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Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)

Recognition of alpha-amino acid derivatives by N,N'-dibenzylated S,S-(+)-tetrandrine.

Complexation of free and N-acetylated alpha-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 (1)H-NMR titrations in D(2)O. 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.[1]


  1. Recognition of alpha-amino acid derivatives by N,N'-dibenzylated S,S-(+)-tetrandrine. Lara, K.O., Godoy-Alcantar, C., Eliseev, A.V., Yatsimirsky, A.K. Org. Biomol. Chem. (2004) [Pubmed]
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