Contrasteric glycosylations of cotylenol and 1,2-diols by virtual linker selection

12 September 2024, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

Many terpene glycosides exhibit contrasteric patterns of 1,2-diol glycosylation in which the more hindered alcohol bears a sugar; protection of the less hindered alcohol only increases steric repulsion. Here we report a method for contrasteric glycosylation using a new sugar-linker that forms a cleavable, 10-membered ring with high efficiency, leading to syntheses of cotylenin E, J, and ISIR-050. Linker selection was aided by DFT calculations of side reactions and stereoselectivity, as well as conformational analysis using autoDFT, a Python script that converts SMILES strings to DFT-optimized conformational ensembles.

Keywords

glycosylation
cotylenin
14-3-3
linker

Supplementary materials

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Description
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Supporting Information
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Experimental procedures, characterization data, structural assignments, computational details.
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coordinates files
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xyz coordinates from dft calculations
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Supplementary weblinks

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