CyPLOS (cyclic phosphate-linked oligosaccharides), that is, novel cyclic oligosaccharide surrogates, consisting of two, three, and four phenyl-â-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.
Cyclic phosphate-linked oligosaccharides (CYPLOS): synthesis and conformational behaviour of novel oligosaccharide analogues / DI FABIO, Giovanni; Randazzo, Antonio; J., Donofrio; C., Ausin; A., Grandas; E., Pedroso; DE NAPOLI, Lorenzo; Montesarchio, Daniela. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - STAMPA. - 71:9(2006), pp. 3395-3408. [10.1021/jo0600757]
Cyclic phosphate-linked oligosaccharides (CYPLOS): synthesis and conformational behaviour of novel oligosaccharide analogues
DI FABIO, GIOVANNI;RANDAZZO, ANTONIO;DE NAPOLI, LORENZO;MONTESARCHIO, DANIELA
2006
Abstract
CyPLOS (cyclic phosphate-linked oligosaccharides), that is, novel cyclic oligosaccharide surrogates, consisting of two, three, and four phenyl-â-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.File | Dimensione | Formato | |
---|---|---|---|
joc3395-06.pdf
non disponibili
Tipologia:
Documento in Post-print
Licenza:
Accesso privato/ristretto
Dimensione
528.11 kB
Formato
Adobe PDF
|
528.11 kB | Adobe PDF | Visualizza/Apri Richiedi una copia |
I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.