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Xylopyranoside-based Agonists of D-myo-inositol 1,4,5-trisphosphate Receptors: Synthesis and Effect of Stereochemistry on Biological Activity

Xylopyranoside-based Agonists of D-myo-inositol 1,4,5-trisphosphate Receptors: Synthesis and Effect of Stereochemistry on Biological Activity

H J Rosenberg, A M Riley, R D Marwood, V Correa, C W Taylor, Potter BVL

Carbohydr Res. 2001 May 8;332(1):53-66.

PMID: 11403088

Abstract:

The synthesis of a series of tetrahydrofuranyl alpha- and beta-xylopyranoside trisphosphates, designed by excision of three motifs of adenophostin A is reported. The synthetic route features improved preparations of allyl alpha-D-xylopyranoside and its 2-O-benzyl ether, and gives access to four diastereoisomeric trisphosphates, which show a range of abilities to mobilise Ca2+ from the intracellular stores of hepatocytes. A comparison of the potencies of the four trisphosphates provides useful information relating to the effects of stereochemical variation on the recognition of carbohydrate-based trisphosphates by D-myo-inositol 1,4,5-trisphosphate receptors. 1-O-[(3'S,4'R)-3-hydroxytetrahydrofuran-4-yl] alpha-D-xylopyranoside 3,4,3'-trisphosphate (8) is the most active member of the series with a potency close to Ins(1,4,5)P3; a beta-linked analogue, 1-O-[(3'R,4'S)-3-hydroxytetrahydrofuran-4-yl] beta-D-xylopyranoside 3,4,3'-trisphosphate, is ca. 20-fold weaker than Ins(1,4,5)P3, and the other compounds are much less active. While no compound attained a potency close to that of adenophostin A, we believe that 8 represents the minimal structure for potent Ca2+-releasing activity in this type of carbohydrate-based 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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