Cyclic phosphate-linked oligosaccharides: synthesis and conformational behavior of novel cyclic oligosaccharide analogues

The Journal of Organic Chemistry
Giovanni Di FabioDaniela Montesarchio

Abstract

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.

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Citations

Mar 29, 2013·Accounts of Chemical Research·Francesco De RiccardisPaolo Tecilla
May 18, 2016·The Journal of Organic Chemistry·Krishnagopal Maiti, Narayanaswamy Jayaraman
Mar 6, 2009·Organic & Biomolecular Chemistry·Sabina LicenPaolo Tecilla
Nov 6, 2010·Chemistry : a European Journal·Cinzia CoppolaDaniela Montesarchio
Mar 13, 2019·Chembiochem : a European Journal of Chemical Biology·Claudia RiccardiDaniela Montesarchio
Nov 15, 2013·Chemical Communications : Chem Comm·Atchutarao Pathigoolla, Kana M Sureshan
Mar 4, 2008·The Journal of Organic Chemistry·David Rodríguez-LucenaJosé M García Fernandez
Mar 24, 2009·The Journal of Organic Chemistry·David Rodríguez-LucenaJuan M Benito
Nov 30, 2010·Journal of Colloid and Interface Science·Gaetano MangiapiaLuigi Paduano

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