Simultaneous parallel and antiparallel self-assembly in a triazole/amide macrocycle conformationally homologous to d-, L-α-amino acid based cyclic peptides: NMR and molecular modeling study

Abhijit Ghorai, Anindita Gayen, Goutam Kulsi, E. Padmanaban, Aparna Laskar, Basudeb Achari, Chaitali Mukhopadhyay, Partha Chattopadhyay

Research output: Contribution to journalArticlepeer-review

31 Scopus citations

Abstract

A 1,4-linked triazole/amide based peptidomimetic macrocycle, synthesized from a triazole amide oligomer of cis-furanoid sugar triazole amino acids, possesses a conformation resembling the d-,l-α-amino acid based cyclic peptides despite having uniform backbone chirality. It undergoes a unique mode of self-assembly through an antiparallel backbone to backbone intermolecular H-bonding involving amide NH and triazole N2/N3 as well as parallel stacking via amide NH and carbonyl oxygen H-bonding, leading to the formation of a tubular nanostructure.

Original languageEnglish
Pages (from-to)5512-5515
Number of pages4
JournalOrganic Letters
Volume13
Issue number20
DOIs
StatePublished - 21 Oct 2011
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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