpha.1.fwdarw.2 linkage; and (3) enzymatically fucosylating said backbone at one or more positions through an .alpha.1.fwdarw.3 linkage, provided that steps (2) and (3) can be conducted simultaneously or in any order.
    Type: Grant
    Filed: May 24, 1991
    Date of Patent: June 6, 1995
    Assignee: The Biomembrane Institute
    Inventors: Edward Nudelman, Khalid K. Sadozai, Henrik Clausen, Sen-itiroh Hakomori, Mark Stroud
  • Patent number: 5409817
    Abstract: A single vessel cyclic synthesis process for preparation of a sialyl.alpha.2.fwdarw.3.beta.galactoside is disclosed. In accordance with this process, a sialyltransferase acceptor is sialylated in an aqueous reaction medium by an .alpha.(2,3)sialyl transferase and CMP-sialic acid to form a sialyl donor substrate and CMP. In the presence of the trans-sialidase of Trypanosoma crusi, that sialyl donor substrate provides a sialyl group for a trans-sialidase acceptor, thereby preparing the sialyl.alpha.2.fwdarw.3.beta.galactoside. The .alpha.(2,3)sialyltransferase acceptor is reformed upon trans-sialidation of the latter acceptor, and the sialyl donor substrate is reformed using the .alpha.(2,3)sialyltransferase and a CMP-sialic acid recycling system that combines CMP with sialic acid that is also present in the vessel. The K.sub.m /V.sub.max value for the .alpha.(2,3)sialyltransferase acceptor is less than one-tenth the value of K.sub.m /V.sub.max of the trans-sialidase acceptor for the .alpha.
    Type: Grant
    Filed: May 4, 1993
    Date of Patent: April 25, 1995
    Assignee: Cytel, Inc.
    Inventors: Yukishige Ito, James C. Paulson
  • Patent number: 5407812
    Abstract: 2-O-.alpha.-D-Glucopyranosyl-L-ascrobic acid is crystallizable in its supersaturated solution. Crystalline 2-O-.alpha.-D-glucopyranosyl-L-ascorbic acid is substantially nonhygroscopic, free flowing, free of deliquescence, consolidation and direct reducing activity, but is readily soluble in water. Because of these, characteristics crystalline 2-O-.alpha.-D-glucopyranosyl-L-ascorbic acid is handleable with an ease, and superiorly high in stability and physiological activities. Thus, crystalline 2-O-.alpha.-D-glucopyranosyl-L-ascorbic acid is favorably useful in vitamin C-enriching agents, foodstuffs, pharmaceuticals and cosmetics.
    Type: Grant
    Filed: November 12, 1993
    Date of Patent: April 18, 1995
    Assignee: Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo
    Inventors: Shuzo Sakai, Masaru Yoneyama, Toshio Miyake
  • Patent number: 5376537
    Abstract: A process for the production of cyclodextrins, comprising reacting non-treated starch with cyclodextrin-glycosyl-transferase produced by Bacillus ohbensis (FERM BP-3180), or produced by a mutant derived from Bacillus ohbensis (e.g., FERM BP-3180), or produced by any other strain in which the CGTase gene from B. ohbensis has been cloned, in an aqueous solution at pH between 6.5 and 8.8 and extracting the cyclodextrins from the reaction mixture by ultrafiltration, is provided.
    Type: Grant
    Filed: October 18, 1991
    Date of Patent: December 27, 1994
    Assignees: Orsan, Mercian Corporation
    Inventors: Pierre H. Cami, Didier B. Majou
  • Patent number: 5374541
    Abstract: A single reaction vessel process for the synthesis of a sialylated galactoside is disclosed. The synthesis utilizes a .beta.-galactosidase to catalyze the reaction of a galactose-containing substrate and an acceptor to form a new galactosyl glycoside that is then sialylated using a cyclic multienzyme synthesis system to form CMP-sialic acid that sialylates the formed galactosyl glycoside in the presence of an .alpha.-sialyltransferase. The value of K.sub.m /V.sub.max for the formed galactosyl glycoside as a substrate for the .alpha.-sialyltransferase is less than one-third the K.sub.m /V.sub.max value for the galactose-containing substrate for that .alpha.-sialyltransferase.
    Type: Grant
    Filed: May 4, 1993
    Date of Patent: December 20, 1994
    Assignees: The Scripps Research Institute, Cytel Corporation
    Inventors: Chi-Huey Wong, Federico C. A. Gaeta
  • Patent number: 5364794
    Abstract: A simplified process is provided for producing saccharides of definite chain length, such as glucose, maltose and maltooligosaccharides, each in an isolated state and with a high purity.The process comprises transferring a saccharide chain, using a saccharide chain transferase, from a saccharide chain source to a substance substantially separable from the saccharides mentioned above and treating the thus-obtained oligosaccharide with an enzyme capable of excising the saccharide chain of definite chain length in an exo manner.
    Type: Grant
    Filed: February 4, 1993
    Date of Patent: November 15, 1994
    Assignee: Nippon Shinyaku Company Limited
    Inventors: Yohji Ezure, Shigeaki Maruo, Katsunori Miyazaki, Naoyoshi Yamada
  • Patent number: 5360733
    Abstract: The present invention provides a novel .beta.1.fwdarw.6 N-acetylglucosaminyltransferase, which forms core 2 oligosaccharide structures in O-glycans, and a novel acceptor molecule, leukosialin, CD43, for core 2 .beta.1.fwdarw.6 N-acetylglucosaminyltransferase activity. The amino acid sequences and nucleic acid sequences encoding these molecules, as well as active fragments thereof, also are disclosed. A method for isolating nucleic acid sequences encoding proteins having enzymatic activity is disclosed, using CHO cells that support replication of plasmid vectors having a polyoma virus origin of replication. A method to obtain a suitable cell line that expresses an acceptor molecule also is disclosed.
    Type: Grant
    Filed: October 1, 1992
    Date of Patent: November 1, 1994
    Assignee: La Jolla Cancer Research Foundation
    Inventors: Minoru Fukuda, Marti F. A. Bierhuizen
  • Patent number: 5336617
    Abstract: The present invention relates to a process for preparing trehalulose and isomaltulose wherein at least the trehalulose-forming enzyme system of a trehalulose-forming microorganism is contacted with a sucrose solution to convert it into trehalulose and isomaltulose in the weight ratio of at least 4:1.
    Type: Grant
    Filed: April 12, 1993
    Date of Patent: August 9, 1994
    Assignees: Mitsui Sugar Co., Ltd., Suedzucker AG Mannheim/Ochsenfurt
    Inventors: Toshiaki Sugitani, Kenichiro Tsuyuki, Yukie Miyata, Tadashi Ebashi, Hideaki Okui, Yoshikazu Nakajima, Kenzo Sawada
  • Patent number: 5326701
    Abstract: A process for producing alpha-cyclodextrin using cyclomaltoextrin glucanotransferase is disclosed. The enzyme is obtained from Bacillus macerans. Starch hydrolysate is treated with the enzyme at a temperature of between about 15.degree. C. and about 40.degree. C. wherein the conversion is performed in the presence of cyclohexane and substantially no gamma-cyclodextrin is produced. The resulting alpha-cyclodextrin is then recovered.
    Type: Grant
    Filed: March 9, 1993
    Date of Patent: July 5, 1994
    Assignee: American Maize Technology Inc.
    Inventors: Wen J. Shieh, Allan R. Hedges
  • Patent number: 5322693
    Abstract: Lactoneotrehalose, a novel saccharide shown by the formula O-.beta.-D-galactopyranosyl-(1.fwdarw.4)-O-.beta.-D-glucopyranosyl .alpha.-D-glucopyranoside, is prepared by allowing a saccharide-transferring enzyme to act on an aqueous solution containing lactose and amylaceous substance. Lactoneotrehalose is a non-reducing oligosaccharide, extremely stable, readily soluble in water, and substantially free of hygroscopicity, as well as having a satisfiable quality and moderate sweetness. These render lactoneotrehalose very useful in the preparations of orally-administrable products, cosmetics and pharmaceuticals.
    Type: Grant
    Filed: April 5, 1993
    Date of Patent: June 21, 1994
    Assignee: Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo
    Inventors: Takashi Shibuya, Hiroto Chaen, Shuzo Sakai
  • Patent number: 5320954
    Abstract: An aromatic substituted glycoside is disclosed of the formula ##STR1## wherein the configuration of the substituted --OR on the anomeric carbon is alpha, n is an integer of 0 or 1, and R is a substituted aromatic radical selected from the group ##STR2## where R.sub.1 through R.sub.6 are independently halogen, NO.sub.2, SO.sub.3 H, COR.sub.7, ##STR3## where R.sub.7 is lower alkyl; and includes its stereoisomers, optical isomers and geometric isomers and mixtures of the foregoing isomers. These substrates are useful as direct substrates for alpha-amylases. A process for the preparation of the substrates and related substances is also described.
    Type: Grant
    Filed: September 3, 1992
    Date of Patent: June 14, 1994
    Assignee: Hoechst Celanese Corporation
    Inventors: Rodrigo G. Chavez, Harold David, Ernest K. Metzner, Gerald F. Sigler, Emily S. Winn-Deen
  • Patent number: 5314810
    Abstract: A fructose transferring enzyme is immobilized by adsorption on a granular carrier having a primary to quaternary amine. The carrier is preferably an epoxy polymer, a vinyl polymer or a chitosan derivative having a primary, secondary or tertiary amine. Immobilization can be performed without or with a crosslinking agent. The immobilized enzyme is used for producing fructooligosaccharides by passing a sucrose solution through a column containing the immobilized enzyme.
    Type: Grant
    Filed: May 19, 1992
    Date of Patent: May 24, 1994
    Assignee: Meiji Seika Kaisha, Ltd.
    Inventors: Toshiaki Kono, Goichi Yamaguchi, Hidemasa Hidaka
  • Patent number: 5294458
    Abstract: The pet food of the present invention contains lactosucrose which is substantially uniformly mixed in a meal in a range of 0.025 to 3.0% by weight on a dry basis. Lactosucrose keeps intestines of the pets in order, and provides a good taste and a great effect on deodorizing feces and urine discharged by the pets.
    Type: Grant
    Filed: August 27, 1992
    Date of Patent: March 15, 1994
    Assignees: Maruha Corporation, Ensuiko Sugar Refining Co., Ltd.
    Inventor: Isao Fujimori