Synthesis of 2-acetamido-1,2-dideoxy-D-galacto-nojirimycin [DGJNAc] from D-glucuronolactone: the first sub-micromolar inhibitor of α-N-acetylgalactosaminidases

被引：25

作者：

Best, Daniel ^{[1
]}

Chairatana, Phoom ^{[1
]}

Glawar, Andreas F. G. ^{[1
,2
]}

Crabtree, Elizabeth ^{[1
,2
]}

Butters, Terry D. ^{[2
]}

Wilson, Francis X. ^{[5
]}

Yu, Chu-Yi ^{[4
]}

Wang, Wu-Bao ^{[4
]}

Jia, Yue-Mei ^{[4
]}

Adachi, Isao ^{[3
]}

Kato, Atsushi ^{[3
]}

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

机构：

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

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

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

[4] Chinese Acad Sci, Inst Chem, CAS Key Lab Mol Recognit & Funct, Beijing 100190, Peoples R China

[5] Summit PLC, Abingdon OX14 4RY, Oxon, England

来源：

TETRAHEDRON LETTERS | 2010年 / 51卷 / 17期

关键词：

BETA-HEXOSAMINIDASE INHIBITOR; 2S; 3R; 4R; 5S-TRIHYDROXYPIPECOLIC ACID; 2R; 4S; 5S-DIHYDROXYPIPECOLIC ACID; 1-DEOXYNOJIRIMYCIN SYSTEM; ENANTIOSPECIFIC SYNTHESES; GLYCOSIDASE INHIBITORS; EFFICIENT SYNTHESIS; NATURAL OCCURRENCE; L-ENANTIOMERS;

D O I：

10.1016/j.tetlet.2010.02.063

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

2-Acetamido-1,2-dideoxy-D-galacto-nojirimycin [DGJNAc], prepared in 20% overall yield from D-glucuronolactone, is the first potent competitive sub-micromolar inhibitor of alpha-N-acetyl-galactosaminidases (K-i 0.081 mu M from chicken liver, K-i 0.136 mu M from Charonia lampas). DGJNAc is a good competitive-whereas the enantiomer L-DGJNAc is a very weak but non-competitive inhibitor of beta-hexosaminidases. (C) 2010 Published by Elsevier Ltd.

引用

页码：2222 / 2224

页数：3

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