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A butenolide intermediate in methylenomycin furan biosynthesis is implied by incorporation of stereospecifically C-13-labelled glycerols

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Corre, Christophe, Haynes, Stuart W., Malet, Nicolas, Song, Lijiang and Challis, Gregory L.. (2011) A butenolide intermediate in methylenomycin furan biosynthesis is implied by incorporation of stereospecifically C-13-labelled glycerols. Chemical Communications, Vol.46 (No.23). pp. 4079-4081. ISSN 1359-7345

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Official URL: http://dx.doi.org/10.1039/c000496k

Abstract

The label from [3-C-13]-L-glycerol is incorporated into the hydroxymethyl group of methylenomycin furans suggesting a butenolide intermediate in their biosynthesis.

Item Type:

Journal Article

Subjects:

Q Science > QD Chemistry
Q Science > QR Microbiology

Divisions:

Faculty of Science > Chemistry

Library of Congress Subject Headings (LCSH):

Streptomyces coelicolor, Antibiotic-producing organisms, Streptomycin, Biosynthesis, Furans

Journal or Publication Title:

Chemical Communications

Publisher:

Royal Society of Chemistry

ISSN:

1359-7345

Official Date:

2011

Dates:

Date	Event
2011	Published

Volume:

Vol.46

Number:

No.23

Number of Pages:

Page Range:

pp. 4079-4081

Identification Number:

10.1039/c000496k

Status:

Peer Reviewed

Publication Status:

Published

Access rights to Published version:

Restricted or Subscription Access

Funder:

Biotechnology and Biological Sciences Research Council (Great Britain) (BBSRC)

Grant number:

BB/E008003/1 (BBSRC)

References:

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9 Intramolecular proton transfer to the acetylene in 4 would generate
an alternative allene intermediate, which could also undergo loss of
formaldehyde to yield an enolate.