Enzymatic synthesis of L-6-hydroxynorleucine

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-hydroxynor...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry 1999-10, Vol.7 (10), p.2247-2252
Main Authors: Hanson, R L, Schwinden, M D, Banerjee, A, Brzozowski, D B, Chen, B C, Patel, B P, McNamee, C G, Kodersha, G A, Kronenthal, D R, Patel, R N, Szarka, L J
Format: Article
Language:English
Subjects:
Animals
Catalase - chemistry
Catalase - metabolism
Cattle
D-Amino-Acid Oxidase - chemistry
D-Amino-Acid Oxidase - metabolism
Glucose 1-Dehydrogenase
Glucose Dehydrogenases - chemistry
Glucose Dehydrogenases - metabolism
Glutamate Dehydrogenase - chemistry
Glutamate Dehydrogenase - metabolism
Kidney - enzymology
Liver - enzymology
Mitosporic Fungi - enzymology
NAD - metabolism
Norleucine - analogs & derivatives
Norleucine - chemical synthesis
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Summary: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-hydroxyhexanoic acid and L-6-hydroxynorleucine followed by the reductive amination procedure to convert the mixture entirely to L-6-hydroxynorleucine, with yields of 91 to 97% and optical purities of > 99%.
ISSN:0968-0896
DOI:10.1016/S0968-0896(99)00158-3