Adaptive Encapsulation of ω-Amino Acids and Their Guanidinium–Amide Congeners
作者:Wei-Xu Feng、Arie van der Lee、Yves-Marie Legrand、Eddy Petit、Dan Dumitrescu、Cheng-Yong Su、Mihail Barboiu
DOI:10.1021/acs.orglett.6b02802
日期:2016.11.4
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.
5′-C-Tosyloxyalkylnucleosides. Models for Oligonucleotide Coupling with Nucleophiles
作者:V. Banuls、V. Sarramegna、C. Froment、J M. Escudier、L. Gorrichon
DOI:10.1080/07328319908044777
日期:1999.6
5'-C-substituted nucleosides with an hydroxyalkyl chain are synthesized. The stereochemistry of the new stereogenic center is defined. After introduction of a tosyl group, dimer models are prepared to evaluate the conjugation with amines used as nucleophiles.
“Calix[4]-box” cages promote the formation of amide bonds in water in the absence of coupling reagents
作者:Wei-Xu Feng、Liya Dai、Shao-Ping Zheng、Arie van der Lee、Cheng-Yong Su、Mihail Barboiu
DOI:10.1039/c8cc04561e
日期:——
The present work shows that encapsulation can be used to promote amide bond formation in water under mild conditions, in the absence of carbodiimide coupling agents.