Hetaryleneaminopolyols and hetarylenecarbopeptoids: a new type of glyco- and peptidomimetics. Syntheses and studies on solution conformation and dynamics.
Ready access to a new class of oligomers has been demonstrated by the synthesis of hetaryleneaminopolyols and hetarylenecarbopeptoids using 3-hydroxymethyl-5-(4-amino-4-deoxy-d-arabinotetritol-1-yl)-2-methylfuran and 5-(4-amino-4-deoxy-d-arabinotetritol-1-yl)-2-methyl-3-furoic acid as novel scaffolds. The conformational behavior of peptidomimetics 22, 23, 25, 26, and 36 have been analyzed by NMR spectroscopy and extensive molecular dynamics simulations. MD simulations using the GB/SA continuum solvent model for water and the MM3 force field provide a population distribution of conformers which satisfactorily agrees with the experimental NMR data for the torsional degrees of freedom of the molecule.
Moreno-Vargas
Antonio J
AJ
Departamento de Química Orgánica, Facultad de Química, Universidad de Sevilla, Apartado 553, Spain.
Jiménez-Barbero
Jesús
J
Robina
Inmaculada
I
D000596:Amino Acids / Q000737:chemistry; D002241:Carbohydrates / Q000737:chemistry*; D020650:Combinatorial Chemistry Techniques; D003198:Computer Simulation; D005663:Furans / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D008968:Molecular Conformation; D018716:Molecular Mimicry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D011108:Polymers / Q000138:chemical synthesis* / Q000737:chemistry*; D011506:Proteins / Q000737:chemistry*; D013237:Stereoisomerism
D000596:Amino Acids; D002241:Carbohydrates; D005663:Furans; D011108:Polymers; D011506:Proteins; C024617:polyol