Simultaneous Parallel and Antiparallel Self-Assembly in a Triazole/Amide Macrocycle Conformationally Homologous to D-,L-r-Amino Acid Based Cyclic Peptides: NMR and Molecular Modeling Study.

Ghorai, Abhijit and Gayen, Anindita and Kulsi, Goutam and Padmanaban, E and Laskar, Aparna and Achari, Basudeb and Mukhopadhyay, Chaitali and Chattopadhyay, Partha (2011) Simultaneous Parallel and Antiparallel Self-Assembly in a Triazole/Amide Macrocycle Conformationally Homologous to D-,L-r-Amino Acid Based Cyclic Peptides: NMR and Molecular Modeling Study. Organic Letters, 13 (20). pp. 5512-5515.

[img]

PDF
Restricted to IICB Scientists only

Download (745Kb) | Request a copy

    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-R-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.

    Item Type: Article
    URI: http://www.eprints.iicb.res.in/id/eprint/1322
    Subjects: Chemistry
    Divisions: Indian Institute of Chemical Biology
    Depositing User: Ms Sutapa Ganguly
    Date Deposited: 31 Jan 2012 12:07
    Last Modified: 06 Jul 2012 11:38
    Official URL: http://dx.doi.org/10.1021/ol2022356
    Links:

    Actions (login required)

    View Item