Chemistry: molecular biology and microbiology – Micro-organism – tissue cell culture or enzyme using process... – Preparing alpha or beta amino acid or substituted amino acid...
Patent
1998-01-26
1999-07-27
Lilling, Herbert J.
Chemistry: molecular biology and microbiology
Micro-organism, tissue cell culture or enzyme using process...
Preparing alpha or beta amino acid or substituted amino acid...
435109, 435110, 435197, C12P 1304, C12P 1314, C12P 1320
Patent
active
059289090
ABSTRACT:
The regioselective and chemoselective hydrolysis of an .alpha.-ester group of an amino acid diester using pig liver esterase enzyme (PLE) is disclosed. The amino acid diesters may be either N-protected or unprotected and the diester groups may be the same or different. In particular, the preparation of a number of .gamma.-ester glutamates and .beta.-ester aspartates are provided.
REFERENCES:
Wiecozorek, W. et al., ".alpha.-Hydroxymethylaspartic acid: Synthesis and absolute configuration by X-ray analysis of its derivative (+)-4 benzoylamino-4-carboxy-.gamma.-butyrolactone," J. Crystallogr. Spectrosc. Res., 1991, 21, 107.
Liu, K.-C. et al., "Synthesis of N-Substituted .beta.-Methyl DL-Aspartates as Potential Hypocholesteremics," Arch. Pharmaz., 1975, 308, 564.
Bodanszky, M., "Principals of Peptide Synthesis," (Springer-Verlag), 1984, 84-89.
Bodanszky, M. et al., "The Practice of Peptide Synthesis" (Springer-Verlag), 1984, 12, 13 and 20.
Ohfune, Y. et al., "An Efficient One-Step Reductive N-Monoalkylation of .alpha.-Amino Acids," Chem. Letters, 1984, 441.
Stein, Karin A., et al., "Enzyme catalyzed regioselective hydrolysis of aspartate diesters," Chemical Abstracts, vol. 1996, Abstract No. 220614, Columbus, Ohio, US.
Prakash, Indra et al., "Pig liver esterase catalyzed regio- and chemoselective hydrolysis of amino acid diesters," Chemical Abstracts, vol. 1996, Abstract No. 415167, Columbus, Ohio, US.
Ohno, M. and Otsuka, M., "Chiral Synthons By Ester Hydrolysis Catalyzed By Pig Liver Esterase," Organic Reactions, 1989, vol. 37, Chapter 1.
Hultin, P.G. et al., "Enzymes in Organic Synthesis. 48. Pig Liver Esterase and Porcine Pancreatic Lipase Catalyzed Hydrolyses of 3,4-(Isopropylidenedioxy)-2,5-tetrahydrofuranyl Diesters," J. Org. Chem., 1991, 56, 5375.
Kobayashi S. et al., "The First Enantioselective Synthesis of Fortamine, the 1,4-Diaminocyclitol Moiety of Fortimicin A, by Chemicoenzymatic Approach," J. Org. Chem., 1990, 55, 1169.
Adachi, K. et al., "Chiral Synthons by Enantioselective Hydrolysis of meso-Diesters with Pig Liver Esterase: Substrate-Stereoselectivity Relationships," Chima, 1986, 40, 311.
Stein, K.A. et al., "Enzyme-Catalyzed Regioselective Hydrolysis of Asparate Diesters," J. Org. Chem., 1995, 60, 8110.
Albert, R. et al., "A Simple and Convenient Synthesis of .beta.-Aspartates and .gamma.- Glutamates," Synthesis, 1987, 635.
Metz, P., "Preparation of Enantiomerically Pure 3-Endo-Sulfonylmethyl 1989, vol. 45, 1989, 7311.
Van der Eycken, J., et al., "Enzymatic Preparation of Optically Active Products. An Attractive Alternative to Enantioselective Diels-Alder Syntheses," J. Chem. Soc., Chem. Commun., 1989, 306.
Sabbioni, G. et al., "Enzymes in Organic Synthesis. 39. Preparation of Chiral Cyclic Acid-Esters and Bicyclic Lactones via Stereoselective Pig Liver Esterase Catalyzed Hydrolyses of Cyclic Meso Diesters," J. Org. Chem. 52, 1987, 4565.
Sabbioni, G. et al., "Preparations of Bicyclic Chiral Lactone Synthons via Stereospecific Pig Liver Esterasecatalysed Hydrolyses of meso-Diesters. Ring-size induced Reversal of Stereospecificity," J. Chem. Soc., Chem. Commun., 1984, 236.
Jongejan, J.A. and Duine, J.A., "Enzymatic Hydrolysis of Cyclopropyl Acetate, A Facile Method for Medium- and Large-Scale Preparations of Cyclopropanol," Tetrahedron Lett., 1987, 28, 2767.
Hazato, A. et al., "Hydrolysis of Prostaglandin E.sub.1 Methyl Ester and Analogues with Pig Liver Esterase," Nippon Kagaku Kaishi 1983, 9, 1390; Chem. Abstr.,1984, 100, 120720q.
Swann, Jr. S. et al., "Ethyl Hydrogen Sebacate," Org. Syntheses Coll. vol. II, 1943, 276.
March, J., Advanced Organic Chemistry, Third Ed. 1985, 347.
Durham, L.J. et al., J., "Methyl Hydrogen Hendecanedioate," Org. Syntheses Coll. vol. IV, 1963, 635.
Prestidge, R.L. et al., "A Novel High-Yield Synthesis of .gamma. Esters of Glutamic Acid and .beta. Esters of Aspartic Acid by the Coppert-Catalyzed Hydrolysis of Their Diesters," J. Org. Chem., 1975, 40, 3287.
Guibe-Jampel, E. et al., "Enantioselective Hydrolysis of Racemic Diesters by Porcine Pancreatic Lipase," J. Chem. Soc., Chem. Commun., 1987, 1080.
Miyazawa, T. et al., "Optical Resolution of Unusual Amino-Acids by Lipase-catalysed Hydrolysis," J. Chem. Soc., Chem. Commun., 1988, 1214.
Cohen, S.G. et al., "Action of .alpha.-Chymotrypsin on Diethyl N-Acetyl-aspartate," Biochemistry, 1963, 2, 820.
Cohen, S.G. et al., "Kinetics of Hydrolysis of Dicarboxylic Esters and Their .alpha.-Acetamido Derivatives by .alpha.-Chymotrypsin," J. Am. Chem. Soc., 1964, 86, 4999.
Chung-gi Shin, et al., "Dehydrooligopeptides. XIII. Selective Enzymatic Hydrolysis of N-Protected .alpha.-Dehydroglutamic Acid Diesters and Their Analogs Using Papain as Catalyst," Bulletin Chemical Society of Japan, vol. 64, No. 12, 1991, pp. 3575-3580.
Chen, S.T. et al., "The Synthesis of .beta.-Benzyl L-Aspartate and .gamma.-Benzyl L-Glutamate by Enzyme-Catalyzed Hydrolysis," J. of Synth. Organic Chem., Synthesis, 1987, 581.
Pugniere, M. et al., "Enzymatic Synthesis of Side Chain Benzyl Esters of L-.alpha.-Amino Dicarboxylic Acids,", Tetrahedron: Asymmetry, 1992, 3, 1015.
Roeske, R., J., "Preparation of t-Butyl Esters of Free Amino Acids," J. of Org.Chem. 28, 1963, 1251.
Oki, K. et al., "The Resolution of N-Benzyloxylcarbonyl-DL-amino Acids Using Ephedrine," Bull. Chem. of the Society of Japan, 43, 1969, 2554.
Marchatti, E., Ann. Chim., 1967, 57. 624.
Ager David J.
Pantaleone David P.
Prakash Indra
Lilling Herbert J.
NSC Technologies LLC
LandOfFree
Regioselective .alpha.-hydrolysis of amino acid diesters using p does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Regioselective .alpha.-hydrolysis of amino acid diesters using p, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Regioselective .alpha.-hydrolysis of amino acid diesters using p will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-877691