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

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

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Official URL: https://dx.doi.org/10.1002/cbic.201800087


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: Journal Article
Additional Information: Copyright of this article belong to WILEY-V C H VERLAG GMBH, POSTFACH 101161, 69451 WEINHEIM, GERMANY
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Depositing User: Id for Latest eprints
Date Deposited: 09 Aug 2018 15:40
Last Modified: 09 Aug 2018 15:40
URI: http://eprints.iisc.ac.in/id/eprint/60390

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