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Rational Construction of Triazole/Urea Based Peptidomimetic Macrocycles as Pseudocyclo-β-peptides and Studies on Their Chirality Controlled Self-Assembly

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journal contribution
posted on 20.06.2014, 00:00 by Abhijit Ghorai, Samanth Reddy K, Basudeb Achari, Partha Chattopadhyay
A tandem macro-dimerization reaction via a Cu­(I) catalyzed azide/alkyne cycloaddition reaction has been employed to construct triazole/urea based peptidomimetic macrocycles considered as pseudocyclo-β-peptides. Introduction of one particular chirality in the peptide backbone can alter the conformation as well as nature of self-assembly from cyclic d-,l-,α-peptide to cyclo-β-peptide. One of them (16a) forms antiparallel dimers while the other (16b) undergoes higher order aggregation to form a nanorod structure.