Peptide Sweetners Patents (Class 530/801)
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Patent number: 8524251Abstract: The invention provides proteins from Neisseria meningitidis, including the amino acid sequences and the corresponding nucleotide sequences. The proteins are predicted to be useful antigens for vaccines and/or diagnostics.Type: GrantFiled: January 26, 2012Date of Patent: September 3, 2013Assignees: J. Craig Venter Institute, Inc., Novartis AGInventors: Claire Fraser, Cesira Galeotti, Guido Grandi, Erin Hickey, Vega Masignani, Marirosa Mora, Jeremy Petersen, Mariagrazia Pizza, Rino Rappuoli, Giulio Ratti, Vincenzo Scarlato, Maria Scarselli, Herve Tettelin, J. Craig Venter
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Publication number: 20010006694Abstract: The invention relates to dry foodstuffs with <10% by wt moisture, containing dipeptide sweetener and optionally a component that is reactive with it, both in a sugar-free and in a sugar-containing form. The invention relates especially to products which also contain flavourings based on aldehydes. With the invention dry foodstuffs are produced with improved sweetness stability and storage stability and improved flavour when the dipeptide sweetener is a sweetening salt of an aspartic-acid-derived dipeptide sweetener and a derivative of a sweetening acid. The particle size of the sweetening salt is preferably smaller than 200 &mgr;m. The invention also relates to processes for production of such dry foodstuffs using the dipeptide sweetener substantially in solid, dry form.Type: ApplicationFiled: January 19, 1999Publication date: July 5, 2001Inventors: JOHN FRY, ANNETTE HOEK, LEOPOLD F. W. VLEUGELS
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Patent number: 5837483Abstract: An enzymatic method for producing N-formyl-.alpha.-L-aspartyl-L-phenylalanine methyl ester by a condensation reaction between N-formyl-L-aspartic acid and L-phenylalanine methyl ester or D,L-phenylalanine methyl ester, which comprises: supplying an organic phase comprising a water-immiscible solvent containing N-formyl-L-aspartic acid and L- or D,L-phenylalanine methyl ester onto an aqueous phase comprising a thermolysin-like metalloprotease; proceeding the condensation reaction in the aqueous phase to produce N-formyl-.alpha.-L-aspartyl-L-phenylalanine methyl ester; and extracting the N-formyl-.alpha.-L-aspartyl-L-phenylalanine methyl ester thus produced from the aqueous phase to the organic phase.Type: GrantFiled: September 29, 1997Date of Patent: November 17, 1998Assignee: Holland Sweetener Company V.o.F.Inventor: Akira Hirata
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Patent number: 5763392Abstract: Method for lowering the plasma glucose levels of diabetics by administering myo-inositol. Also the invention concerns a nutritional composition containing myo-inositol.Type: GrantFiled: May 15, 1996Date of Patent: June 9, 1998Inventors: Barbara C. Hansen, Harry L. Greene, Heidi K. Ortmeyer
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Patent number: 5741537Abstract: Disclosed herein is a protein sweetener that has been isolated from Pentadiplandra brazzeana Baillon. The sweetener is thermostable, lysine rich, and has a relative long lasting taste. Also disclosed is a recombinant host capable of producing the sweetener in large quantities. Compositions of this sweetener with other sweeteners are also disclosed.Type: GrantFiled: October 19, 1995Date of Patent: April 21, 1998Assignee: Wisconsin Alumni Research FoundationInventors: Bengt Goran Hellekant, Ding Ming
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Patent number: 5723165Abstract: Aspartyldipeptide compounds of the formula (I)L-Asp-X-NH-C*R.sub.1 R.sub.2 (I)where R.sub.1 is alkyl or alkoxymethyl, R.sub.2 is phenyl, benzyl, cyclohexyl or cyclohexylmethyl, C* has an (S) configuration when R.sub.1 is alkyl and an (R) configuration when R.sub.1 is alkoxymethyl and X is a residue of a D-.alpha.-amino acid, a DL-.alpha.-amino acid or a residue of a cyclic or acyclic .alpha.,.alpha.-diallylamino acid and the bond between L-Asp and X is an .alpha.-bond; and their use as active ingredients in sweetener compositions.Type: GrantFiled: July 10, 1995Date of Patent: March 3, 1998Assignee: Ajinomoto Co., Inc.Inventors: Tadashi Takemoto, Yusuke Amino, Ryoichiro Nakamura
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Patent number: 5501712Abstract: The problems in crystallization of .alpha.-L-aspartyl-L-phenylalanine methyl ester, namely, problems in crystal slurry properties in solid-liquid separation, scaling at heat transfer surfaces, and the like, are solved by a method for crystallization of .alpha.-L-aspartyl-L-phenylalanine methyl ester which comprises cooling a solution of .alpha.-L-aspartyl-L-phenylalanine methyl ester by indirect heat exchange with a coolant while stirring, wherein the solution is cooled by circulating a coolant while continuously adding an aqueous solution of .alpha.-L-aspartyl-L-phenylalanine methyl ester dropwise to a crystallizing solution of .alpha.-L-aspartyl-L-phenylalanine methyl ester having a temperature difference of not greater than 20.degree. C. from the coolant, thereby to keep a temperature difference of not greater than 20.degree. C. between the coolant and the crystallizing solution.Type: GrantFiled: October 21, 1994Date of Patent: March 26, 1996Assignee: Ajinomoto Co., Inc.Inventors: Sou Abe, Shinichi Kishimoto
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Patent number: 5432262Abstract: Mixture containing .alpha.-L-aspartyl-L-phenylalanine methyl ester and 3-benzyl-6-carboxymethyl-2,5-dioxopiperazine are brought into contact with hydrochloric acid in an aqueous solvent to precipitate .alpha.-L-aspartyl-L-phenylalanine methyl ester hydrochloride and 3-benzyl-6-carboxymethyl-2,5-dioxopiperazine, which are then separated from each other by classification.Type: GrantFiled: January 12, 1993Date of Patent: July 11, 1995Assignee: Ajinomoto Co., Inc.Inventors: Tadashi Takemoto, Katsumi Sugiyama
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Patent number: 5425787Abstract: The problems in crystallization of .alpha.-L-aspartyl-L-phenylalanine methyl ester, namely, problems in crystal slurry properties in solid-liquid separation, scaling at heat transfer surfaces, and the like, are solved by a method for crystallization of .alpha.-L-aspartyl-L-phenylalanine methyl ester which comprises cooling a solution of .alpha.-L-aspartyl-L-phenylalanine methyl ester by indirect heat exchange with a coolant while stirring, wherein the solution is cooled by circulating a coolant while continuously adding an aqueous solution of .alpha.-L-aspartyl-L-phenylalanine methyl ester dropwise to a crystallizing solution of .alpha.-L-aspartyl-L-phenylalanine methyl ester having a temperature difference of not greater than 20.degree. C. from the coolant, thereby to keep a temperature difference of not greater than 20.degree. C. between the coolant and the crystallizing solution.Type: GrantFiled: February 28, 1994Date of Patent: June 20, 1995Assignee: Ajinomoto Co., Inc.Inventors: Sou Abe, Shinichi Kishimoto
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Patent number: 5350681Abstract: The present invention discloses a method for the enzymatic synthesis of a peptide. A protected peptide having a C-terminal carboxylate group or a protected, N-acyl amino acid having an alpha carboxylate group is reacted with a protected peptide having an N-terminal ammonium group or a protected amino acid having an alpha ammonium group in the presence of a condensation enzyme under conditions in which the carboxylate group and the ammonium group condense to form a protected, uncharged, peptide product. This peptide product is transported across a water-immiscible hydrophobic phase into an aqueous product phase and prevented from back diffusing across the water-immiscible hydrophobic phase. The peptide product can be converted, chemically or enzymatically, to a charged species that cannot back diffuse across the water-immiscible phase into the aqueous reaction phase.Type: GrantFiled: August 12, 1992Date of Patent: September 27, 1994Assignee: The Coca-Cola CompanyInventors: Guillermo A. Iacobucci, Daniel J. Brose, Roderick J. Ray, Paul van Eikeren
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Patent number: 5017690Abstract: N-formyl amino acid or peptide is deformylated by reaction with aniline or methylene dianiline over noble metal catalyst, e.g., Pt-on-carbon. N-formanilide is formed as by-product. The process is particularly useful in deformylating N-formyl aspartame.Type: GrantFiled: August 11, 1989Date of Patent: May 21, 1991Assignee: W. R. Grace & Co.-Conn.Inventor: Jennifer M. Quirk
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Patent number: 4851563Abstract: A method for the removal of the formyl group from an ester of an N-formyl peptide or N-formyl aminoacid, in which the ester is reacted with urea in the presence of a polar solvent and a strong acid.Type: GrantFiled: September 9, 1986Date of Patent: July 25, 1989Assignee: Lark S.p.A.Inventors: Goffredo A. Bolis, Giuseppe Cantarini, Marco Da Col
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Patent number: 4803300Abstract: Disclosed herein is a process for separating N-protected-.alpha.-L-aspartyl-L-phenylalanine, more particularly a process for selectively separating N-protected-.alpha.-L-aspartyl-L-phenylalanine from a solution of N-protected-.alpha.-L-aspartyl-L-phenylalanine containing at least N-protected-.alpha.-L-aspartyl-D-phenylalanine as impurity.Type: GrantFiled: August 11, 1987Date of Patent: February 7, 1989Assignee: Ajinomoto Co., Inc.Inventors: Toyoto Hijiya, Tadashi Takemoto, Toshihide Yukawa
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Patent number: 4789758Abstract: A process is described for the synthesis of N-protected-L-.alpha.-aspartyl-L-phenylalanine by both (a) the rection of an N-protected-L-aspartic anhydride and a R.sub.1 -L-phenylalanine, and (b) the reaction of an N-protected-L-aspartic anhydride and L-phenylalanine in an aqueous medium in the presence of R.sub.2, where R.sub.1 may be an alkali metal salt, alkaline earth metal salt, ammonium salt or organic amine salt, and R.sub.2 may be an ammonium salt or an alkali or alkaline earth metal salt of an inorganic or organic acid.Type: GrantFiled: October 13, 1987Date of Patent: December 6, 1988Assignee: Ajinomoto Co., Inc.Inventors: Tadashi Takemoto, Toshihide Yukawa, Kunio Hisamitsu
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Patent number: 4780561Abstract: Disclosed herein is a process for preparing .alpha.-L-aspartyl-L-phenylalanine methyl ester or its hydrochloride from 5-benzyl-3,6-dioxo-2-piperazine acetic acid or its methyl ester, prepared without using L-penylalanine methyl ester which involves problems in its stability, as a raw material. Specifically, the process comprises: bringing 5-benzyl-3,6-dioxo-2-piperazine acetic acid in the presence of methanol or 5-benzyl-3,6-dioxo-2-piperazine acetic acid methyl ester in the presence or absence of methanol into contact with hydrochloric acid; isolating the thereby deposited .alpha.-L-aspartyl-L-phenylalanine methyl ester hydrochloride; and neutralizing said hydrochloride with an alkali as required. Preparation processes of 5-benzyl-3,6-dioxo-2-piperazine acetic acid or its methyl ester are also disclosed.Type: GrantFiled: December 9, 1987Date of Patent: October 25, 1988Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Ryuichi Mita, Takeshi Oura, Toshio Katoh, Chojiro Higuchi, Akihiro Yamaguchi
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Patent number: 4780528Abstract: Tripeptide sweeteners represented by formula (I)X--Asp--Y--ORwhereinX is glycine or a D or DL-isomer of alanine, .alpha.-aminobutyric acid, serine, threonine, norvaline, asparagine, B-methyl aspartate, proline or pipecolic acid, andY is a D, L or DL-isomer of alanine, phenylalanine, phenylglycine, serine or .beta.-aminobutyric acid or a salt thereof, andR is methyl, ethyl, propyl or isopropyl, are disclosed.Type: GrantFiled: November 4, 1985Date of Patent: October 25, 1988Assignee: Ajinomoto Co., Inc.Inventors: Tadashi Takemoto, Toyoto Hijiya, Toshihide Yukawa
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Patent number: 4778916Abstract: The present invention relates to a process for preparing .alpha.-L-aspartyl-L-phenylalanine methyl ester or its hydrochloride. .alpha.-L-aspartyl-L-phenylalanine methyl ester or its hydrochloride is prepared by a process comprising: condensating N-formyl-L-aspartic acid anhydride and L-phenylalanine in water or in water containing methanol at a pH in the range of 7-12 to form N-formyl-.alpha.-L-aspartyl-L-phenylalanine; acidifying the reaction mixture successively with hydrochloric acid in the presence of methanol without isolating the N-formyl-.alpha.-L-aspartyl-L-phenylalanine so as to bring it into contact with hydrochloric acid in the presence of methanol for reaction and thereby to deposit .alpha.-L-aspartyl-L-phenylalanine methyl ester hydrochloride; separating the .alpha.-L-aspartyl-L-phenylalanine methyl ester hydrochloride; and neutralizing said hydrochloride as required.Type: GrantFiled: November 17, 1987Date of Patent: October 18, 1988Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Ryuichi Mita, Toshio Katoh, Chojiro Higuchi, Takeshi Oura, Akihiro Yamaguchi
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Patent number: 4740616Abstract: A process is described for the synthesis of N-protected-L-.alpha.-aspartyl-L-phenylalanine by both (a) the reaction of an N-protected-L-aspartic anhydride and a R.sub.1 -L-phenylalanine, and (b) the reaction of an N-protected-L-aspartic anhydride and L-phenylalanine in an aqueous medium in the presence of R.sub.2, where R.sub.1 may be an alkali metal salt, alkaline earth metal salt, ammonium salt or organic amine salt, and R.sub.2 may be an ammonium salt or an alkali or alkaline earth metal salt of an inorganic or organic acid.Type: GrantFiled: July 1, 1986Date of Patent: April 26, 1988Assignee: Ajinomoto Co., Inc.Inventors: Tadashi Takemoto, Toshihide Yukawa, Kunio Hisamitsu
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Patent number: 4692512Abstract: alpha-L-Aspartyl-D-phenylglycine esters and amides are disclosed to be useful as high intensity sweeteners. These compounds can be used to sweeten a variety of foods, beverages and other oral products.Type: GrantFiled: December 20, 1985Date of Patent: September 8, 1987Assignee: The Procter & Gamble CompanyInventor: John M. Janusz
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Patent number: 4692513Abstract: Alpha-L-Aspartyl-D-heteroaromatic-substituted glycine esters and amides are disclosed to be useful as high intensity sweeteners. These compounds can be used to sweeten a variety of foods, beverages and other oral products.Type: GrantFiled: December 20, 1985Date of Patent: September 8, 1987Assignee: The Procter & Gamble CompanyInventors: Robert B. Blum, John M. Gardlik, John M. Janusz, George P. Rizzi
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Patent number: 4677220Abstract: A regioselective process for the preparation of .alpha.-L-aspartyl-L-phenylalanine methyl ester is disclosed. A controlled aqueous coupling reaction between .beta.-methyl-L-aspartate-N-carboxyanhydride and L-phenylalanine produces the aspartyl methyl ester of .alpha.-L-aspartyl-L-phenylalanine which is subsequently hydrolyzed and selectively esterified without isolation. The hydrochloride salt of .alpha.-L-aspartyl-L-phenylalanine methyl ester, which is selectively precipitated from the esterification mixture, can be neutralized to .alpha.-L-aspartyl-L-phenylalanine methyl ester.Type: GrantFiled: October 31, 1985Date of Patent: June 30, 1987Assignee: Monsanto CompanyInventors: Jacob S. Tou, Billy D. Vineyard
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Patent number: 4642367Abstract: A new process for preparing alfa-L-aspartyl-L-phenylalanine alkyl esters of formula I ##STR1## wherein R represents an alkyl group having from 1 to 5 carbon atoms, starting from the corresponding alfa-haloacyl-alfa-L-aspartyl-L-phenylalanine alkyl esters.Type: GrantFiled: July 15, 1985Date of Patent: February 10, 1987Assignee: Farchemia S.p.A.Inventor: Martino Finotto
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Patent number: 4638081Abstract: A process for preparing .alpha.-L-aspartyl-L-phenylalanine methyl ester consisting of:bringing N-formyl-L-aspartic anhydride and L-phenylalanine methyl ester, in a molar ratio equal or approximately equal to 1:1, into contact with a solid cation exchange resin having free sulphonic, phosphonic or carboxylic acid groups, the ration of the acid equivalents of said resin acid groups to the number of moles of the one or other reagent being equal to or less than about 1:1, and operating in the liquid phase in an inert organic solvent at a temperature of about 40.degree. C. or less, until a mixture of N-formyl-.alpha.-L-aspartyl-L-phenylalanine methyl ester and N-formyl-.beta.-L-aspartyl-L-phenylalanine methyl ester forms in which the .alpha. isomer prevails over the .beta. isomer;deformylating said N-formyl-.alpha.-L-aspartyl-L-phenylalanine methyl ester and N-formyl-.beta.-L-aspartyl-L-phenylalanine methyl ester; andseparating and recovering the .alpha.Type: GrantFiled: May 10, 1984Date of Patent: January 20, 1987Assignee: DE-BI Derivati Biologici International SpAInventor: Biagio Elefante
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Patent number: 4634792Abstract: This invention relates to novel sweeteners of the formula: ##STR1## wherein A is CO.sub.2 R wherein R is alkyl containing 1-3 carbon atoms;A' is hydrogen or alkyl containing 1-3 carbon atoms;Y is alkyl containing 4-11 carbon atoms, andM=0 or 1;and food-acceptable salts thereof.Type: GrantFiled: May 6, 1985Date of Patent: January 6, 1987Assignee: General Foods CorporationInventors: Paul R. Zanno, Ronald E. Barnett, Glenn M. Roy
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Patent number: 4622417Abstract: Dipeptides of certain .alpha.-amino dicarboxylic acids and etherified hydroxy .alpha.-amino-mono-carboxylic acid esters possess a high order of sweetness. These dipeptides have the following formula: ##STR1## wherein R is alkyl containing 1-3 carbon atoms;R.sub.1 is cycloalkyl, cycloalkenyl, lower alkyl substituted cycloalkyl or cycloalkenyl, bicycloalkyl, bicycloalkenyl or tricycloalkyl containing up to 10 ring carbon atoms and up to a total of 12 carbon atoms;R.sub.2 and R.sub.4 are each H or alkyl containing 1-3 carbon atoms;R.sub.3 is H, alkyl containing 1-6 carbon atoms or cycloalkyl containing 3-5 ring carbons;n=0, 1 or 2; andm=0 or 1;and food acceptable salts thereof.Type: GrantFiled: December 27, 1984Date of Patent: November 11, 1986Assignee: General Foods CorporationInventors: Ronald E. Barnett, Paul R. Zanno, Glenn M. Roy
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Patent number: 4622418Abstract: Amides of .alpha.-aminodicarboxylic acids and .beta.-aminoethers are low calorie sweetners.Type: GrantFiled: April 4, 1985Date of Patent: November 11, 1986Assignee: General Foods CorporationInventors: Ronald E. Barnett, Paul R. Zanno, Glenn M. Roy