用于测定β-羟基-α-氨基酸衍生物绝对构型的圆二色激子手性法。

CD exciton chirality method for determination of the absolute configuration of beta-hydroxy-alpha-amino acid derivatives.

作者信息

Lo L C, Chen J Y, Yang C T, Gu D S

机构信息

Department of Chemistry, National Taiwan University, Taipei, Taiwan.

出版信息

Chirality. 2001 May 15;13(5):266-71. doi: 10.1002/chir.1029.

DOI:10.1002/chir.1029

PMID:11317348

Abstract

The absolute configuration of beta-hydroxy-alpha-amino acids was studied by CD exciton chirality method using 7-diethylaminocoumarin-3-carboxylate as a red-shifted chromophore. The CD spectra of bischromophoric derivatives of (S)-serine and (2S,3R)-threonine methyl esters (2 and 7) were compared with those of acyclic vic-aminoalcohols and diols (3--6 and 8--9). This study indicates that the polar carboxylate group of beta-hydroxy-alpha-amino acids makes them a unique subclass of vic-aminoalcohols. By combining the data of CD and NMR coupling constants, we are able to correlate their preferred conformer B and positive CD to the corresponding absolute configuration.

摘要

使用7-二乙氨基香豆素-3-羧酸酯作为红移发色团，通过圆二色激子手性方法研究了β-羟基-α-氨基酸的绝对构型。将(S)-丝氨酸和(2S,3R)-苏氨酸甲酯(2和7)的双色团衍生物的圆二色光谱与无环邻氨基醇和二醇(3-6和8-9)的光谱进行了比较。该研究表明，β-羟基-α-氨基酸的极性羧酸基团使其成为邻氨基醇的一个独特子类。通过结合圆二色和核磁共振耦合常数的数据，我们能够将它们的优势构象B和正圆二色与相应的绝对构型关联起来。