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Author Elson, S. W. ♦ Oliver, R. S. ♦ Bycroft, B. W. ♦ Faruk, E. A.
Source J-STAGE
Content type Text
Publisher JAPAN ANTIBIOTICS RESEARCH ASSOCIATION
Language English
Abstract The role of glutamate in clavulanic acid biosynthesis was investigated by feeding DL-[3, $4-^{13}C_{2}]glutamate$ to a Streptomyces clavuligerus fermentation. The DL-[3, $4-^{13}C_{2}]glutamate$ was synthesised by reacting $[2-^{13}C]diethylmalonate$ with $O-tosyl-N-benzoyl-[3-^{13}C]dehydroserine$ ethyl ester, which in turn was synthesised by condensing $[^{13}C]ethylformate$ with N-benzoylglycine ethyl ester. $^{13}C$ NMR examination of the benzyl clavulanate derived from the fermentation revealed the predicted labelling of carbons 2 and 8 with accompanying $^{13}C-^{13}C$ spin-spin coupling. Other enrichments and couplings were observed which could be explained by metabolism of the labelled glutamate via the tricarboxylic acid cycle to give further clavulanic acid precursors. These results confirm that glutamate provides the oxazolidine carbon skeleton as predicted by previous experiments.
ISSN 00218820
Learning Resource Type Article
Publisher Date 1982-01-01
e-ISSN 18811469
Journal The Journal of Antibiotics(antibiotics1968)
Volume Number 35
Issue Number 1
Page Count 6
Starting Page 81
Ending Page 86


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