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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.

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Title 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.
 
Creator Ghorai, Abhijit
Gayen, Anindita
Kulsi, Goutam
Padmanaban, E
Laskar, Aparna
Achari, Basudeb
Mukhopadhyay, Chaitali
Chattopadhyay, Partha
 
Subject Chemistry
 
Description 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.
 
Publisher American Chemical Society
 
Date 2011
 
Type Article
PeerReviewed
 
Format application/pdf
 
Identifier http://www.eprints.iicb.res.in/1322/1/ORGANIC_LETTERS__Volume_13___Issue_20___Pages_5512%2D5515.pdf
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.
 
Relation http://dx.doi.org/10.1021/ol2022356
http://www.eprints.iicb.res.in/1322/