The Journal of organic chemistry

Molecular discrimination of N-protected amino acid esters by a self-assembled cylindrical capsule: spectroscopic and computational studies

O Hayashida, L Sebo, J Rebek

Index: Hayashida, Osamu; Sebo, Lubomir; Rebek Jr., Julius The Journal of organic chemistry, 2002 , vol. 67, # 24 p. 8291 - 8298

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Citation Number: 67

Abstract

A self-assembled, cylindrical capsule was used to bind N-α-protected amino acid esters. The reversible encapsulation was studied using NMR spectroscopy in deuterated mesitylene solution and by computer-aided molecular modeling. BOC-l-alanine alkyl esters and BOC-β- alanine alkyl esters were tested as guests, and the relative binding affinities were established by direct competition experiments. A good correlation was found between the ...