Department of Chemistry, University of Toronto, 80 St George Street, Toronto, ON, M5S 3H6 (Canada) http://www.diaminopharm.com.
Angew Chem Int Ed Engl. 2014 Jan 13;53(3):829-32. doi: 10.1002/anie.201307410. Epub 2013 Nov 27.
The highly stereoselective supramolecular self-assembly of α-amino acids with a chiral aldehyde derived from binol and a chiral guanidine derived from diphenylethylenediamine (dpen) to form the imino acid salt is reported. This system can be used to cleanly convert D-amino acids into L-amino acids or vice versa at ambient temperature. It can also be used to synthesize α-deuterated D- or L-amino acids. A crystal structure of the ternary complex together with DFT computation provided detailed insight into the origin of the stereoselective recognition of amino acids.
报告了手性醛（来源于联二萘酚）和手性胍（来源于二苯乙烯二胺）与α-氨基酸的高对映选择性超分子自组装形成亚氨基盐。该体系可在环境温度下将 D-氨基酸转化为 L-氨基酸，反之亦然。它还可用于合成α-氘代的 D-或 L-氨基酸。三元配合物的晶体结构和 DFT 计算提供了对氨基酸对映选择性识别的详细见解。
