title: Influence of Linker Length on Conformational Preferences of Glycosylated Sugar Amino Acid Foldamers.
abstract: Glycosylation of foldamers derived from furanoid sugar amino acids with mannose and a propyltriazole linker results in an unprecedented 16/10 mixed-turn structure in the glycopeptides in water, with a preference for the higher-order structure irrespective of the stereochemistry of the starting foldamer. This is in stark contrast to the structures displayed by the same oligomers in water when mannosylated with a two-carbon-shorter methyltriazole linker: 16-membered turn structure in the cis-foldamer and 10-membered in its trans congener. This demonstrates the defining influence of the linker length on the structural preference of these novel glycopeptide mimics.
authors.affiliation: Department of Organic Chemistry, Indian Institute of Science, CV Raman Road, Bengaluru, 560012, India.|Medicinal and Process Chemistry Division, CSIR-Central Drug Research Institute, Sector 10, Jankipuram Extension, Sitapur Road, Lucknow, 226031, India.
authors.forename: Yashoda Krishna
authors.initials: YK
authors.lastname: Sunkari
authors.affiliation: Centre for Nuclear Magnetic Resonance, SAIF, CSIR-Central Drug Research Institute, Sector 10, Jankipuram Extension, Sitapur Road, Lucknow, 226031, India.
authors.forename: Faiyaz
authors.initials: F
authors.lastname: Alam
authors.affiliation: Centre for Nuclear Magnetic Resonance, SAIF, CSIR-Central Drug Research Institute, Sector 10, Jankipuram Extension, Sitapur Road, Lucknow, 226031, India.
authors.forename: Pancham Singh
authors.initials: PS
authors.lastname: Kandiyal
authors.affiliation: Laboratoire des Glucides (UMR 6912), CNRS-FRE-3517, Universit de Picardie Jules Verne, 33, Rue St Leu, Faculte des Sciences, Amiens, 80039, France.
authors.forename: Siriwardena
authors.initials: S
authors.lastname: Aloysius
authors.affiliation: Centre for Nuclear Magnetic Resonance, SAIF, CSIR-Central Drug Research Institute, Sector 10, Jankipuram Extension, Sitapur Road, Lucknow, 226031, India. ravi_sa@cdri.res.in.
authors.forename: Ravi Sankar
authors.initials: RS
authors.lastname: Ampapathi
authors.affiliation: Department of Organic Chemistry, Indian Institute of Science, CV Raman Road, Bengaluru, 560012, India. tushar@orgchem.iisc.ernet.in.|Medicinal and Process Chemistry Division, CSIR-Central Drug Research Institute, Sector 10, Jankipuram Extension, Sitapur Road, Lucknow, 226031, India. tushar@orgchem.iisc.ernet.in.
authors.forename: Tushar Kanti
authors.initials: TK
authors.lastname: Chakraborty
mesh_terms: D000596:Amino Acids / Q000737:chemistry*; D000606:Amino Sugars / Q000737:chemistry*; D006020:Glycopeptides / Q000737:chemistry*; D006031:Glycosylation; D008968:Molecular Conformation
chemical_list: D000596:Amino Acids; D000606:Amino Sugars; D006020:Glycopeptides
keywords: NMR spectroscopy; conformation analysis; foldamers; glycoconjugates; linker; sugar amino acid