Biosynthesis of Cylindrospermopsin

Studies on the biosynthesis of cylindrospermopsin (1), a potent hepatotoxin associated with the cyanobacterium Cylindrospermopsis raciborskii, indicate that 1 is an acetogenin with guanidinoacetic acid serving as the starter unit of the polyketide chain. Feeding experiments show that C14 and C15 of...

Full description

Saved in:
Bibliographic Details
Published in:Journal of organic chemistry 2000-01, Vol.65 (1), p.152-156
Main Authors: Burgoyne, David L, Hemscheidt, Thomas K, Moore, Richard E, Runnegar, Maria T. C
Format: Article
Language:English
Subjects:
Alkaloids - biosynthesis
Bacterial Toxins
Cyanobacteria - metabolism
Magnetic Resonance Spectroscopy
Models, Molecular
Molecular Structure
Uracil - analogs & derivatives
Uracil - biosynthesis
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Studies on the biosynthesis of cylindrospermopsin (1), a potent hepatotoxin associated with the cyanobacterium Cylindrospermopsis raciborskii, indicate that 1 is an acetogenin with guanidinoacetic acid serving as the starter unit of the polyketide chain. Feeding experiments show that C14 and C15 of 1 are derived from C1 and C2 of glycine, respectively, and C4 through C13 arise from five contiguous acetate units attached head to tail. The methyl carbon on C13 originates from the C1 pool. The starter unit, established by the incorporation of [guanidino-13C,α-15N]-guanidinoacetic acid into N16 and C17 of 1, does not appear to be formed from glycine by known amidination pathways. The origin of the NH−CO−NH segment in the uracil ring is also unknown.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo991257m