title: 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.
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.
authors.affiliation: Chemistry Division, Indian Institute of Chemical Biology (CSIR), Kolkata, 700032, India.
authors.forename: Abhijit
authors.initials: A
authors.lastname: Ghorai
authors.forename: Anindita
authors.initials: A
authors.lastname: Gayen
authors.forename: Goutam
authors.initials: G
authors.lastname: Kulsi
authors.forename: E
authors.initials: E
authors.lastname: Padmanaban
authors.forename: Aparna
authors.initials: A
authors.lastname: Laskar
authors.forename: Basudeb
authors.initials: B
authors.lastname: Achari
authors.forename: Chaitali
authors.initials: C
authors.lastname: Mukhopadhyay
authors.forename: Partha
authors.initials: P
authors.lastname: Chattopadhyay
mesh_terms: D000577:Amides / Q000737:chemistry*; D000596:Amino Acids / Q000737:chemistry*; D018360:Crystallography, X-Ray; D047028:Macrocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D008968:Molecular Conformation; D015394:Molecular Structure; D049329:Nanostructures; D010456:Peptides, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D014230:Triazoles / Q000737:chemistry*
chemical_list: D000577:Amides; D000596:Amino Acids; D047028:Macrocyclic Compounds; D010456:Peptides, Cyclic; D014230:Triazoles