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Carbohydrate transition state mimics: synthesis of imidazolo-pyrrolidinoses as potential nectrisine surrogates.

Abstract：

:The syntheses of four glyco-imidazoles, which are pentose-derivatives belonging to the D-series, as well as the syntheses of their L-enantiomers, are reported. Starting from the known linear xylo, lyxo, arabino, and ribo imidazolo-pentoses in both the L- and the D-series, intramolecular Walden inversion led to the corresponding arabino, ribo, xylo, and lyxo pyrrolidinopentoses in the D- and the L-series, respectively, protection and deprotection steps being unavoidable prerequisites. The structures and configurations of all eight pyrrolidinopentoses were determined unambiguously, by a combination of 1H/13C NMR spectroscopy, circular dichroism and [alpha](D) values, in conjunction with single-crystal X-ray diffraction analysis of the L-xylo stereoisomer. Examination of the inhibitory properties of these imidazolo-pyrrolidinoses against six commonly encountered glycosidases led to the conclusion that by and large the L-stereoisomers are inactive, whereas three out the four D-stereoisomers proved to be poor to moderate inhibitors. It appears therefore that the most basic N(1) atom is not located in an optimal topology to be protonated easily inside the enzyme's active site.

journal_name

Bioorg Med Chem

journal_title

Bioorganic & medicinal chemistry

authors

Tschamber T,Gessier F,Dubost E,Newsome J,Tarnus C,Kohler J,Neuburger M,Streith J

doi

10.1016/s0968-0896(03)00402-4

subject

Has Abstract

pub_date

2003-08-15 00:00:00

pages

3559-68

issue

17

eissn

0968-0896

issn

1464-3391

pii

S0968089603004024

journal_volume

11

pub_type

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