Imino-sugar-based nucleosides

被引:50
作者
Schramm, VL
Tyler, PC
机构
[1] Ind Res Ltd, Carbohydrate Chem, Lower Hutt, New Zealand
[2] Yeshiva Univ Albert Einstein Coll Med, Dept Biochem, Bronx, NY 10461 USA
关键词
D O I
10.2174/1568026033452465
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Continued interest in imino-sugar nucleosides derives from the observations that N-ribosyltransferases are powerfully inhibited by imino-C-nucleoside analogues that mimic the ribooxacarbenium ion nature of their transition states. The synthesis of such compounds is challenging, and synthetic routes to imino- and imino-C-nucleosides are reviewed, together with the nature of the N-ribosyltransferases that are targets for these analogues. Examples are given to exemplify the promise these compounds hold for the treatments of biological disorders.
引用
收藏
页码:525 / 540
页数:16
相关论文
共 81 条
[11]   Trypanosomal nucleoside hydrolase. A novel mechanism from the structure with a transition-state inhibitor [J].
Degano, M ;
Almo, SC ;
Sacchettini, JC ;
Schramm, VL .
BIOCHEMISTRY, 1998, 37 (18) :6277-6285
[12]   Trypanosomal nucleoside hydrolase. Resonance Raman spectroscopy of a transition-state inhibitor complex [J].
Deng, H ;
Chan, AWY ;
Bagdassarian, CK ;
Estupinan, B ;
Ganem, B ;
Callender, RH ;
Schramm, VL .
BIOCHEMISTRY, 1996, 35 (19) :6037-6047
[13]   Unusually strong binding of a designed transition-state analog to a base-excision DNA repair protein [J].
Deng, L ;
Scharer, OD ;
Verdine, GL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (33) :7865-7866
[14]  
ESTUPINAN B, 1994, J BIOL CHEM, V269, P23068
[15]   Addition of lithiated 9-deazapurine derivatives to a carbohydrate cyclic imine:: Convergent synthesis of the aza-C-nucleoside immucillins [J].
Evans, GB ;
Furneaux, RH ;
Hutchison, TL ;
Kezar, HS ;
Morris, PE ;
Schramm, VL ;
Tyler, PC .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (17) :5723-5730
[16]   Synthesis of transition state analogue inhibitors for purine nucleoside phosphorylase and N-riboside hydrolases [J].
Evans, GB ;
Furneaux, RH ;
Gainsford, GJ ;
Schramm, VL ;
Tyler, PC .
TETRAHEDRON, 2000, 56 (19) :3053-3062
[18]   Improved syntheses of 3H,5H-pyrrolo[3,2-d]pyrimidines [J].
Furneaux, RH ;
Tyler, PC .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (22) :8411-8412
[19]   Synthesis of transition state inhibitors for N-riboside hydrolases and transferases [J].
Furneaux, RH ;
Limberg, G ;
Tyler, PC ;
Schramm, VL .
TETRAHEDRON, 1997, 53 (08) :2915-2930
[20]   Transition state analogue inhibitors of protozoan nucleoside hydrolases [J].
Furneaux, RH ;
Schramm, VL ;
Tyler, PC .
BIOORGANIC & MEDICINAL CHEMISTRY, 1999, 7 (11) :2599-2606