TY - JOUR
T1 - Simultaneous parallel and antiparallel self-assembly in a triazole/amide macrocycle conformationally homologous to d-, L-α-amino acid based cyclic peptides
T2 - NMR and molecular modeling study
AU - Ghorai, Abhijit
AU - Gayen, Anindita
AU - Kulsi, Goutam
AU - Padmanaban, E.
AU - Laskar, Aparna
AU - Achari, Basudeb
AU - Mukhopadhyay, Chaitali
AU - Chattopadhyay, Partha
PY - 2011/10/21
Y1 - 2011/10/21
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=80054680094&partnerID=8YFLogxK
U2 - 10.1021/ol2022356
DO - 10.1021/ol2022356
M3 - Article
C2 - 21939245
AN - SCOPUS:80054680094
SN - 1523-7060
VL - 13
SP - 5512
EP - 5515
JO - Organic Letters
JF - Organic Letters
IS - 20
ER -