分枝杆菌中含海藻糖的脂寡糖：寡糖片段的结构以及一种独特的含N-酰基卡那胺表位的识别

Trehalose-containing lipooligosaccharides from mycobacteria: structures of the oligosaccharide segments and recognition of a unique N-acylkanosamine-containing epitope.

作者信息

Hunter S W, Jardine I, Yanagihara D L, Brennan P J

出版信息

Biochemistry. 1985 May 21;24(11):2798-805. doi: 10.1021/bi00332a030.

Abstract

The structures of the oligosaccharide segments of nine trehalose-containing lipooligosaccharides (LOS) of Mycobacterium kansasii have been established by positive and negative fast-atom bombardment mass spectrometry, acetolysis, partial acid hydrolysis, methylation analyses, and nuclear magnetic resonance. Upon acetolysis, all produce the alpha,alpha-trehalose-containing tetraglucose (Glc4) "core" -beta-D-Glcp(1----3)-beta-D-Glcp(1----4)-alpha-D-Glcp(1----1)-alpha-D-Gl cp. The simplest (LOS I') contains an additional alpha 1----3-linked 3-O-methyl-L-rhamnopyranose (3-O-Me-L-Rhap) unit; those of intermediate complexity (LOS I-III) contain an additional D-xylopyranose (D-Xylp) residue or xylobiose in beta 1----4 linkage; and those of ultimate complexity (LOS IV-VIII) contain further D-Xylp residues and the distal N-acylkanosamine- (KanNAcyl) and fucopyranosyl- (Fucp) containing disaccharide KanNAcyl(1----3)Fucp. Thus, the structure of the oligosaccharide from LOS VII is KanNAcyl(1----3)Fucp(1----4) [-beta-D-Xylp(1----4)]6-alpha-L-3-O-Me-Rhap(1----3)Glc4++ +. Polyclonal rabbit and murine monoclonal antibodies react only with the more complex KanNAcyl-Fucp-containing lipooligosaccharides, indicating that the KanNAcyl distal end, not the trehalose end, contains the antibody binding site unique to M. kansasii and is responsible for the serological distinctiveness of M. kansasii among mycobacterial species.

摘要

堪萨斯分枝杆菌的9种含海藻糖脂寡糖（LOS）的寡糖片段结构已通过正、负离子快原子轰击质谱、乙酰解、部分酸水解、甲基化分析和核磁共振得以确定。乙酰解后，所有产物均生成含α,α-海藻糖的四葡萄糖（Glc4）“核心”——β-D-葡萄糖吡喃糖基(1→3)-β-D-葡萄糖吡喃糖基(1→4)-α-D-葡萄糖吡喃糖基(1→1)-α-D-葡萄糖吡喃糖。最简单的（LOS I'）含有一个额外的α1→3连接的3-O-甲基-L-鼠李糖吡喃糖（3-O-Me-L-Rhap）单元；中等复杂程度的（LOS I-III）含有一个额外的D-木糖吡喃糖（D-Xylp）残基或β1→4连接的木二糖；而最复杂的（LOS IV-VIII）则含有更多的D-Xylp残基以及远端含N-酰基卡那胺-（KanNAcyl）和岩藻糖吡喃糖基-（Fucp）的二糖KanNAcyl(1→3)Fucp。因此，LOS VII的寡糖结构为KanNAcyl(1→3)Fucp(1→4)[-β-D-Xylp(1→4)]6-α-L-3-O-Me-Rhap(1→3)Glc4+++。兔多克隆抗体和鼠单克隆抗体仅与更复杂的含KanNAcyl-Fucp脂寡糖发生反应，这表明KanNAcyl远端而非海藻糖末端含有堪萨斯分枝杆菌特有的抗体结合位点，并且是堪萨斯分枝杆菌在分枝杆菌物种中血清学独特性的原因。