Dimedone‐Based Rigid Organic Scaffold for Organizing Symmetrical Helical Peptide Chains. Issue 39 (21st October 2019)

• Record Type: Journal Article
• Authors: Madica, Krishnaprasad; Lakshmi, Jerripothula K; Madhu, Suresh; Nadimpally, Krishna Chaitanya; Gonnade, Rajesh; Jagadeesh, Bharatam; Sanjayan, Gangadhar J
• Is Part Of: ChemistrySelect. Volume 4:Issue 39(2019)
• Page Start: 11518
• Page End: 11522
• Publication Date: 2019-10-21
• Subjects: Dimedone -- Helical -- Hydrogen bonding -- Peptides -- Template; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/slct.201903087
• Languages: English
• ISSNs: 2365-6549

Abstract

Abstract: We describe herein design, synthesis and conformational investigations of polypeptides attached on a rigid dimedone template. Two identical peptide chains are attached on a single carbon containing dimedone as a scaffold. Dimedone assists in controlling the secondary interactions through strong intramolecular helical C‐12 and C‐15 membered bifurcated hydrogen bonding on both the peptide chains along with propagating the helical architecture of the peptide chains attached. There exists a C‐6 hydrogen bonding for the single stranded peptides attached to dimedone. Extensive structural investigations involving single crystal X‐ray diffraction, solution‐state NMR and CD studies of oligopeptides have been undertaken. Abstract : This paper highlights the design, synthesis and structural investigations of polypeptides attached on a rigid template dimedone. It imparts folding assisted by two carbonyl groups present in the molecule through unusual hydrogen bonding.