The Journal of Antibiotics
Online ISSN : 1881-1469
Print ISSN : 0021-8820
ISSN-L : 0021-8820
Biosynthesis of Lactacystin
SENJI TAKAHASHIKENICHI UCHIDAAKIRA NAKAGAWAYOKO MIYAKEMASATSUNE KAINOSHOKEIICHI MATSUZAKISATOSHI OMURA
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1995 Volume 48 Issue 9 Pages 1015-1020

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Abstract

The biosynthesis of lactacystin, a new microbial metabolite which induces differentiation of neuroblastoma cells, was studied by the feeding experiments of various 13C-labeled compounds and NMR spectroscopic analysis. The feeding experiments showed that lactacystin consists of three biosynthetic units, namely isobutyrate (and/or L-valine), L-leucine and L-cysteine. The C10 unit containing γ-lactam moiety arises by a condensation between methylmalonic semialdehyde and Cα position of L-leucine, followed by intramolecular cyclization. Two diastereotopic methyls, C-11 and C-12 of lactacystin were found to originate from the pro-R and pro-S methyls of leucine, respectively, as shown by incorporating a new type of chiral 13C-labeled L-leucine.

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© Japan Antibiotics Research Association
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