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Design and Synthesis of Triazole based Peptidomimetic Macrocycles and other Heterocycles: Studies on the Self-Assembly and Anion Binding Property of the Macrocycles

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Title Design and Synthesis of Triazole based Peptidomimetic Macrocycles and other Heterocycles: Studies on the Self-Assembly and Anion Binding Property of the Macrocycles
 
Creator Kulsi, Goutam
 
Subject Chemistry
 
Description describes a literature review on several classes of cyclic peptide nanotubes based on cyclic D-,L-,α-peptides, cyclic D-,L-,α,γ peptides and also cyclic-β-peptides. It is focused
on macrodipole modification of cyclic peptides by substituting an amide functional group with a perfect mimic of peptide bond to access more effective artificial ion channels. The major point that came out in this regard was that (1,4)-linked triazole shares a number of features with peptide bond in terms of bond-distance, planarity, H-bond accepting as well as donating ability. This review also contains a short discussion of the basic information about
the advantage of D-glucose derived cis-β-furanoid sugar moiety which has desired structural features to allow the product to attain a conformation conducive for self assembly. The second part of this chapter describes the construction of two types of novel heterocyclic
backbone modified macrocyclic peptides by incorporation of an α-amino acid/β-amino acid with cis-β-furanoid (1,4)-linked triazole amino acid. The macrocyclic peptides featuring α- amino acids are able to maintain pseudo cyclo-β-peptide conformation, while that based on β- amino acid forms only a conformationally homogeneous cyclic peptide. One of the cyclic peptides is able to undergo parallel homo-stacking via amide NH and amide carbonyl oxygen H-bonding like cyclo-β-peptides.
 
Date 2015
 
Type Thesis
NonPeerReviewed
 
Format application/pdf
 
Identifier http://www.eprints.iicb.res.in/2363/1/Thesis_Goutam_Kulsi;2015.pdf
Kulsi, Goutam (2015) Design and Synthesis of Triazole based Peptidomimetic Macrocycles and other Heterocycles: Studies on the Self-Assembly and Anion Binding Property of the Macrocycles. PhD thesis, JU.
 
Relation http://www.eprints.iicb.res.in/2363/