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

来源：

TETRAHEDRON-ASYMMETRY | 2004年 / 15卷 / 02期

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

页码：189 / 193

页数：5

共 31 条

[11]

Gravier-Pelletier C, 2001, EUR J ORG CHEM, V2001, P3089

[12]

HENRY CM, 2000, C EN WASHINGTON, V41

[13] CURRENT PROGRESS ON NUCLEOSIDE ANTIBIOTICS [J].

ISONO, K .

PHARMACOLOGY & THERAPEUTICS, 1991, 52 (03) :269-286

[14] LIPOSIDOMYCINS - NOVEL NUCLEOSIDE ANTIBIOTICS WHICH INHIBIT BACTERIAL PEPTIDOGLYCAN SYNTHESIS [J].

ISONO, K ;

URAMOTO, M ;

KUSAKABE, H ;

KIMURA, KI ;

IZAKI, K ;

NELSON, CC ;

MCCLOSKEY, JA .

JOURNAL OF ANTIBIOTICS, 1985, 38 (11) :1617-1621

[15] LIPOSIDOMYCIN-C INHIBITS PHOSPHO-N-ACETYLMURAMYL-PENTAPEPTIDE TRANSFERASE IN PEPTIDOGLYCAN SYNTHESIS OF ESCHERICHIA-COLI Y-10 [J].

KIMURA, K ;

MIYATA, N ;

KAWANISHI, G ;

KAMIO, Y ;

IZAKI, K ;

ISONO, K .

AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1989, 53 (07) :1811-1815

[16] Access to enantiopure ribosyl-diazepanone core of liposidomycins [J].

Le Merrer, Y ;

Gravier-Pelletier, C ;

Gerrouache, M ;

Depezay, JC .

TETRAHEDRON LETTERS, 1998, 39 (5-6) :385-388

[17] The challenge of antibiotic resistance [J].

Levy, SB .

SCIENTIFIC AMERICAN, 1998, 278 (03) :46-53

[18] Synthesis of sialyl Lewis X mimetics and related structures using the glycosyl phosphite methodology and evaluation of E-selectin inhibition [J].

Lin, CC ;

Shimazaki, M ;

Heck, MP ;

Aoki, S ;

Wang, R ;

Kimura, T ;

Ritzen, H ;

Takayama, S ;

Wu, SH ;

WeitzSchmidt, G ;

Wong, CH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (29) :6826-6840

[19] Preparation of glycosylated amino acid derivatives for glycoprotein synthesis by in vitro translation system [J].

Manabe, S ;

Sakamoto, K ;

Nakahara, Y ;

Sisido, M ;

Hohsaka, T ;

Ito, Y .

BIOORGANIC & MEDICINAL CHEMISTRY, 2002, 10 (03) :573-581

[20] AN EFFICIENT METHOD FOR GLUCOSYLATION OF HYDROXY COMPOUNDS USING GLUCOPYRANOSYL FLUORIDE [J].

MUKAIYAMA, T ;

MURAI, Y ;

SHODA, S .

CHEMISTRY LETTERS, 1981, (03) :431-432

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