Adaptive Encapsulation of omega-Amino Acids and Their Guanidinium-Amide Congeners

作者:Feng, Wei Xu; van der Lee, Arie; Legrand, Yves Marie; Petit, Eddy; Dumitrescu, Dan; Su, Cheng Yong; Barboiu, Mihail*
来源:Organic Letters, 2016, 18(21): 5556-5559.
DOI:10.1021/acs.orglett.6b02802

摘要

The binding and the encapsulation of the 6-aminohexanoic acid (1) and 11-aminoundecanoic acid (2) are achieved in aqueous solution and in crystalline Pyrene-box cages. Unexpectedly, the amino-guanidinium AG( ) and the amino acids 1 or 2 are reacting in aqueous solution in the absence and in the presence of Pyrene-box cages. The formation of an amide bond between a carboxylic acid and the amino-guanidine unit under mild acidic conditions in water without the use a coupling reagent is extremely interesting and unexpected. The resulted adducts AG1 and AG2 show adaptive binding behaviors and compressions.