Ester vs. amide on folding: a case study with a 2-residue synthetic peptide

…, VG Puranik, PR Rajamohanan, GJ Sanjayan

Index: Vijayadas, Kuruppanthara N.; Nair, Roshna V.; Gawade, Rupesh L.; Kotmale, Amol S.; Prabhakaran, Panchami; Gonnade, Rajesh G.; Puranik, Vedavadi G.; Rajamohanan, Pattuparambil R.; Sanjayan, Gangadhar J. Organic and Biomolecular Chemistry, 2013 , vol. 11, # 48 p. 8348 - 8356

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Citation Number: 7

Abstract

Although known for their inferiority as hydrogen-bonding acceptors when compared to amides, esters are often found at the C-terminus of peptides and synthetic oligomers (foldamers), presumably due to the synthetic readiness with which they are obtained using protected peptide coupling, deploying amino acid esters at the C-terminus. When the H- bonding interactions deviate from regularity at the termini, peptide chains tend to “fray ...

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