ISSN:
0170-2041
Keywords:
Oxazolomycin
;
Biosynthesis
;
Streptomyces albus
;
[13C]Precursor
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Feeding experiments with sodium [13C]-labelled acetate, sodium [1-13C]propionate, L-[methyl-13C]methionine, L-[1-13C]-alanine, and [1-13C]glycine on Streptomyces albus (strain JA 3453) produced oxazolomycin (1), whose NMR analysis provided information about the biogenetic construction of its carbon skeleton. Both the (E,E)-diene and the (Z,Z,E)-triene chains are built up from acetate via the polyketide pathway each starting with a glycine-derived building block. The use of glycine predicts an uncommon biosynthetic pathway leading to oxazole rings in actinomycetes. The spiro-ring system in 1 is formed from acetate, glycine, and a C3 unit of unknown origin. The oxazolomycin producing organism combines carbon, oxygen, and nitrogen methylation activity via methionine (C1 pool) for the biosynthesis of 1.
Additional Material:
1 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.199219920178
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