Abstract: A chemoenzymatic method is disclosed for preparing N-[N-(3,3-dimethylbutyl)-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester via the enzymatic regioselective hydrolysis of neotame esters using lipases or esterases.
Abstract: 3,3-Dimethylbutanal is prepared from 3,3-dimethylbutanol. Intermediate 3,3-dimethylbutanol is obtained by reacting ethylene, isopropylene and sulfuric acid to produce a 3,3-dimethylbutyl ester which is hydrolyzed to the alcohol. The hvdrolysis step is effectively carried out by reactive distillation. Alternatively, 3,3-dimethylbutanal is prepared from 3,3-dimethylbutanol obtained by reduction of the corresponding carboxylic acid or 1,2-epoxy-3,3-dimethylbutane, or by hydrolysis of 1-halo-3,3-dimethylbutane. Fixed bed gas phase and stirred tank liquid phase processes are provided for converting 3,3-dimethylbutanol to 3,3-dimethylbutanal by catalytic dehydrogenation.
Type:
Grant
Filed:
May 19, 2000
Date of Patent:
June 3, 2003
Assignee:
The Nutrasweet Company
Inventors:
Jerry R. Ebner, Zhi Guo, Arnold Hershman, Loraine M. Klein, William D. McGhee, Mark D. Paster, Indra Prakash
Abstract: The present invention relates to a process for coating N-[N-(3,3-dimethylbutyl)-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester onto a carrier. The invention also relates to N-[N-(3,3-dimethylbutyl)-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester coated carrier compositions.
Abstract: The synthesis of N-[N-(3,3-dimethylbutyl)-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester via conversion under reducing conditions of novel imidazolidinone(s) is disclosed.
Type:
Grant
Filed:
November 17, 1999
Date of Patent:
October 15, 2002
Assignee:
The NutraSweet Company
Inventors:
Vladislav Orlovski, Indra Prakash, Mike G. Scaros, Christine M. V. Moore
Abstract: N-[N-(3,3-dimethylbutyl)-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester is crystallized in order to give highly pure product in high yield. In a preferred embodiment of the present invention, N-[N-(3,3-dimethylbutyl)-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester is crystallized directly from an aqueous methanol reaction mixture.
Type:
Grant
Filed:
November 24, 1999
Date of Patent:
July 23, 2002
Assignee:
The NutraSweet Company
Inventors:
Indra Prakash, Christine M. V. Moore, Kurt Wachholder
Abstract: This invention relates to the use of at least one taste modifying ingredient to modify at least one taste characteristic imparted by N-[N-(3,3-dimethylbutyl)-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester, or neotame, compositions containing the same, and use of modified forms of neotame that possess an improved taste, wherein at least one taste characteristic imparted by neotame is positively affect by the modification of neotame.
Type:
Grant
Filed:
May 10, 2000
Date of Patent:
April 9, 2002
Assignee:
The NutraSweet Company
Inventors:
Paula A. Gerlat, Gale C. Walters, Ihab E. Bishay, Indra Prakash, Tammy C. Jarrett, Nitin Desai, Harold A. Sawyer, Claire-Lise T. Bechert
Abstract: N-[N-(3,3-dimethylbutyl)-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester is converted from a light powder to relatively dustless, free-flowing particles with and without the use of binders using extrusion and spheronization processes. These particles are suitable for use in a variety of applications. Food products sweetened with extruded or spheronized N-[N-(3,3-dimethylbutyl)-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester and methods of sweetening food products with such N-[N-(3,3-dimethylbutyl)-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester are also disclosed.
Type:
Grant
Filed:
March 24, 2000
Date of Patent:
April 2, 2002
Assignee:
The NutraSweet Company
Inventors:
Aditi Dron, Ihab E. Bishay, Jim Fotos, Michael J. Trione
Abstract: The present invention provides materials and methods for production of D-phenylalanine by recombinant expression in a microorganisms of a D-aminotransferase gene and optionally a dadX gene in optional combination with eliminating or reducing expression of L-transaminase genes.
Type:
Grant
Filed:
April 19, 1995
Date of Patent:
March 19, 2002
Assignee:
The Nutrasweet Company
Inventors:
Ian Fotheringham, Paul P. Taylor, Roberta K. Yoshida
Abstract: Dipeptide sweeteners are disclosed that are basic salts of N-[N-(3,3-dimethylbutyl)-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester represented by the formula
wherein Xm+ is selected from the group consisting of Na+, K+, Al3+, Fe2+, Fe3+, Ca2+, Mg2+, NH4+ and Zn2+; Qs− absent or a physiologically acceptable counter anion; and m−s=n. Also disclosed is a liquid low-calorie sweetener containing such basic salts.
Abstract: This invention relates to the purification of N-[N-(3,3-dimethylbutyl)-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester by resolving a mixture of the alpha- and beta-isomers of N-[N-(3,3-dimethylbutyl)-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester using metal ions.
Type:
Grant
Filed:
August 21, 2000
Date of Patent:
May 1, 2001
Assignee:
The Nutrasweet Company
Inventors:
Indra Prakash, Joseph P. Haar, Jr., Robert Y. Zhao
Abstract: This disclosure relates to the co-crystallization of N-[N-(3,3-dimethylbutyl)-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester with sugar in various ratios. The sugar co-crystallized sweetener is very soluble in water and has no dusting problems.
Type:
Grant
Filed:
September 17, 1998
Date of Patent:
April 10, 2001
Assignee:
The NutraSweet Company
Inventors:
Jim Fotos, Ihab E. Bishay, Indra Prakash, Kurt Wachholder, Nitin Desai
Abstract: A process for preparing an agglomerate of N-[N-(3,3-dimethylbutyl)-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester and a carrier including the steps of: (a) providing a premix solution comprising N-[N-(3,3-dimethylbutyl)-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester and a binding agent; (b) fluidizing a carrier; and (c) applying the premix solution of step (a) onto said fluidized carrier to form an agglomerate of said N-[N-(3,3-dimethylbutyl)-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester and said carrier. Also the novel agglomerates prepared by the process of this invention.
Abstract: Dipeptide sweeteners are disclosed that are salts of N-[N-(3,3-dimethylbutyl)-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester represented by the formula
wherein X− is selected from the group consisting of Cl−, HSO4−, H2PO3−, citrate, HCO3−, furmarate, malate, maleiate, tartarate, acetate, benzoate or gluconate. Also disclosed is a liquid low-calorie sweetener containing such salts.
Abstract: Dipeptide sweeteners are disclosed that are metal complexes of N-[N-(3,3-dimethylbutyl)-L-.alpha.-aspartyl]-L-phenylalanine 1-methyl ester represented by the formula ##STR1## wherein X.sup.p+ is selected from the group consisting of Al.sup.3+, Fe.sup.2+, Fe.sup.3+, Ca.sup.2+, Mg.sup.2+ and Zn.sup.2+ ; Y.sup.q- is selected from the group consisting of Cl.sup.-, SO.sub.4.sup.2-, PO.sub.4.sup.3- and CH.sub.3 COO.sup.- ; x is a number from 1 to 4 and pn=qm. Also disclosed is a liquid low-calorie sweetener containing such metal complexes.
Abstract: Dipeptide sweeteners are disclosed that are sweetener salts of N-[N-(3,3-dimethylbutyl)-L-.alpha.-aspartyl]-L-phenylalanine 1-methyl ester represented by the formula ##STR1## wherein X.sup.m- is a conjugate base derived by deprotonation of an acidic sweetener, preferably saccharin, acesulfame, cyclamic acid and glycyrrhizic acid; and m=n. Also disclosed is a liquid low-calorie sweetener containing such basic salts.
Abstract: This invention relates to the chemical synthesis of N-[N-(3,3-dimethylbutyl)-L-.alpha.-aspartyl]-L-phenylalanine 1-methyl ester using peptide coupling methods. The coupling reaction is conducted by condensation of an activated derivative of novel N-neohexyl-L-aspartic acid with L-phenylalanine or L-phenylalanine methyl ester or by enzymatic coupling of N-neohexyl-L-aspartic acid with L-phenylalanine or L-phenylalanine methyl ester. This invention also relates to novel N-(3,3-dimethylbutyl)-L-aspartic acid, derivatives thereof and the preparation thereof. The activated derivative of N-neohexyl-L-aspartic acid may be an anhydride, mixed anhydride, active ester or an intermediate activated derivative thereof.
Type:
Grant
Filed:
December 24, 1998
Date of Patent:
June 20, 2000
Assignee:
The NutraSweet Company
Inventors:
Indra Prakash, Marie-Christine D. Chapeau
Abstract: This invention provides sweetener blends comprising N-[N-(3,3-dimethylbutyl)-L-.alpha.-aspartyl]-L-phenylalanine 1-methyl ester and another sweetener. The sweetener blends of this invention exhibit isobole synergy.
Abstract: 3,3-Dimethylbutyraldehyde is synthesized via hydrolysis of 1,1-dichloro-3,3-dimethylbutane or 1-bromo-1-chloro-3,3-dimethylbutane in the presence of water and a base and is purified via an aldehyde/bisulfite adduct.
Abstract: This invention provides a method for preparing 3,3-dimethylbutyraldehyde from a tert-butyl cation precursor and vinyl chloride. The tert-butyl cation precursor is contacted with vinyl chloride in the presence of an inorganic acid, and the product is allowed to react with water to form 3,3-dimethylbutyraldehyde.
Abstract: A method is disclosed for preparing 3,3-dimethylbutyraldehyde by using silica gel to isomerize 3,3-dimethyl-1,2-epoxybutane, which in turn may be prepared by oxidation of dimethylbutene. Also disclosed is a method for oxidizing dimethylbutene with dimethyldioxirane to form 3,3-dimethyl-1,2-epoxybutane. The methods provide an economical means of preparing 3,3-dimethylbutyraldehyde.
Type:
Grant
Filed:
July 11, 1997
Date of Patent:
October 26, 1999
Assignee:
The NutraSweet Company
Inventors:
Indra Prakash, Marie-Christine D. Chapeau