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基于固定化α-糜蛋白酶的手性固定相高效液相色谱法对映体和非对映体二肽的立体化学识别

Stereochemical recognition of enantiomeric and diastereomeric dipeptides by high-performance liquid chromatography on a chiral stationary phase based upon immobilized alpha-chymotrypsin.

作者信息

Jadaud P, Wainer I W

机构信息

St. Jude Children's Research Hospital, Memphis, TN 38105.

出版信息

J Chromatogr. 1989 Aug 4;476:165-74. doi: 10.1016/s0021-9673(01)93866-x.

DOI:10.1016/s0021-9673(01)93866-x
PMID:2777971
Abstract

A series of 24 enantiomeric and diastereomeric dipeptides were chromatographed on a chiral stationary phase (CSP) based upon immobilized alpha-chymotrypsin (ACHT). The ACHT-CSP was able to resolve stereochemically a number of the enantiomeric D,D- and L,L-dipeptides as well as the diastereomeric D,D-/L,L- and L,D-/D,L-dipeptides. The solutes were also chromatographed on a N-tosyl-L-phenylalanine chloromethyl ketone-deactivated form of the ACHT-CSP, where stereochemical separations were also achieved. The results of this study suggest that binding interactions between the dipeptides and the ACHT-CSP occur at the active site of the ACHT and at other hydrophobic sites on the ACHT molecule.

摘要

一系列24种对映体和非对映体二肽在基于固定化α-胰凝乳蛋白酶(ACHT)的手性固定相(CSP)上进行了色谱分析。ACHT-CSP能够立体化学拆分多种对映体D,D-和L,L-二肽以及非对映体D,D-/L,L-和L,D-/D,L-二肽。这些溶质还在ACHT-CSP的N-甲苯磺酰-L-苯丙氨酸氯甲基酮失活形式上进行了色谱分析,在那里也实现了立体化学分离。本研究结果表明,二肽与ACHT-CSP之间的结合相互作用发生在ACHT的活性位点以及ACHT分子上的其他疏水位点。

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