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Synthesis of the (1→6)-linked thiodisaccharide of galactofuranose: inhibitory activity against a β-galactofuranosidase.

Abstract：

:A new (1→6)-linked thiodisaccharide formed by two galactofuranosyl units has been synthesized. Methyl (methyl α,β-D-galactofuranosid)uronate was employed as the starting compound, which was per-O-silylated with TBSCl and reduced with LiAlH4 to afford methyl 2,3,5-tri-O-tert-butyldimethylsilyl-β-D-galactofuranoside (2β) as a key precursor for the preparation of methyl per-O-tert-butyldimethylsilyl-6-thio-β-D-galactofuranoside (12). The free thiol group of 12 was glycosylated and the product O-deprotected to afford the target β-D-Galf-S-(1→6)-β-d-Galf-OMe (14). The conformations of this thiodisaccharide were preliminarily studied using combined theoretical calculations and NMR data. Furthermore, the glycomimetic 14 showed to be a competitive inhibitor of the β-galactofuranosidase from Penicillum fellutanum (K(i)=3.62 mM).

journal_name

Bioorg Med Chem

journal_title

Bioorganic & medicinal chemistry

authors

Repetto E,Marino C,Varela O

doi

10.1016/j.bmc.2013.02.057

subject

Has Abstract

pub_date

2013-06-01 00:00:00

pages

3327-33

issue

11

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(13)00255-1

journal_volume

21

pub_type

杂志文章

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