N-Carbamoyl-L-amino Acid Synthesis
1843
carbamoyl-a-amino acids with Agromyces, Chromobacterium, or Cellulomonas
species. Japan Patent 01228489, 1989; Chem. Abstr. 1990, 112, 156718;
(
m) Aikawa, T.; Takeichi, M.; Tawaki, S.; Tarukawa, H. Manufacture of N-
carbamoyl-D-phenylglycine with Pseudomonas striata from phanylhydantoin.
Japan Patent 01168293, 1989; Chem. Abstr. 1990, 1125, 75316;
(n) Yokozeki, K.; Kubota, K. Enzymic production of D-amino acids from 5-substi-
tuted hydantoins, part III: Mechanism of asymmetric production of D-amino acids
from the corresponding hydantoins by pseudomonas sp. Agr. Biol. Chem. 1987, 51,
7
21–728; (o) Kanegafuchi Chemical Industry. Production of N-carbamoyl-D-a-
amino acids. Japan Patent 81 58493, 1981; Chem. Abstr. 1981, 95, 185549;
p) Takahashi, S.; Ohashi, T.; Kii, Y.; Kumagai, H.; Yamada, H. Microbial trans-
(
formation of hydantoins to amino acids, III: Microbial transformation of hydan-
toins to N-carbamoyl-D-amino acids. J. Ferment. Technol. 1979, 57, 328–332;
(
q) Yoneta, K.; Nagata, T.; Fukumitsu, H.; Yano, Y. D-N-Carbamoylphenylgly-
cine. Japan Patent 79 55788, 1979; Chem. Abstr. 1979, 91, 106622;
r) Yamada, H.; Takahashi, S.; Yoneda, K. D-N-Carbamoyl-a-amino acids.
(
Japan Patent 2757980, 1978; Chem. Abstr. 1979, 90, 4442; (s) Dudley, K. H.;
Roberts, S. B. Dihydropyrimidinase: Stereochemistry of the metabolism of some
5-alkylhydantoins. Drug Metab. Dispos. 1978, 6, 133–139; (t) Viglia, A.;
Fascetti, E.; Perricone, E.; Degen, L. Enzymic complexes suitable for the conver-
sion of racemic hydantoins into optically active amino acids. Ger. Patent 2811303,
1
978; Chem. Abstr. 1979, 90, 2094; (u) Yamada, H.; Takahashi, S.; Yoneta, K.
D-N-Carbamoylphenylglycines. Japan Patent 78 44690, 1978; Chem. Abstr.
978, 89, 74216.
1
7
. (a) Nazaki, H.; Takenaka, Y.; Kira, I.; Watanabe, K.; Yokozeki, K. D-Amino acid
production by E. coli co-expressed three genes encoding hydantoin racemase,
D-hydantoinase and N-carbamoyl-D-amino acid amidohydrolase. J. Mol. Cat.
B—Enzym. 2005, 32, 213–218; (b) Taillades, J.; Boiteau, L.; Beuzelin, I.;
Lagrille, O.; Biron, J. P.; Vayaboury, W.; Vandenabeele-Trambouze, O.;
Giani, O.; Commeyras, A. A pH-dependent cyanate reactivity model: Application
to preparative N-carbamoylation of amino acids. J. Chem. Soc., Perkin Trans. 2
2001, 1247–1254; (c) Smyth, D. G. Carbamoylation of amino and tyrosine
hydroxyl groups: Preparation of an inhibitor of oxytocin with no intrinsic
activity on the isolated uterus. J. Biol. Chem. 1978, 242, 1579–1591;
d) Gopko, V. F.; Shustova, N. D.; Anoshina, G. M.; Zubova, T. E.;
(
Radina, L. B. Synthesis and study of a-(nitrosoureido)carboxylic acids with
potential antineoplastic activity. Khim.-Farm. Zh. 1978, 12, 53; Chem. Abstr.
1978, 89, 146399; (e) Williams, A.; Jencks, W. P. Urea synthesis from amines
and cyanic acid: Kinetic evidence for a zwitterionic intermediate. J. Chem. Soc.,
Perkin Trans. 1974, 2, 1753–1759; (f) Gustafsson, H.; Ragnarsson, U. New
route of a-hydrazinopropionic acid of high optical purity. Acta Pharm. Suec.
1
974, 11, 493–494; (g) Bayerlein, F.; Kolbeck, W.; Stark, A. Cysteine
N-carbamide. Ger. Patent 1518734, 1973; Chem. Abstr. 1973, 89, 137500;
h) Suzuki, T.; Igarashi, K.; Hase, K.; Tuzimura, K. Optical rotatory dispersion
and circular dichroism of amino acid hydantoins. Agric. Biol. Chem. 1973, 37,
11–416; (i) Diamalt, A.-G. N-Carbamides of amino acids containing thiol
groups, for treating hyperviscous pituita. Fr. Pat. M. 6492, 1969; Chem. Abstr.
971, 75, 36679; (j) Stark, A.; Kolbeck, W.; Bayerlein, F. N-Carbamoylcysteine.
(
4
1
Brit. Patent 1161029, 1969; Chem. Abstr. 1969, 71, 128766; (k) Beecham Group
Ltd. Substituted 6-aminopenicillanic acids. Neth. Patent Appl. 6509544, 1966;
Chem. Abstr.; 1966, 65, 3883c,; (l) Dakin, H. D. Constitution of allantoin and