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Natural cis-solamin is a mixture of two tetra-epimeric diastereoisomers: biosynthetic implications for annonaceous acetogenins

Natural cis-solamin is a mixture of two tetra-epimeric diastereoisomers: biosynthetic implications for annonaceous acetogenins
Natural cis-solamin is a mixture of two tetra-epimeric diastereoisomers: biosynthetic implications for annonaceous acetogenins
The anti-tumour natural product cis-solamin has been shown to occur as a mixture two of tetra-epimeric diastereoisomers 1A and 1B whereas solamin (6) was isolated as a single diastereoisomer; the biosyntheses of 1A/B and 6 are likely to involve enzyme-mediated cyclohydrations of the bis-epoxide acetogenins anti-diepomuricanin A2 and syn-diepomuricanin A1 respectively, where addition of water occurs regioselectively at either C15 or C20.
annonaceous acetogenin, cis-solamin
1477-0520
1217-1219
Hu, Yulai
5f6957ca-475f-42b3-892f-e2d64cf2ef11
Cecil, Alex R.L.
85c727e5-86ae-4dd1-adfd-74671ffa213e
Frank, Xavier
1ca329b6-b9f7-467c-be7a-eee02d3c4dcc
Gleye, Christophe
40da7abd-021b-469e-b9d7-05fe6b7b539e
Figadère, Bruno
a2e2bc0e-7a42-4ca2-86bf-41dab616aeea
Brown, Richard C.D.
21ce697a-7c3a-480e-919f-429a3d8550f5
Hu, Yulai
5f6957ca-475f-42b3-892f-e2d64cf2ef11
Cecil, Alex R.L.
85c727e5-86ae-4dd1-adfd-74671ffa213e
Frank, Xavier
1ca329b6-b9f7-467c-be7a-eee02d3c4dcc
Gleye, Christophe
40da7abd-021b-469e-b9d7-05fe6b7b539e
Figadère, Bruno
a2e2bc0e-7a42-4ca2-86bf-41dab616aeea
Brown, Richard C.D.
21ce697a-7c3a-480e-919f-429a3d8550f5

Hu, Yulai, Cecil, Alex R.L., Frank, Xavier, Gleye, Christophe, Figadère, Bruno and Brown, Richard C.D. (2006) Natural cis-solamin is a mixture of two tetra-epimeric diastereoisomers: biosynthetic implications for annonaceous acetogenins. Organic & Biomolecular Chemistry, 4, 1217-1219. (doi:10.1039/b601943a).

Record type: Article

Abstract

The anti-tumour natural product cis-solamin has been shown to occur as a mixture two of tetra-epimeric diastereoisomers 1A and 1B whereas solamin (6) was isolated as a single diastereoisomer; the biosyntheses of 1A/B and 6 are likely to involve enzyme-mediated cyclohydrations of the bis-epoxide acetogenins anti-diepomuricanin A2 and syn-diepomuricanin A1 respectively, where addition of water occurs regioselectively at either C15 or C20.

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More information

Published date: 2006
Keywords: annonaceous acetogenin, cis-solamin

Identifiers

Local EPrints ID: 44157
URI: http://eprints.soton.ac.uk/id/eprint/44157
ISSN: 1477-0520
PURE UUID: 88ca82c9-e28c-491a-b41b-00905235f210
ORCID for Richard C.D. Brown: ORCID iD orcid.org/0000-0003-0156-7087

Catalogue record

Date deposited: 19 Feb 2007
Last modified: 10 Dec 2019 01:53

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