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Synthesis of Glucopyranoside-Based Ligands for D-myo-inositol 1,4,5-trisphosphate Receptors

Synthesis of Glucopyranoside-Based Ligands for D-myo-inositol 1,4,5-trisphosphate Receptors

Andrew M Riley, David J Jenkins, Rachel D Marwood, Barry V L Potter

Carbohydr Res. 2002 Jun 12;337(12):1067-82.

PMID: 12062522

Abstract:

Adenophostins A and B are naturally occurring glyconucleotides that interact potently with receptors for D-myo-inositol 1,4,5-trisphosphate, an important second messenger molecule in most cell types. Here we describe the design and synthesis of glucopyranoside-based analogues of adenophostin A lacking the adenine component. The key synthetic strategy involves glycosylation of selectively protected alcohols, derived from methyl beta-D-ribofuranoside or 1,4-anhydroerythritol, using glycosyl donors synthesised from 2,6-di-O-benzyl-D-glucopyranose derivatives. Further elaboration and deprotection of the coupled products gave two trisphosphate analogues; methyl 3-O-alpha-D-glucopyranosyl-beta-D-ribofuranoside 2,3',4'-trisphosphate ("ribophostin") and (3'S,4'R)-3'-hydroxytetrahydrofuran-4'-yl alpha-D-glucopyranoside 3,4,3'-trisphosphosphate ("furanophostin"). The route to furanophostin was further modified to give (3'S,4'R)-3'-hydroxytetrahydrofuran-4'-yl alpha-D-glucopyranoside 3'-phosphate 3,4-bisphosphorothioate, the first phosphorothioate-containing adenophostin analogue.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP86087232	(S)-(+)-3-Hydroxytetrahydrofuran		86087-23-2	Price

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