Synthesis and biological evaluation of new inhibitors of UDP-Galf transferase -: a key enzyme in M-tuberculosis cell wall biosynthesis

被引：57
作者：
Cren, S
Gurcha, SS
Blake, AJ
Besra, GS
Thomas, NR
机构：
[1] Univ Nottingham, Ctr Biomol Sci, Sch Chem, Nottingham NG7 2RD, England
[2] Univ Birmingham, Sch Biosci, Birmingham B15 2TT, W Midlands, England
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2004年 / 2卷 / 17期
关键词：
D O I：
10.1039/B411554f
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Two iminosugars have been designed and synthesized as potential inhibitors of UDP-Galf transferase, an enzyme involved in Mycobacterium tuberculosis cell wall biosynthesis. The design is based on a proposed model of the transition state for the transferase reaction. One of the two racemic compounds is the first reported inhibitor of the target enzyme from M. smegmatis.
引用
收藏
页码：2418 / 2420
页数：3
相关论文
共 24 条
[1]   Positional isotope exchange catalyzed by UDP-galactopyranose mutase [J].
Barlow, JN ;
Girvin, ME ;
Blanchard, JS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (29) :6968-6969
[2]   Efficient synthesis of a nucleoside-diphospho-exo-glycal displaying time-dependent inactivation of UDP-galactopyranose mutase [J].
Caravano, A ;
Vincent, SP ;
Sinay, P .
CHEMICAL COMMUNICATIONS, 2004, (10) :1216-1217
[3]   Synthesis and inhibition properties of conformational probes for the mutase-catalyzed UDP-galactopyranose/furanose interconversion [J].
Caravano, A ;
Mengin-Lecreulx, D ;
Brondello, JM ;
Vincent, SP ;
Sinaÿ, P .
CHEMISTRY-A EUROPEAN JOURNAL, 2003, 9 (23) :5888-5898
[4]   Carbohydrate mimetics-based glycosyltransferase inhibitors [J].
Compain, P ;
Martin, OR .
BIOORGANIC & MEDICINAL CHEMISTRY, 2001, 9 (12) :3077-3092
[5]  
DAFFE M, 1990, J BIOL CHEM, V265, P6734
[6]   Synthesis of an aza analogue of 2-deoxy-D-ribofuranose and its homologues [J].
Filichev, VV ;
Brandt, M ;
Pedersen, EB .
CARBOHYDRATE RESEARCH, 2001, 333 (02) :115-122
[7]   Intercalating nucleic acids (INAs) with insertion of N-(pyren-1-ylmethyl)-(3R,4R)-4-(hydroxymethyl)pyrrolidin-3-ol.: DNA (RNA) duplex and DNA three-way junction stabilities [J].
Filichev, VV ;
Pedersen, EB .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2003, 1 (01) :100-103
[8]   Potentiometric analysis of UDP-galactopyranose mutase: Stabilization of the flavosemiquinone by substrate [J].
Fullerton, SWB ;
Daff, S ;
Sanders, DAR ;
Ingledew, WJ ;
Whitfield, C ;
Chapman, SK ;
Naismith, JH .
BIOCHEMISTRY, 2003, 42 (07) :2104-2109
[9]  
Halfman C J, 1981, Methods Enzymol, V74 Pt C, P481
[10]   1-azaribofuranoside analogues as designed inhibitors of purine nucleoside phosphorylase. Synthesis and biological evaluation [J].
Hansen, SU ;
Bols, M .
ACTA CHEMICA SCANDINAVICA, 1998, 52 (10) :1214-1222
123