Structure of a novel glycopeptidolipid antigen containing a O-methylated serine isolated from Mycobacterium xenopi. Complete 1H-NMR and 13C-NMR assignment.
Structure of a novel glycopeptidolipid antigen containing a O-methylated serine isolated from Mycobacterium xenopi. Complete 1H-NMR and 13C-NMR assignment.
复制标题
含有从蟾蜍分枝杆菌中分离出的 O-甲基化丝氨酸的新型糖肽脂抗原的结构。
DOI：
10.1111/j.1432-1033.1993.tb17935.x
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发表时间：
1993
期刊：
影响因子：
--
通讯作者：
G. Puzo
中科院分区：
文献类型：
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作者：
M. Rivière;S. Augé;J. Vercauteren;E. Wisingerová;G. Puzo
GPL X-1是一种从xenopi分枝杆菌（CIPT 140 35004）中分离出来的新型糖肽类脂（GPL X-1），最近被发现代表了一类新的分枝杆菌糖肽类脂缺乏c -真菌苷核心结构，即所谓的含丝氨酸糖肽类脂[rivi<e:1>， M. & Puzo， G. (1991) J. Biol.]。化学，26(6),9057-9063。在这里，我们报道了一种新的含丝氨酸的GPL的纯化和鉴定，称为GPL X-IIb，分离自非洲芽孢杆菌菌株NCTC 10042。在薄层色谱上，这种GPL被发现存在于从肺部感染患者分离的其他一些非洲分枝杆菌菌株中。利用二维同核和异核标量耦合核磁共振从天然形式对该GPL的糖和氨基酸组成进行了鉴定。多肽和糖的序列，以及甲氧基在6-脱氧- l -塔罗吡喃苷（6dTalp）的C-3和丝氨酸上的位置，通过异核多键相关实验明确地确定了。发现GPL X-IIb由以下结构的脂四肽c12 - ser - ome - ser - ph -aThr- ome （aThr = allo苏氨酸）组成。糖部分由3ome - α - l - 6dtalp和以下双糖组成：α - l -Rhap-(1—>3)-2- o - law - α - l -Rhap （Rhap = rhanmopyranose）。与GPL X-I不同的是，在aThr-OMe和Ser的异核多键相关谱中观察到的异核碳共振与β质子之间的异核三键耦合相关中，成功地确定了四肽上的糖附着位点。结果表明，3OMe-6dTalp糖基化了丝氨酸，而双糖与aThr-OMe连接。因此，GPL X-I和GPL X-IIb都有一个共同的脂四肽核心[Ser（OMe）除外]，但它们的低聚糖附属物截然不同。因此，与M. avium复合体类似，本报告表明，由于其C-mycoside GPL寡糖附属物的独特结构，xenopi物种可以分为不同的血清型，从而增强了对这种新型含丝氨酸的糖肽类脂的兴趣。
GPL X-1, a novel glycopeptidolipid (GPL) isolated from Mycobacterium xenopi (CIPT 140 35004), has recently been found to typify a new class of mycobacterial glycopeptidolipids devoid of C-mycoside core structure, the so-called serine-containing glycopeptidolipid [Rivière, M. & Puzo, G. (1991) J. Biol. Chem. 266, 9057-9063]. Here we report the purification and characterization of a novel serine-containing GPL termed GPL X-IIb, isolated from the M. xenopi strain NCTC 10042. On thin-layer chromatography, this GPL was found to be present in some other M. xenopi strains isolated from patients with pulmonary infections. The sugar and amino-acid compositions of this GPL were elucidated from the native form using a combination of two-dimensional homonuclear and heteronuclear scalar coupling NMR. The peptide and sugar sequences, as well as the methoxyl group locations on the C-3 of the 6-deoxy-alpha-L-talopyranoside (6dTalp) and on a Ser, were unambiguously determined by heteronuclear multiple-bond correlation experiments. GPL X-IIb was found to be composed of a lipotetrapeptide of the following structure C12-Ser-OMe-Ser-Phe-aThr-OMe (aThr = allothreonine). The sugar part is made up of 3OMe-alpha-L-6dTalp and the following disaccharide: alpha-L-Rhap-(1-->3)-2-O-Lau-alpha-L-Rhap (Rhap = rhanmopyranose). Unlike GPL X-I, the sugar attachment sites on the tetrapeptide were successfully determined from heteronuclear three-bond coupling correlation observed in the heteronuclear multiple bond correlation spectrum between the anomeric carbon resonances and the beta protons of aThr-OMe and Ser. It was established that the 3OMe-6dTalp glycosylates the Ser while the disaccharide is linked to the aThr-OMe. Thus both GPL X-I and GPL X-IIb share a common lipotetrapeptide core [with the exception of Ser(OMe)] but drastically differ in their oligosaccharide appendage. Thus, by analogy with the M. avium complex, the present report suggests that M. xenopi species can be divided in various serovars characterized by the unique structure of their C-mycoside GPL oligosaccharide appendage, enhancing the interest for this new type of serine-containing glycopeptidolipid.