CHIRAL INTERMEDIATES BY OXIDOREDUCTASES
1359
selective Microbial Reduction of N-(4-(1-Oxo-2-chloroacetyl
Ethyl) Phenyl Methane Sulfonamide, J. Appl. Microbiol Biotech-
nol. 40:241–245 (1993).
[6-Amino-2-[[hydroxy(4-phenylbutyl) phosphinyl]oxy]1-oxo-
hexyl]- -proline, a Novel Orally Active Inhibitor of ACE, J.
Med. Chem. 31:204–212 (1988).
L
12. Hanson, R.L., J. Singh, T.P. Kissick, R.N. Patel, L.J. Szarka, and 30. Haskell, T.H., R. Rodebaugh, N. Plessas, D. Watson, and R.D.
R.H. Mueller, Synthesis of
Hydroxy-Isovalerate Using Leucine Dehydrogenase from Bacil-
lus sp., Bioorg. Chem. 18:116–130 (1990).
L
-β-Hydroxyvaline from α-Keto-β-
Westland, The Preparation and Biological Activity of Novel
Amino Acid Analogs of Butirosin, Carbohydr. Res. 28:263–280
(1973).
13. Hanson, R.L., K.S. Bembenek, R.N. Patel, and L.J. Szarka, Trans- 31. Berezov, T.T., and E.V. Lukasheva, Effect of Substrate and Prod-
-Lysine to CBZ- -Oxylysine Using uct Analogs on the Activity of -Lysine α-Oxidase from Tricho-
formation of N-ε-CBZ-
L
L
L
-
L
Amino Acid Dehydrogenase from Lactobacillus confusus, Appl.
Microbiol. Biotechnol. 37:599–603 (1992).
derma sp., Biochem. Int. 17:529–534 (1988).
32. Jemal, M., and A.I. Cohen, Determination of Enantiomeric Purity
of Z-Oxylysine by Capillary Gas Chromatography, J. Chro-
matogr. 394:388–394 (1987).
14. Ferris, C.D., D.J. Hirsch, B.P. Brooks, and S.H. Snyder, σ-Recep-
tors: From Molecule to Man, J. Neurochem. 57:729–737 (1991).
15. Junien, J.L., and B.E. Leonard, Drugs Acting on σ and Phencycli- 33. Szwajcer, E., P. Brodelius, and K. Mosbach, Production of α-
dine Receptors: A Review of Their Nature, Function, and Possi-
ble Therapeutic Importance, Clin. Neuropharmacol. 12:353–374
(1989).
Keto Acids: 2. Immobilized Whole Cells of Providencia sp. PCM
1298 Containing -Amino Acid Oxidase, Enzyme Microb. Tech-
nol. 4:409–413 (1982).
L
16. Martin, W.R., C.G. Eades, J.A. Thompson, R.E. Huppter, and 34. Meister, A., The α-Keto Analogues of Arginine, Ornithine and
P.E. Gilbert, The Effect of Morphine- and Nalophrine-Like Drugs Lysine, J. Biol. Chem. 206:577–585 (1954).
in the Nondependent and Morphine-Dependent Chronic Spinal 35. Kusakabe, H., K. Kodama, A. Kuninaka, H. Yoshino, H. Misono,
Dog, J. Pharmacol. Exp. Ther. 197:517–530 (1976).
17. Walker, J.M., W.D. Bower, F.O. Walker, R.R. Matsumoto, B.D.
Costa, and K.C. Rice, Sigma Receptors: Biology and Function,
Pharmacol. Rev. 42:355–402 (1990).
18. Steinfels, G.F., S.W. Tam, and L. Cook, Electrophysiological Ef-
fects of Selective σ-Receptor Agonists, Antagonists, and the Se-
lective Phencyclidine Receptor Agonist MK-801 on Midbrain
and K. Soda, A New Antitumor Enzyme, L-Lysine α-Oxidase
from Trichoderma viride. Purification and Enzymological Prop-
erties, Ibid. 255:976–981 (1980).
36. Schütte, H., W. Hummel, and M.R. Kula,
L-2-Hydroxyiso-
caproate Dehydrogenase: A New Enzyme from Lactibacillus con-
fusus for the Stereospecific Reduction of 2-Ketocarboxylic Acids,
Appl. Microbiol. Biotechnol. 19:167–176 (1984).
Dopamine Neurons, Neuropsychopharmacology 2:201–207 37. Pelmont, J., G. Arlaud, and A.M. Rossat, L-Aminoacide oxydases
(1989).
des envelopes des Proteus mirabilis: Properties generales,
Biochimie 54:1359–1374 (1972).
19. Massamiri, T., and S.P. Duckles, Multiple Vascular Effects of
Sigma and PCP Ligands: Inhibition of Amine Uptake and 38. Duerre, J.A., and S. Chakrabarty,
L
-Amino Acid Oxidase of Pro-
teus rettgeri, J. Bacteriol. 121:656–663 (1975).
39. Williams, R.M., Asymmetric Synthesis of
Contractile Responses, J. Pharmacol. Exp. Ther. 253:124–129
(1990).
20. Martinez, J.A., and L. Bueno, Buspirone Inhibits Corticotropin-
Releasing Factor and Stress-Induced Cecal Motor Response in
Rats by Acting Through 5-HT1A Receptors, Eur. J. Pharm.
202:379–383 (1991).
D
-β-Hydroxyvaline, in
Synthesis of Optically Active α-Amino Acids (edited by J.E. Bald-
win and P.D. Magnus), Pergamon, Oxford/New York, 1989, Vol.
7, pp. 185–195.
40. Kamphuis, J., W.H. Boesten, Q.B. Broxterman, H.F.M. Hermes,
J.A.M. van Balken, E.M. Meijer, and H.E. Shoemaker, New De-
velopments in Chemo-Enzymatic Production of Amino Acids,
Adv. Biochem. Eng. Biotechnol. 42:134–186 (1990).
21. Taylor, D.P., M.S. Eison, S.L. Moon, and F.D. Yocca, BMY-
14802: A Potential Antipsychotic with Selective Affinity for σ-
Binding Sites, Adv. Neuropsy. Psychopharm. 1:307–315 (1991).
22. Yevich, J.P., and W.G. Lobeck, Antipsychotic 1-Fluorophenyl- 41. Sykes, R.B., C.M. Cimarusti, D.P. Bonner, K. Bush, D.M. Floyd,
butyl-4-(2-pyrimidinyl)piperazine Derivatives, U.S. Patent
4,605,655 (1986).
23. Yevich, J.P., J.S. New, and D.W. Smith, Synthesis and Biological
Evaluation of 1-(1,2-Benzisothiazol-3-yl)- and (1,2-Benzisoxa-
N.H. Georgopadakou, W.H. Koster, W.C. Liu, W.L. Parker, P.A.
Principle, M.L. Rathnum, W.A. Slusarchyk, W.H. Trejo, and J.S.
Wells, Monocyclic β-Lactam Antibiotics Produced by Bacteria,
Nature (London) 291:489–491 (1981).
zol-3-yl)piperazine Derivatives as Potential Antipsychotic 42. Parker, W.L., J. O’Sullivan, and R.B. Sykes, Naturally Occurring
Agents, J. Med. Chem. 29:359–369 (1986). Monobactams, Adv. Appl. Microbiol. 31:181–205 (1986).
24. Bradford, M.M., A Rapid and Sensitive Method for the Quan- 43. Roemmele, R.C., and H. Rapoport, Chirospecific Synthesis of
titation of Microgram Quantities of Proteins Utilizing the
Principle of Protein Dye Binding, Anal. Biochem. 72:248–254
(1976).
β-Hydroxy-α-Amino Acids, J. Org. Chem. 54:1866–1875
(1989).
44. Ito, Y., M. Sawamura, E. Shirakawa, K. Hayashizaki, and T.
Hayashi, Asymmetric Synthesis of β-Hydroxy-α-alkylamino
Acids by Asymmetric Aldol Reaction of α-Isocyanocarboxy-
lates Catalyzed by Chiral Ferrocenylphosphine-Gold(I) Com-
plexes, Tetrahedron 44:5253–5262 (1988).
25. Larsen, A.A., and P.M. Lish, A New Bio-Isostere: Alkyl-
sulphonamido-Phenethanolamines, Nature 203:1283–1284
(1964).
26. Uloth, R.H., J.R. Kirk, W.A. Gould, and A.A. Larsen, Sulfonali-
dies. I. Monoalkyl- and Arylsulfonamidophenethanolamines. J. 45. Guanti, G., L. Banfi, and E. Narisano, Enantiospecific and Di-
Med. Chem. 9:88–96 (1966)
astereoselective Synthesis of Anti α-Hydrazo- and α-Amino-α-
Hydroxyacids Through “Electrophilic Amination” of β-Hydrox-
yesters, Ibid. 44:5553–5562 (1988).
27. Lish, P.A., J.H. Weikel, and K.W. Dungan, Pharmacological and
Toxicological Properties of Two New β-Adrenergic Receptor An-
tagonists, J. Exp. Ther. 149:161–173 (1965).
28. Somani, P., and T. Bachand, Blockade of Cardiac Effect of Iso-
proterenol by the Stereoisomers of Sotalol, Eur. J. Pharmacol.
7:239–247 (1969).
29. Karanewsky, D.S., M.C. Badia, D.W. Cushman, J.M. DeFor-
rest, T. Dejneka, M.J. Loots, M.G. Perri, E.W. Petrillo, Jr., and
J.R. Powell, (Phosphinyloxy)Acyl Amino Acid Inhibitors of
46. Evans, D.A., E.B. Sjogren, A.E. Weber, and R.E. Conn, Asym-
metric Synthesis of Anti-β-hydroxy-α-amino acids, Tetrahe-
dron Lett. 28:39–42 (1987).
47. Gordon, E.M., M.A. Ondetti, J. Pluscec, C.M. Cimarusti, D.P.
Bonner, and R.B. Sykes, O-Sulfated β-Lactam Hydroxamic Acids
(Monosulfactams). Novel Monocyclic β-Lactam Antiobiotics of
Synthetic Origin, J. Amer. Chem. Soc. 104:6053–6060 (1982).
Angiotensin Converting Enzyme (ACE). 1. Discovery of (S)-1- 48. Parker, W.L., E.M. Cohen, and W.H. Koster, U.S. Patent
JAOCS, Vol. 74, no. 11 (1997)