13C labeling indicates that the epoxide-containing amino acid of HC-toxin is biosynthesized by head-to-tail condensation of acetate

Y Q Cheng; L D Le; J D Walton; K D Bishop

doi:10.1021/np980209e

13C labeling indicates that the epoxide-containing amino acid of HC-toxin is biosynthesized by head-to-tail condensation of acetate

J Nat Prod. 1999 Jan;62(1):143-5. doi: 10.1021/np980209e.

Authors

Y Q Cheng¹, L D Le, J D Walton, K D Bishop

Affiliation

¹ Department of Energy-Plant Research Laboratory and Department of Chemistry, Michigan State University, East Lansing, Michigan 48824, USA.

PMID: 9917303
DOI: 10.1021/np980209e

Abstract

HC-toxin, cyclo(D-Pro-L-Ala-D-Ala-L-Aeo), where Aeo stands for 2-amino-9,10-epoxi-8-oxodecanoic acid, is a potent inhibitor of histone deacetylase. Previous molecular genetic studies indicated that HC-toxin biosynthesis requires a dedicated fatty acid synthase. The incorporation of [13C]acetate into HC-toxin was studied using NMR. The pattern of incorporation of 13C was consistent with the carbons of Aeo being derived from head-to-tail condensation of acetate.

Publication types

Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.
Research Support, U.S. Gov't, P.H.S.

MeSH terms

Acetates / metabolism*
Amino Acids / biosynthesis*
Amino Acids / chemistry
Epoxy Compounds / chemistry*
Fungi / metabolism
Magnetic Resonance Spectroscopy
Peptides, Cyclic / chemistry*
Protein Conformation
Toxins, Biological / chemistry

Substances

Acetates
Amino Acids
Epoxy Compounds
Peptides, Cyclic
Toxins, Biological
HC toxin