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Structural Insights into the Hydrogen‐Bonding and Folding Pattern in Ant‐Ant‐Pro‐Gly Tetrapeptides
Author(s) -
Baravkar Sachin B.,
Kotmale Amol S.,
Shaikh Samir R.,
Gonnade Rajesh G.,
Sanjayan Gangadhar J.
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201700181
Subject(s) - chemistry , hydrogen bond , ant , amide , folding (dsp implementation) , stereochemistry , glycine , molecular dynamics , amino acid , molecule , computational chemistry , biochemistry , organic chemistry , computer science , electrical engineering , engineering , computer network
In this paper, we provide structural insights into the hydrogen‐bonding and folding pattern in Ant‐Ant‐Pro‐Gly tetrapeptides (Ant: anthranilic acid; Pro: proline; and Gly: glycine). Comparison of the C‐terminal esters and their amide analogs revealed strikingly different H‐bonding networks. Whereas the ester analogs displayed an open structure without terminal H‐bonding interactions, the amide analogs showed a completely folded structure. Structural details were revealed by using a combination of X‐ray crystal structure studies and NOE‐based molecular dynamics (MD) simulation studies.