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Issue 12, 2004
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Recognition of α-amino acid derivatives by N,N′-dibenzylated S,S-(+)-tetrandrine

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Abstract

Complexation of free and N-acetylated α-amino acid anions (Gly, Ala, Phe) and some structurally related guests by a dicationic cyclophane-type N,N′-dibenzylated chiral derivative of a bisisoquinoline macrocyclic alkaloid S,S-(+)-tetrandrine (DBT) has been studied by 1H-NMR titrations in D2O. In contrast to other macrocyclic hosts like cyclodextrins and calixarenes, DBT shows highest affinity and large enantioselectivity (K(S)/K(R) ≥ 10) toward smaller N-acetylalanine and binds larger phenylalanine derivatives more weakly and non-selectively. With 1,2,3,4-tetrahydroisoquinoline-3-carboxylate, a rigid analog of phenylalanine, binding again becomes enantioselective with K(S)/K(R) = 3.8. The binding specificity of DBT is rationalized on the basis of molecular mechanics calculations.

Graphical abstract: Recognition of α-amino acid derivatives by N,N′-dibenzylated S,S-(+)-tetrandrine

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Article information


Submitted
23 Feb 2004
Accepted
05 May 2004
First published
21 May 2004

Org. Biomol. Chem., 2004,2, 1712-1718
Article type
Paper

Recognition of α-amino acid derivatives by N,N′-dibenzylated S,S-(+)-tetrandrine

K. O. Lara, C. Godoy-Alcántar, A. V. Eliseev and A. K. Yatsimirsky, Org. Biomol. Chem., 2004, 2, 1712
DOI: 10.1039/B402698E

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