Synthesis and solution conformation of homo-beta-peptides consisting of N-mannofuranosyl-3-ulosonic acids.
The synthesis and solution conformation of homo-oligomers of beta-aminoacids, beta-N-mannofuranosyl-3-ulosonic acids, have been studied by NMR, MD simulation, and circular dichroism. These oligomers feature a spirocyclic disubstitution and a N,O-acetal functionality at the beta-carbon of the backbone, an unprecedented situation in the realm of beta-peptides. Our study shows that tetramer 10 and hexamer 11 adopt a characteristic secondary structure. In the hexamer 11, NMR investigations coupled with MD simulations suggest the preference for a double C(8) turn forming conformation.
Andreini
Manuel
M
Groupe SUCRES, Nancy Université UMR 7565, Nancy 1-CNRS, BP 70239, F-54506, Nancy-Vandoeuvre, France.
Taillefumier
Claude
C
Chrétien
Françoise
F
Thery
Vincent
V
Chapleur
Yves
Y
D004187:Disaccharides / Q000737:chemistry; D005663:Furans / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008358:Mannose / Q000737:chemistry*; D015394:Molecular Structure; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry*; D012996:Solutions / Q000737:chemistry
D004187:Disaccharides; D005663:Furans; D010455:Peptides; D012996:Solutions; C064987:heptose-3-deoxyoctulosonic acid; D008358:Mannose