.alpha.-Oxiranyl amino acids and their synthesis

Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...

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549524, 549525, 562553, 562564, C07D30102, C07C20500

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active

060083867

ABSTRACT:
The present invention is related to a novel class of decarboxylase enzyme inhibitors consisting of .alpha.-oxiranyl amino acids and derivatives thereof and a method of synthesizing such compounds.

REFERENCES:
patent: 3960927 (1976-06-01), Metcalf et al.
patent: 4147873 (1979-04-01), Metcalf et al.
patent: 4183858 (1980-01-01), Metcalf et al.
patent: 4418075 (1983-11-01), Tamai et al.
patent: 5190969 (1993-03-01), Blumenstein et al.
patent: 5705660 (1998-01-01), Berkowitz et al.
Kochetkov et al., Organic Chemistry of Nucleic Acids, Part A, Plenum Press, New York, 1971, pp. 334-338 & 347-348. Month of publication data is unavailable.
Kochetkov et al., Organic Chemistry of Nucleic Acids, Part B, Plenum Press, New York, 1972, pp. 412-419 & 423. Month of publication data is unavailable.
Kochetkov et al., Organic Chemistry of Nucleic Acids, Part B, Plenum Press, New York, 1972, pp. 466-470 & 475-476. Month of publication data is unavailable.
Berkowitz et al., Enantiomerically Enriched .alpha.-Vinyl Amino Acids Via Lipase-Mediated "Reverse Transesterification", Tetrahedron Letters, vol. 35, No. 47, p. 8743-8746 (1994). Month of publication data is unavailable.
Berkowitz et al., Enantiomerically Enriched .alpha.-Methyl Amino Acids. Use of an Acyclic, Chiral Alanine-Derived Dianion with a High Diastereofacial Bias, American chemical Society, vol. 60, No. 5, p. 1233-1238 (1995). Month of publication data is unavailable.
Berkowitz et al., Free .alpha.-Oxiranyl Amino Acids, Journal of Organic Chemistry, vol. 60, No. 17, p. 5368-5369 (1995). Month of publication data is unavailable.
Berkowitz et al., A Convenient Synthesis of L-.alpha.-Vinylglycine from L-Homoserine Lactone, Synthesis p. 39-42. (Issue No. 1, Jan. 1996).
Berkowitz et al., Synthesis of Higher .alpha.-Chlorovinyl and .alpha.-Bromovinyl Amino Acids: The Amino Protecting Group Determines the Reaction Course, Tetrahedron Letters, vol. 37, No. 25, p. 4309-4312 (1996). Month of publication data is unavailable.
Berkowitz et al., .alpha.-Vinyllysine and .alpha.-Vinylarginine are Time-Dependent Inhibitors of Their Cognate Decarboxylases, Bioorgainic & Medicinal Chemistry Letters, vol. 6, No. 18, p. 2151-2156 (1996). Month of publication data is unavailable.
Berkowitz, D. B. and Pedersen M. L., "Simultaneous Amino and Carboxyl Group Protection for .alpha.-Branched Amino Acids", Journal of Organic Chemistry vol. 59, (1994).(Issue No. 18), 5476-5478 (Sep. 9, 1994).
Berkowitz, D. B. and Pedersen, M. L., "Formal .alpha.-Vinylation of Amino Acids. Use of a New Benzeneselenolate Equivalent", Journal of Organic Chemistry 58:6966-6975 (1993). (Issue No. 25) Month of publication data is unavailable.
Yarlett, N., et al., "Inhibition of Trichomonas Vaginalis Ornithine Decarboxylase By Amino Acid Analogs," Biochem. Pharamacology 44:243-250 (1992). (Issue No. 2) Month of publication data is unavailable.
Chenault, H.K.; Dahmer, J.; Whitesides, G.M. "Kinetic Resolution of Unnatural and Rarely Occurring Amino Acids: Enantioselective Hydrolysis of N-Acyl Amino Acids Catalyzed by Acylase I", J.Am.Chem.Soc. 111:6354-6364 (1989). (Issue No. 16) Month of publication data is unavailable.
Sailer, M.; Sasek, V.; Sejbal, J.; Budesinky, M.; Musilek, V. "Flavovirin-A New Antifungal Antibiotic Produced by the Pyrenomycete Melanconis flavovirens", J. Basic Microbiol. 29:375-381(1989).(Issue No. 6) Month of publication data is unavailable.
Castelhano, A. L., et al, "Synthesis of .alpha.-Amino Acids with .beta.,.gamma.-Unsaturated Side Chains", Tetrahedron 44:5451-5466 (1988). (Issue No. 17) Month of publication data is unavailable.
Kashino, S., et al., "Structures of 3.beta.- and 17 .beta.-Oxirane Inhibitors of 3-Oxo-.DELTA..sup.5 -steroid Isomerase", J. Am. Chem.Soc. 109:6765-6771 (1987). (Issue No. 22) Month of publication data is unavailable.
Sawada, S. et al., "Synthesis of Labeled (.+-.)-2-Amino-3-butenoic Acids", J. Org. Chem. 51:3384-86 (1986). (Issue No. 17) Month of publication data is unavailable.
Fitzner, J.F., et al., "Synthesis of Protected Racemic .beta.,.gamma.-Unsaturated-60 -Unsaturated .alpha.-Amino Acids via .gamma.-Phenylseleno-.alpha., .beta.-Unsaturated Esters", Tetrahedron Lett. 26:1959-1962 (1985). (Issue No. 16). Month of publication data is unavailable.
Kim, S.; Lee, J.E.; Kim, Y.C., "A Simple and Mild Esterification Method for Carboxylic Acids Using Mixed Carboxylic-Carbonic Anhydrides", J. Org. Chem. 50:560-565 (1985).(Issue No. 5).
Neubauer, H. J.; Baeze, J.; Freer, J. and Schollkopf, "Asymmetric Synthesis of an Amino Acid Ester with a 3,4-Epoxy Function (.beta.,.gamma.-Epoxy Function) by the Bislactim Ether Method," Liebigs Ann. Chem. 1508-1511 (1985).
Murray-Rust, P., et al., "Directional Hydrogen Bonding to sp.sup.2 - and sp.sup.3 -Hybridized Oxygen Atoms and Its Relevance to Ligand-Macromolecule Interactions," J. Am. Chem. Soc. 106:1018-1025 (1984). (Issue No. 4).
Danzin, C., et al., ".alpha.-Ethynyl and .alpha.-Vinyl Analogues of Ornithine as Enzyme-Activated Inhibitors of Mammalian Ornithine Decarboxylase," J. Med. Chem. 24:16-20 (1981). (Issue No. 1) Month of publication data is unavailable.
Huldrik P.F. et al., ".alpha.-Silyl Aldehydes: Preparation and Use As Stereoselective Vinyl Cation Equivalents", J. Am. Chem.Soc. 103:6251-53 (1981). (Issue No. 20). Month of publication data is unavailable.
Steglich, W. et al, "Uberfuhrung von Aminosauren in .alpha.-Vinylaminosauren", Synthesis 481-83 (1980). (Jun.).
Metcalf, B.W., et al., "Phenyl trans-2-Chlorovinyl Sulphone", J. Chem. Soc. Chem. Commun. 914-15 (1978). Month of publication data is unavailable.
Metcalf, B.W., et al., "Synthesis of .beta.,.gamma.-Unsaturated Amino Acids as Potential Catalytic Irreversible Enzyme Inhibitors." Tetrahedron Lett. 3689-3692 (1978). (Issue No. 41) Month of publication data is unavailable.
Taub, D., et al., "Syntheses of .alpha.-Ethynyl-3,4-Dihydroxyphenylalanine and .alpha.-Vinyl-3,4-Dihydroxypenylalanine." Tetrahedron Lett. 2745-2748 (1977).(Issue No. 32) Month of publication data is unavailable.
Turk, J., et al., "Studies with .alpha.-Methyl Amino Acids. Resolution and Amino Protection", J. Org. Chem. 40:953-955 (1975). (No. 7). Month of publication data is unavailable.
Cook, C.E. et al., "Steroids. LXXIX. Synthesis and Reactions of Oxiranes Obtained from 3- and 17-Keto Steroids", J. Organic Chem. 33:2789-2793 (1968). (Issue No. 7, Jul. 1968).

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