Folding control of a non-natural glycopeptide using saccharide-coded structural information for polypeptides

We synthesized "glyco-arylopeptides", whose folding structure significantly changes depending on the kind of saccharide in their side chain. The saccharide moiety interacts with the main chain via hydrogen bonding, and the non-natural polypeptides form two well-defined architectures-( P )-...

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Published inChemical communications (Cambridge, England) Vol. 56; no. 18; pp. 2767 - 277
Main Authors Ishido, Yuki, Kanbayashi, Naoya, Fujii, Naoka, Okamura, Taka-aki, Haino, Takeharu, Onitsuka, Kiyotaka
Format Journal Article
LanguageEnglish
Published England Royal Society of Chemistry 04.03.2020
Subjects
Antibiotics
Carbohydrates
Chains
Density Functional Theory
Folding
Folding structures
Glycopeptides
Glycopeptides - chemistry
Helices
Hydrogen bonding
Infrared spectroscopy
Molecular Structure
NMR
Nuclear magnetic resonance
Oligosaccharides - chemistry
Peptides - chemical synthesis
Peptides - chemistry
Polypeptides
Protein Folding
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Summary:We synthesized "glyco-arylopeptides", whose folding structure significantly changes depending on the kind of saccharide in their side chain. The saccharide moiety interacts with the main chain via hydrogen bonding, and the non-natural polypeptides form two well-defined architectures-( P )-3 1 - and ( M )-4 1 -helices-depending on the length of the saccharide chains and even the configuration of a single stereo-genic center in the epimers. We synthesized "glyco-arylopeptides", whose folding structure significantly changes depending on the kind of saccharide in their side chain. The saccharide moiety interacts with the main chain via hydrogen bonding, and the non-natural polypeptides form two well-defined architectures-( P )-3 1 - and ( M )-4 1 -helices-depending on the length of the saccharide chains and even the configuration of a single stereo-genic center in the epimers.
Bibliography:10.1039/c9cc10030j
Electronic supplementary information (ESI) available: Materials, experimental details, spectroscopic data (CD/UV, NMR and IR spectra) and computational study. See DOI
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1359-7345
1364-548X
DOI:10.1039/c9cc10030j