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在含有麦角灵骨架的手性固定相上直接拆分旋光异构体。5. 氨基酸衍生物的对映体拆分

Direct resolution of optically active isomers on chiral packings containing ergoline skeletons. 5. Enantioseparation of amino Acid derivatives.

作者信息

Messina A, Girelli A M, Flieger M, Sinibaldi M, Sedmera P, Cvak L

机构信息

Dipartimento di Chimica, Università di Roma "La Sapienza", Piazzale Aldo Moro 5, I-00185 Roma, Italy, Institute of Microbiology, Academy of Sciences of the Czech Republic, Videnskà 1083, C-142 20 Prague 4, Czech Republic, Istituto di Cromatografia, CNR-Area della Ricerca di Roma, P.O. Box 10, I-00016 Monterotondo Stazione, Roma, Italy, and Galena Opava, Opava, Czech Republic.

出版信息

Anal Chem. 1996 Apr 1;68(7):1191-6. doi: 10.1021/ac950698c.

DOI:10.1021/ac950698c
PMID:21619152
Abstract

A new procedure for ergot alkaloid-based chiral stationary phase preparation is described. Synthesis is based on bonding the allyl derivative of terguride to mercaptopropylsilanized silica gel. The packing exhibits higher content of chiral selector, stability, reproducibility, and enantioselectivity toward amino acids compared to that previously studied. The chromatographic behavior of amino acids with different side chains and substituent groups is investigated in order to obtain a deeper insight into the enantiodiscriminative mechanism as well as to determine the limitations and strengths of terguride as a chiral selector for this class of compounds. A variety of factors, including mobile phase parameters such as pH, ionic strength, content and nature of organic modifier, and temperature, are examined.

摘要

描述了一种基于麦角生物碱的手性固定相制备的新方法。合成基于将特古力胺的烯丙基衍生物键合到巯基丙基硅烷化硅胶上。与之前研究的相比,该填料表现出更高的手性选择剂含量、稳定性、重现性以及对氨基酸的对映选择性。研究了具有不同侧链和取代基的氨基酸的色谱行为,以便更深入地了解对映体识别机制,并确定特古力胺作为这类化合物的手性选择剂的局限性和优势。考察了多种因素,包括流动相参数,如pH值、离子强度、有机改性剂的含量和性质以及温度。

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