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Issue 14, 1994
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Synthesis of D-alloisoleucine from L-isoleucine and from (S)-2-methylbutan-1-ol. Synthesis of isostatine

Abstract

Three different synthetic routes to the uncommon α-amino acid D-alloisoleucine were studied. The first was based on the stereospecific inversion of configuration of the C-2 stereogenic carbon of L-isoleucine. The second involved acetylation of L-isoleucine with epimerisation at the C-2 carbon, giving a mixture of L-isoleucine and D-alloisoleucine, which was resolved enzymically with hog kidney acylase. In a new approach, an epimeric mixture of LL-isoleucine and D-alloisoleucine was synthesized from (S)-2-methylbutan-1-ol and was again resolved enzymically. The D-alloisoleucine produced in these syntheses was subsequently transformed into the γ-amino acid isostatine.

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Article information


J. Chem. Soc., Perkin Trans. 1, 1994, 1969-1974
Article type
Paper

Synthesis of D-alloisoleucine from L-isoleucine and from (S)-2-methylbutan-1-ol. Synthesis of isostatine

P. Lloyd-Williams, P. Monerris, I. Gonzalez, G. Jou and E. Giralt, J. Chem. Soc., Perkin Trans. 1, 1994, 1969
DOI: 10.1039/P19940001969

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