Cystic fibrosis and diabetes: isoLAB and isoDAB, enantiomeric carbon-branched pyrrolidine iminosugars

被引：44

作者：

Best, Daniel ^{[1
]}

Jenkinson, Sarah F. ^{[1
]}

Saville, A. Waldo ^{[1
]}

Alonzi, Dominic S. ^{[3
]}

Wormald, Mark R. ^{[3
]}

Butters, Terry D. ^{[3
]}

Norez, Caroline ^{[4
]}

Becq, Frederic ^{[4
]}

Bleriot, Yves ^{[5
]}

Adachi, Isao ^{[2
]}

Kato, Atsushi ^{[2
]}

Fleet, George W. J. ^{[1
]}

机构：

[1] Univ Oxford, Dept Chem, Chem Res Lab, Oxford OX1 3TA, England

[2] Toyama Univ, Dept Hosp Pharm, Toyama 9300194, Japan

[3] Univ Oxford, Oxford Glycobiol Inst, Oxford OX1 3QU, England

[4] Univ Poitiers, CNRS, Inst Physiol & Biol Cellulaires, F-86022 Poitiers, France

[5] Lab Synth & React Subst Nat, UMR 6514, F-86022 Poitiers, France

来源：

TETRAHEDRON LETTERS | 2010年 / 51卷 / 32期

关键词：

LOOKING-GLASS INHIBITORS; GLYCOSIDASE INHIBITORS; PHARMACOLOGICAL RESCUE; GLUCOSIDASE INHIBITOR; EPITHELIAL-CELLS; POTENT INHIBITOR; ANGYLOCALYX-BOUTIQUEANUS; GLYCOGEN-PHOSPHORYLASE; ARACHNIODES-STANDISHII; ALPHA-GLUCOSIDASES;

D O I：

10.1016/j.tetlet.2010.05.131

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Acetonides are the only protecting groups used in the syntheses of isoDAB from D-ribose and of isoLAB from D-tagatose. isoDAB is a potent and highly specific competitive a-glucosidase inhibitor (for rice alpha-glucosidase, K(i) = 4 mu M for isoDAB compared to K(i) 14 mu M for DAB). isoDAB is not an whereas DAB is a potent inhibitor of glycogen phosphorylase. This is the first example of any potent inhibition of glycosidases by a carbon-branched iminosugar pyrrolidine. Although isoLAB shows no inhibition of any glycosidase, preliminary experiments suggest that isoLAB partially rescues the defective F508del-CFTR function and so may have a role in the study of cystic fibrosis. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：4170 / 4174

页数：5

共 71 条

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