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Salvinorin B methoxymethyl ether

Munro, Thomas A., Ho, Douglas M. and Cohen, Bruce M. 2012, Salvinorin B methoxymethyl ether, Acta crystallographica section E, vol. 68, no. Pt 11, pp. o3225-o3226, doi: 10.1107/S1600536812043449.

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Title Salvinorin B methoxymethyl ether
Author(s) Munro, Thomas A.ORCID iD for Munro, Thomas A. orcid.org/0000-0002-3366-7149
Ho, Douglas M.
Cohen, Bruce M.
Journal name Acta crystallographica section E
Volume number 68
Issue number Pt 11
Start page o3225
End page o3226
Total pages 14
Publisher International Union of Crystallography
Place of publication Chester, Eng.
Publication date 2012
ISSN 1600-5368
Summary The title compound [MOM-SalB; systematic name: methyl (2S,4aR,6aR,7R,9S,10aS,10bR)-2-(3-fur-yl)-9-meth-oxy-meth-oxy-6a,10b-dimethyl-4,10-dioxo-2,4a,5,6,7,8,9,10a-octa-hydro-1H-benzo[f]isochromene-7-carboxyl-ate], C(23)H(30)O(8), is a deriv-ative of the κ-opioid salvinorin A with enhanced potency, selectivity, and duration of action. Superimposition of their crystal structures reveals, surprisingly, that the terminal C and O atoms of the MOM group overlap with the corresponding atoms in salvinorin A, which are separated by an additional bond. This counter-intuitive isosterism is possible because the MOM ether adopts the 'classic anomeric' conformation (gauche-gauche), tracing a helix around the planar acetate of salvinorin A. This overlap is not seen in the recently reported structure of the tetra-hydro-pyranyl ether, which is less potent. The classic anomeric conformation is strongly favoured in alk-oxy-methyl ethers, but not in substituted acetals, which may contribute to their reduced potency. This structure may prove useful in evaluating models of the activated κ-opioid receptor.
Language eng
DOI 10.1107/S1600536812043449
Field of Research 030606 Structural Chemistry and Spectroscopy
03 Chemical Sciences
HERDC Research category C1.1 Refereed article in a scholarly journal
ERA Research output type C Journal article
Copyright notice ©2012, International Union of Crystallography
Free to Read? No
Persistent URL http://hdl.handle.net/10536/DRO/DU:30093499

Document type: Journal Article
Collection: School of Life and Environmental Sciences
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