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A mechanistic study of enantiomeric separation with vancomycin and balhimycin as chiral selectors by capillary electrophoresis. Dimerization and enantioselectivity
其他题名万古霉素和巴里霉素作为毛细管电泳手性分离选择剂的机理研究。双聚作用和对映体选择性的关系
Kang JW(康经武); Daniel Bischoff; Jiang ZJ(江正谨); Bojan Bister; Roderich D. Süssmuth; Volker Schurig
2004
发表期刊Anal. Chem.
ISSN0003-2700
卷号76期号:8页码:2387-2392
摘要The role of the sugar moiety of glycopeptide antibiotics in chiral recognition was investigated with capillary electrophoresis. Two glycopeptide antibiotics, vancomycin and balhimycin, were employed as models since they possess the same aglycon and almost identical sugar moieties, however, with different attachment sites to the aglycon. The observed enantioselectivity of balhimycin for dansylated a-amino acids is 2.6 times higher than that of vancomycin. Blocking of the sugar amino group of balhimycin by N-carbamoylation reaction with KOCN led to a significantly decreased enantioselectivity compared to vancomycin, which remained almost the same upon carbamoylation. These results suggest a major role of the amino sugar together with its site of attachment to the aglycon. A dimerization-based mechanism is proposed to explain this phenomenon due to the fact that the dimerization properties of glycopeptides are similarly related to their glycosylation patterns; e.g., the dimerization constant of balhimycin is 78 times higher than that of vancomycin. Furthermore, the dimerization of glycopeptides promotes their affinity to carboxyl-containing ligands via cooperativity effects between the dimerization and the formation of glycopeptide-ligand complexes. The higher dimer stability probably leads to a more favorable conformation for chiral recognition. Thus, it is concluded that a weakened dimerization of N-carbamoylated balhimycin results in a decreased enantioselectivity.
学科领域分析化学
部门归属中国科学院上海有机化学研究所; 德国图比根大学有机化学研究所
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收录类别SCI
语种英语
WOS记录号WOS:000221096800030
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被引频次:43[WOS]   [WOS记录]     [WOS相关记录]
文献类型期刊论文
条目标识符http://ir.sioc.ac.cn/handle/331003/27589
专题上海有机化学研究所
通讯作者Kang JW(康经武); Volker Schurig
推荐引用方式
GB/T 7714
Kang JW,Daniel Bischoff,Jiang ZJ,et al. A mechanistic study of enantiomeric separation with vancomycin and balhimycin as chiral selectors by capillary electrophoresis. Dimerization and enantioselectivity[J]. Anal. Chem.,2004,76(8):2387-2392.
APA 康经武,Daniel Bischoff,江正谨,Bojan Bister,Roderich D. Süssmuth,&Volker Schurig.(2004).A mechanistic study of enantiomeric separation with vancomycin and balhimycin as chiral selectors by capillary electrophoresis. Dimerization and enantioselectivity.Anal. Chem.,76(8),2387-2392.
MLA 康经武,et al."A mechanistic study of enantiomeric separation with vancomycin and balhimycin as chiral selectors by capillary electrophoresis. Dimerization and enantioselectivity".Anal. Chem. 76.8(2004):2387-2392.
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