Arabinofuranosides from mycobacteria:: Synthesis of a highly branched hexasaccharide and related fragments containing β-axabinofuranosyl residues

被引:89
作者
Yin, HF [1 ]
D'Souza, FW [1 ]
Lowary, TL [1 ]
机构
[1] Ohio State Univ, Dept Chem, Columbus, OH 43210 USA
关键词
D O I
10.1021/jo010910e
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis of 11 oligosaccharides (4-14) containing beta-arabinofuranosyl residues is reported. The glycans are all fragments of two polysaccharides, arabinogalactan and lipoarabinomannan, which are found in the cell wall complex of mycobacteria. In the preparation of the targets, the key step was a low-temperature glycosylation reaction that installed the P-arabinofuranosyl residues with good to excellent stereocontrol.
引用
收藏
页码:892 / 903
页数:12
相关论文
共 54 条
[1]   Synthetic arabinofuranosyl oligosaccharides as mycobacterial arabinosyltransferase substrates [J].
Ayers, JD ;
Lowary, TL ;
Morehouse, CB ;
Besra, GS .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1998, 8 (05) :437-442
[2]  
BARRESI F, 1996, FRONT NAT PROD RES, V1, P251
[3]   New horizons in the treatment of tuberculosis [J].
Barry, CE .
BIOCHEMICAL PHARMACOLOGY, 1997, 54 (11) :1165-1172
[4]   Use of genomics and combinatorial chemistry in the development of new antimycobacterial drugs [J].
Barry, CE ;
Slayden, RA ;
Sampson, AE ;
Lee, RE .
BIOCHEMICAL PHARMACOLOGY, 2000, 59 (03) :221-231
[5]   A NEW INTERPRETATION OF THE STRUCTURE OF THE MYCOLYL ARABINOGALACTAN COMPLEX OF MYCOBACTERIUM-TUBERCULOSIS AS REVEALED THROUGH CHARACTERIZATION OF OLIGOGLYCOSYLALDITOL FRAGMENTS BY FAST-ATOM-BOMBARDMENT MASS-SPECTROMETRY AND H-1 NUCLEAR-MAGNETIC-RESONANCE SPECTROSCOPY [J].
BESRA, GS ;
KHOO, KH ;
MCNEIL, MR ;
DELL, A ;
MORRIS, HR ;
BRENNAN, PJ .
BIOCHEMISTRY, 1995, 34 (13) :4257-4266
[6]   TUBERCULOSIS - COMMENTARY ON A REEMERGENT KILLER [J].
BLOOM, BR ;
MURRAY, CJL .
SCIENCE, 1992, 257 (5073) :1055-1064
[7]   Stereoselective synthesis of arabinose-derived phosphonates [J].
Bouix, C ;
Bisseret, P ;
Eustache, J .
TETRAHEDRON LETTERS, 1998, 39 (08) :825-828
[8]   THE ENVELOPE OF MYCOBACTERIA [J].
BRENNAN, PJ ;
NIKAIDO, H .
ANNUAL REVIEW OF BIOCHEMISTRY, 1995, 64 :29-63
[9]  
CHATTERJEE D, 1991, J BIOL CHEM, V266, P9652
[10]   STRUCTURAL BASIS OF CAPACITY OF LIPOARABINOMANNAN TO INDUCE SECRETION OF TUMOR-NECROSIS-FACTOR [J].
CHATTERJEE, D ;
ROBERTS, AD ;
LOWELL, K ;
BRENNAN, PJ ;
ORME, IM .
INFECTION AND IMMUNITY, 1992, 60 (03) :1249-1253