Author:
Frahn JL,Edgar JA,Jones AJ,Cockrum PA,Anderton NA,Culvenor CCJ
Abstract
The corynetoxins,
toxic metabolities of Corynebacterium rathayi
formed in galled seed-heads of infected annual ryegrass, Lolium rigidum, are shown to be new members of the tunicamycin
group of antibiotics. They consist of N-acetylglucosaminyl-tunicaminyl-uracil
in amide linkage with fatty acids which differ in certain respects from those
present in the tunicamycins. The corynetoxin acids
are of slightly longer chain length, C15-C19, occur in a β-hydroxy
as well as saturated and α,β-un-saturated series, and have anteiso, iso and normal chain
terminations. β-Hydroxy acids have not been observed previously in the
tunicamycin group and anteiso chains were reported
only recently in the streptovirudin subgroup.
Stereochemical identity of the C11-aminosugar
in the corynetoxins with the tunicamine
part of the tunicamycins is demonstrated by formation
of a common hydrolysis product, di(N-trifluoro-
acetyl)glucosaminyl-tunicaminyl-uracil. Analysis of
the carbon-13 and proton n.m.r. spectra of the main components, corynetoxins H17a and U17a, confirms the stereochemistry
proposed for tunicamine except that the glycosidic
linkages are changed to α-galactosamine, β-glucosamine.
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36 articles.
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