Conformation Analysis of GalNAc‐Appended Sugar Amino Acid Foldamers as Glycopeptide Mimics

Sunkari, Yashoda Krishna ; Pulukuri, Kiran Kumar ; Kandiyal, Pancham Singh ; Vaishnav, Jayanti ; Ampapathi, Ravi Sankar ; Chakraborty, Tushar Kanti (2018) Conformation Analysis of GalNAc‐Appended Sugar Amino Acid Foldamers as Glycopeptide Mimics ChemBioChem, 19 (14). pp. 1507-1513. ISSN 1439-4227

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Official URL: http://doi.org/10.1002/cbic.201800087

Related URL: http://dx.doi.org/10.1002/cbic.201800087

Abstract

Sugar amino acid (SAA)-based foldamers with well-defined secondary structures were appended with N-acetylgalactosamine (GalNAc) sugars to access sequence-defined, multidentate glycoconjugates with full control over number, spacing and position. Conformation analysis of these glycopeptides by extensive NMR spectroscopic studies revealed that the appended GalNAc units had a profound influence on the native conformational behaviour of the SAA foldamers. Whereas the 2,5-cis glycoconjugate showed a helical structure in water, comprising of two consecutive 16-membered hydrogen bonds, its 2,5-trans congener displayed an unprecedented 16/10-mixed turn structure not seen before in any glycopeptide foldamer.

Item Type:Article
Source:Copyright of this article belongs to John Wiley & Sons, Inc
ID Code:131082
Deposited On:02 Dec 2022 10:02
Last Modified:02 Dec 2022 10:02

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