Industrial Biotransformations

Amidase
Klebsiella terrigena
6) Literature
EC 3.5.1.4
● Aebischer, B., Frey, P., Haerter, H.-P., Herrling, P. L., Mueller, W., Olverman, H. J., Watkins, J.
C. (1989) Synthesis and NMDA antagonistic properties of the enantiomers of 4-(3-phosphonopropyl)piperazine-2-carboxylic
acid (CPP) and of the unsaturated analogue (E)-4-(3-phosphonoprop-2-enyl)piperazine-2-carboxylic
acid (CPP-ene), Helv. Chim. Acta 72, 1043–1051
● Askin, D., Eng, K. K., Rossen, K., Purick, R. M., Wells, K. M., Volante, R. P., Reider, P. J.
(1994) Highly diastereoselective reaction of a chiral, non-racemic amide enolate with (S)-glycidyl
tosylate. Synthesis of the orally active HIV-1 protease inhibitor l-735,524, Tetrahedron Lett.
35, 673–676
● Bigge, C. F., Johnson, G., Ortwine, D. F., Drummond, J. T., Retz, D. M., Brahce, L. J.,
Coughenour, L. L., Marcoux, F. W., Probert Jr., A. W. (1992) Exploration of N-phosphonoalkyl-,
N-phosphonoalkenyl-, and N-(phosphonoalkyl)phenyl-spaced α-amino acids as competitive
N-methyl-d-aspartic acid antagonists, J. Med. Chem. 35, 1371–1384
● Bruce, M. A., St Laurent, D. R., Poindexter, G. S., Monkovic, I., Huang, S., Balasubramanian,
N. (1995) Kinetic resolution of piperazine-2-carboxamide by leucine aminopeptidase. An application
in the synthesis of the nucleoside transport blocker (–)Draflazine, Synth. Commun. 25,
2673–2684
● Eichhorn, E., Roduit, J.-P., Shaw, N., Heinzmann, K., Kiener, A. (1997) Preparation of (S)piperazine-2-carboxylicacid,
(R)-piperazine-2-carboxylic acid, and (S)-piperidine-2-carboxylic
acid by kinetic resolution of the corresponding racemic carboxamides with stereoselective amidase
in whole bacterial cells, Tetrahedron Asymm. 8, 2533–2536
● Kiener, A., Roduit, J.-P., Kohr, J., Shaw, N. (1995) Biotechnologisches Verfahren zur Herstellung
von cyclischen (S)-α-Aminocarbonsäuren und (R)-α-Aminocarbonsäureamiden, Lonza
AG, EP 0686698 A2
● Kiener, A., Roduit, J. P., Heinzmann, K. (1996) Biotechnical production process of piperazine
(R)-α-carboxylic acids and piperazine (S)-α-carboxylic acid amide, Lonza AG, WO 96/35775
● Petersen, M., Kiener, A.(1999) Biocatalysis: Preparation and functionalization of N-heterocycles,
Green Chem. 2, 99–106
● Shiraiwa, T., Shinjo, K., Kurokawa, H. (1991) Asymmetric transformations of proline and
2-piperidinecarboxylic acid via formation of salts with optically active tartaric acid, Bull. Chem.
Soc. Jpn. 64, 3251–3255
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