利用具有二维手性的固体表面对沙利度胺对映体进行手性识别。

Chiral discrimination between thalidomide enantiomers using a solid surface with two-dimensional chirality.

作者信息

Nakanishi Takuya, Yamakawa Naoko, Asahi Toru, Shibata Norio, Ohtani Bunsho, Osaka Tetsuya

机构信息

Department of Applied Chemistry, School of Science and Engineering, Waseda University, Tokyo, Japan.

出版信息

Chirality. 2004;16 Suppl:S36-9. doi: 10.1002/chir.20039.

DOI:10.1002/chir.20039

PMID:15239071

Abstract

Chiral discrimination between thalidomide enantiomers was achieved using the self-assembled monolayer (SAM) of an atropisomeric compound, 1,1'-binaphthalene-2,2'-dithiol (BNSH), which takes a two-dimensional chiral arrangement on gold(111) surface. Interestingly, an "all-or-none" type enantioselectivity appears; one enantiomeric form of BNSH SAM allows the adsorption of only one enantiomer of thalidomide. In addition, the response of a racemic SAM of BNSH was revealed to be one-half of that caused by pure enantiomeric SAM.

摘要

利用阻转异构化合物1,1'-联萘-2,2'-二硫醇（BNSH）的自组装单分子层（SAM）实现了沙利度胺对映体之间的手性识别，该化合物在金（111）表面呈二维手性排列。有趣的是，出现了一种“全或无”型对映选择性；BNSH SAM的一种对映体形式仅允许沙利度胺的一种对映体吸附。此外，BNSH外消旋SAM的响应被发现是由纯对映体SAM引起的响应的一半。