Cyclic phosphate-linked oligosaccharides: synthesis and conformational behavior of novel cyclic oligosaccharide analogues.
CyPLOS (cyclic phosphate-linked oligosaccharides), that is, novel cyclic oligosaccharide surrogates, consisting of two, three, and four phenyl-beta-D-glucopyranoside units, 4,6-linked through stable phosphodiester bonds, were prepared by a straightforward and efficient solid-phase protocol. The assembly of the linear precursors was achieved by standard phosphoramidite chemistry on an automated DNA synthesizer, using a suitably protected 4-phosphoramidite derivative of D-glucose as the building block. For the crucial cyclization step a phosphotriester methodology was exploited, followed by a mild basic treatment releasing the desired cyclic molecules in solution in a highly pure form. The cyclic dimer and trimer were also independently prepared by classical solution synthesis, basically following the same approach. The solution structural preferences of the cyclic dimer and trimer, obtained by detailed NMR analysis, are also reported.
Di Fabio
Giovanni
G
Dipartimento di Chimica Organica e Biochimica, Università degli Studi di Napoli Federico II, Complesso Universitario di Monte S. Angelo, via Cynthia, 4, I-80126 Napoli, Italy.
Randazzo
Antonio
A
D'Onofrio
Jennifer
J
Ausín
Cristina
C
Pedroso
Enrique
E
Grandas
Anna
A
De Napoli
Lorenzo
L
Montesarchio
Daniela
D
D003577:Cytochrome P-450 Enzyme System; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D010710:Phosphates; D010940:Plant Proteins
D009844:Oligosaccharides; D010710:Phosphates; D010940:Plant Proteins; D003577:Cytochrome P-450 Enzyme System