| Download | - View final version: Use of ¹³C in biosynthetic studies. Incorporation of ¹³C-labeled acetate into chartreusin by Streptomyceschartreusis (PDF, 401 KiB)
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| DOI | Resolve DOI: https://doi.org/10.1139/v77-335 |
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| Author | Search for: Canham, P. L.; Search for: Vining, L. C.; Search for: McInnes, A. G.1; Search for: Walter, J. A.1; Search for: Wright, J. L. C.1 |
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| Affiliation | - National Research Council of Canada. Atlantic Regional Laboratory
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| Format | Text, Article |
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| Abstract | Examination by ¹³C nuclear magnetic resonance spectroscopy of chartreusin produced in cultures of Streptomyceschartreusis supplemented with [1-¹³C] and [2-¹³C]acetate showed that the 19-carbon aglycone component was derived entirely from acetate. In the spectrum of chartreusin enriched from [1,2-¹³C]acetate the signals for 16 of the carbon atoms were accompanied by satellites due to spin–spin coupling of intact ¹³C—¹³C units. The coupled pairs were matched with the aid of homonuclear single ¹³C-frequency decoupling. Of the uncoupled carbon atoms, two were derived from methyl groups of acetate and the third came from an acetate carboxyl group. The arrangement of paired and unpaired ¹³C atoms in chartreusin suggests that the aglycone is derived from a single 22-carbon polyketide chain. Cyclization to a benzpyrene-like intermediate followed by ring cleavage and loss of three carbon atoms provides a plausible route from the polyketide to the substituted isocoumarin structure of the aglycone. |
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| Publication date | 1977-06-15 |
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| Publisher | Canadian Science Publishing |
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| In | |
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| Language | English |
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| Peer reviewed | Yes |
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| Identifier | NRCC-15895 |
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| Export citation | Export as RIS |
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| Report a correction | Report a correction (opens in a new tab) |
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| Record identifier | cab6c8ad-ca81-4bab-82c3-214dc48bddf2 |
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| Record created | 2023-09-14 |
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| Record modified | 2023-09-14 |
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