A versatile scaffold for a library of liposidomycins analogues: A crucial and potent glycosylation step

被引:15
作者
Gravier-Pelletier, C [1 ]
Ginisty, M [1 ]
Le Merrer, Y [1 ]
机构
[1] Univ Paris 05, UMR 8601 CNRS, Lab Chim & Biochim Pharmacol & Toxicol, F-75270 Paris 06, France
关键词
D O I
10.1016/j.tetasy.2003.10.017
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
A key step for the synthesis of a diazepanone scaffold dedicated to a library of MraY inhibitors is described. It involves the O-glycosylation of a conveniently protected L-serine by a D-ribofuranose derivative. High yield and selectivity were obtained. (C) 2003 Elsevier Ltd. All rights reserved.
引用
收藏
页码:189 / 193
页数:5
相关论文
共 31 条
[1]   SYNTHESIS OF RIBONUCLEOSIDES OF 4(5)-CYANO-5(4)-METHYLIMIDAZOLE AND RELATED 4-SUBSTITUTED-5-METHYLIMIDAZOLE RIBOSIDES [J].
ANDRES, JI ;
GARCIALOPEZ, MT .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1986, 23 (03) :679-683
[2]   Topological analysis of the MraY protein catalysing the first membrane step of peptidoglycan synthesis [J].
Bouhss, A ;
Mengin-Lecreulx, D ;
Le Beller, D ;
van Heijenoort, J .
MOLECULAR MICROBIOLOGY, 1999, 34 (03) :576-585
[3]   2-BROMOETHYL GLYCOSIDES - SYNTHESIS AND CHARACTERIZATION [J].
DAHMEN, J ;
FREJD, T ;
GRONBERG, G ;
LAVE, T ;
MAGNUSSON, G ;
NOORI, G .
CARBOHYDRATE RESEARCH, 1983, 116 (02) :303-307
[4]   INACTIVATION OF ANTIBIOTICS AND THE DISSEMINATION OF RESISTANCE GENES [J].
DAVIES, J .
SCIENCE, 1994, 264 (5157) :375-382
[5]   Medicine - Bacteria on the rampage [J].
Davies, J .
NATURE, 1996, 383 (6597) :219-220
[6]   Synthesis and biological evaluation of cyclophostin:: A 5′,6"-tethered analog of adenophostin A [J].
de Kort, M ;
Regenbogen, AD ;
Overkleeft, HS ;
Challiss, RAJ ;
Iwata, Y ;
Miyamoto, S ;
van der Marel, GA ;
van Boom, JH .
TETRAHEDRON, 2000, 56 (32) :5915-5928
[7]   Stereoselective chemical 1,2-cis O-glycosylation:: From 'sugar ray' to modern techniques of the 21st century [J].
Demchenko, AV .
SYNLETT, 2003, (09) :1225-1240
[8]   Synthesis of analogues of the O-β-D-ribofuranosyl nucleoside moiety of liposidomycins.: part 2:: Role of the hydroxyl groups upon the inhibition of MraY [J].
Dini, C ;
Drochon, N ;
Guillot, JC ;
Mauvais, P ;
Walter, P ;
Aszodi, J .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2001, 11 (04) :533-536
[9]   Synthesis of analogues of the O-β-D-ribofuranosyl nucleoside moiety of liposidomycins.: part 1:: Contribution of the amino group and the uracil moiety upon the inhibition of MraY [J].
Dini, C ;
Drochon, N ;
Feteanu, S ;
Guillot, JC ;
Peixoto, C ;
Aszodi, J .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2001, 11 (04) :529-531
[10]   Synthesis of the nucleoside moiety of liposidomycins: Elucidation of the pharmacophore of this family of MraY inhibitors [J].
Dini, C ;
Collette, P ;
Drochon, N ;
Guillot, JC ;
Lemoine, G ;
Mauvais, P ;
Aszodi, J .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2000, 10 (16) :1839-1843