Rational construction of triazole/urea based peptidomimetic macrocycles as pseudocyclo-β-peptides and studies on their chirality controlled self-assembly

Abhijit Ghorai; Samanth Reddy K; Basudeb Achari; Partha Chattopadhyay

doi:10.1021/ol501172d

Rational construction of triazole/urea based peptidomimetic macrocycles as pseudocyclo-β-peptides and studies on their chirality controlled self-assembly

Abhijit Ghorai, Samanth Reddy K, Basudeb Achari, Partha Chattopadhyay

Research output: Contribution to journal › Article › peer-review

13 Scopus citations

Abstract

A tandem macro-dimerization reaction via a Cu(I) catalyzed azide/alkyne cycloaddition reaction has been employed to construct triazole/urea based peptidomimetic macrocycles considered as pseudocyclo-β-peptides. Introduction of one particular chirality in the peptide backbone can alter the conformation as well as nature of self-assembly from cyclic d-,l-,α- peptide to cyclo-β-peptide. One of them (16a) forms antiparallel dimers while the other (16b) undergoes higher order aggregation to form a nanorod structure.

Original language	English
Pages (from-to)	3196-3199
Number of pages	4
Journal	Organic Letters
Volume	16
Issue number	12
DOIs	https://doi.org/10.1021/ol501172d
State	Published - 20 Jun 2014
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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abstract = "A tandem macro-dimerization reaction via a Cu(I) catalyzed azide/alkyne cycloaddition reaction has been employed to construct triazole/urea based peptidomimetic macrocycles considered as pseudocyclo-β-peptides. Introduction of one particular chirality in the peptide backbone can alter the conformation as well as nature of self-assembly from cyclic d-,l-,α- peptide to cyclo-β-peptide. One of them (16a) forms antiparallel dimers while the other (16b) undergoes higher order aggregation to form a nanorod structure.",

author = "Abhijit Ghorai and {Reddy K}, Samanth and Basudeb Achari and Partha Chattopadhyay",

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AU - Reddy K, Samanth

AU - Achari, Basudeb

AU - Chattopadhyay, Partha

PY - 2014/6/20

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AB - A tandem macro-dimerization reaction via a Cu(I) catalyzed azide/alkyne cycloaddition reaction has been employed to construct triazole/urea based peptidomimetic macrocycles considered as pseudocyclo-β-peptides. Introduction of one particular chirality in the peptide backbone can alter the conformation as well as nature of self-assembly from cyclic d-,l-,α- peptide to cyclo-β-peptide. One of them (16a) forms antiparallel dimers while the other (16b) undergoes higher order aggregation to form a nanorod structure.

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Rational construction of triazole/urea based peptidomimetic macrocycles as pseudocyclo-β-peptides and studies on their chirality controlled self-assembly

Abstract

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