TETRAZOLES OF MANNO-PYRANOSES AND RHAMNO-PYRANOSES - INHIBITION OF GLYCOSIDASES BY TETRAZOLES AND OTHER MANNOSE MIMICS

被引:34
作者
BRANDSTETTER, TW
DAVIS, B
HYETT, D
SMITH, C
HACKETT, L
WINCHESTER, BG
FLEET, GWJ
机构
[1] OXFORD CTR MOLEC SCI,DYSON PERRINS LAB,OXFORD OX1 3QY,ENGLAND
[2] GLAXO WELLCOME MED RES CTR,STEVENAGE SG1 2NY,HERTS,ENGLAND
[3] UNIV LONDON,INST CHILD HLTH,LONDON WC1 1EH,ENGLAND
[4] UNIV LONDON,GREAT ORMOND ST HOSP CHILDREN,NHS TRUST,LONDON WC1 1EH,ENGLAND
关键词
D O I
10.1016/0040-4039(95)01519-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis of tetrazoles derived from D-mannopyranose and D-rhamnopyranose from L-gulonolactone is described. These and other materials are assessed as inhibitors of human liver glycosidases and delineate some structural features required for alpha- and beta-mannosidase and alpha-fucosidase inhibition.
引用
收藏
页码:7511 / 7514
页数:4
相关论文
共 38 条
[1]  
AHRENS PB, 1993, J BIOL CHEM, V268, P385
[2]   ENHANCEMENT OF PHORBOL ESTER-INDUCED CELL-AGGREGATION AFTER ALTERATIONS IN ASPARAGINE-LINKED OLIGOSACCHARIDES [J].
AHRENS, PB .
BIOLOGY OF THE CELL, 1993, 77 (03) :255-260
[3]   NAGSTATIN, A NEW INHIBITOR OF N-ACETYL-BETA-D-GLUCOSAMINIDASE, PRODUCED BY STREPTOMYCES-AMAKUSAENSIS MG846-FF3 - TAXONOMY, PRODUCTION, ISOLATION, PHYSICOCHEMICAL PROPERTIES AND BIOLOGICAL-ACTIVITIES [J].
AOYAGI, T ;
SUDA, H ;
UOTANI, K ;
KOJIMA, F ;
AOYAMA, T ;
HORIGUCHI, K ;
HAMADA, M ;
TAKEUCHI, T .
JOURNAL OF ANTIBIOTICS, 1992, 45 (09) :1404-1408
[4]   THE STRUCTURE OF NAGSTATIN, A NEW INHIBITOR OF N-ACETYL-BETA-D-GLUCOSAMINIDASE [J].
AOYAMA, T ;
NAGANAWA, H ;
SUDA, H ;
UOTANI, K ;
AOYAGI, T ;
TAKEUCHI, T .
JOURNAL OF ANTIBIOTICS, 1992, 45 (09) :1557-1558
[5]   NITROGEN-IN-THE-RING PYRANOSES AND FURANOSES - STRUCTURAL BASIS OF INHIBITION OF MAMMALIAN GLYCOSIDASES [J].
ASANO, N ;
OSEKI, K ;
KIZU, H ;
MATSUI, K .
JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (22) :3701-3706
[6]  
ASANO N, 1995, IN PRESS J MED CHEM, V38
[7]   SYNTHESIS OF THE MANNOSIDASE INHIBITORS SWAINSONINE AND 1,4-DIDEOXY-1,4-IMINO-D-MANNITOL AND OF THE RING CONTRACTED SWAINSONINES, (1S, 2R, 7R, 7AR)-1,2,7-TRIHYDROXYPYRROLIZIDINE AND (1S, 2R, 7S, 7AR)-1,2,7-TRIHYDROXYPYRROLIZIDINE [J].
CARPENTER, NM ;
FLEET, GWJ ;
DIBELLO, IC ;
WINCHESTER, B ;
FELLOWS, LE ;
NASH, RJ .
TETRAHEDRON LETTERS, 1989, 30 (51) :7261-7264
[8]  
CHANDRASEKARAN S, 1994, J BIOL CHEM, V269, P3356
[9]   EFFECTS OF THE ALPHA-MANNOSIDASE INHIBITORS, 1,4-DIDEOXY-1,4-IMINO-D-MANNITOL AND SWAINSONINE, ON GLYCOPROTEIN CATABOLISM IN CULTURED MACROPHAGES [J].
DANIEL, PF ;
NEWBURG, DS ;
ONEIL, NE ;
SMITH, PW ;
FLEET, GWJ .
GLYCOCONJUGATE JOURNAL, 1989, 6 (02) :229-240
[10]   TETRAZOLES OF MANNO-FURANOSES AND RHAMNO-FURANOSES [J].
DAVIS, B ;
BRANDSTETTER, TW ;
SMITH, C ;
HACKETT, L ;
WINCHESTER, BG ;
FLEET, GWJ .
TETRAHEDRON LETTERS, 1995, 36 (41) :7507-7510