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Natural Product Research
Formerly Natural Product Letters
Volume 33, 2019 - Issue 20
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Short Communications

A problem in the structure assignment of acremolin C, which is most probably identical with acremolin B

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Pages 3011-3015 | Received 16 May 2018, Accepted 05 Aug 2018, Published online: 16 Nov 2018
 

Abstract

With the help of chemical shifts computed with density functional theory (DFT), it is demonstrated that the reported experimental 13C NMR data of acremolin C are incompatible with the claimed structure of an N2,3-ethenoguanine with an isopropyl group at C-1'. An alternative structure, which is in agreement with both experimental and computed data, presents an isopropyl group at the C-2' position of an N2,3-ethenoguanine and leads to the conclusion that acremolin C is identical with acremolin B.

Graphical Abstract

Acknowledgement

Computer support from the US National Science Foundation (XSEDE Program; CHE-030089) is gratefully acknowledged.

Disclosure statement

No potential conflict of interest was reported by the authors.

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