Enzymatic synthesis of L-6-hydroxynorleucine

…, MD Schwinden, A Banerjee, DB Brzozowski…

Index: Hanson, Ronald L.; Schwinden, Mark D.; Banerjee, Amit; Brzozowski, David B.; Chen, Bang-Chi; Patel, Bharat P.; McNamee, Clyde G.; Kodersha, Gus A.; Kronenthal, David R.; Patel, Ramesh N.; Szarka, Laszlo J. Bioorganic and Medicinal Chemistry, 1999 , vol. 7, # 10 p. 2247 - 2252

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Citation Number: 77

Abstract

l-6-Hydroxynorleucine, a key chiral intermediate used for synthesis of a vasopeptidase inhibitor, was prepared in 89% yield and> 99% optical purity by reductive amination of 2- keto-6-hydroxyhexanoic acid using glutamate dehydrogenase from beef liver. In an alternate process, racemic 6-hydroxynorleucine produced by hydrolysis of 5-(4-hydroxybutyl) hydantoin was treated with d-amino acid oxidase to prepare a mixture containing 2-keto-6 ...