We performed the first synthesis of new Asn derivatives bearing alpha- or beta-ribose as pure anomers, linked by an N-glycosidic bond, on the side chain of the Asn residue orthogonally protected for Fmoc/tBu SPPS, by an efficient five-step strategy with a global yield of 73% starting from D-ribose. These building blocks are obtained in a large scale and can be useful tools for glycopeptide and glycoproteins synthesis.
Synthesis of new ribosylated Asn building blocks as useful tools for glycopeptide and glycoprotein synthesis / M.A. Bonache; F. Nuti; A. Le Chevalier Isaad; F. Real-Fernández; M. Chelli; P. Rovero; A.M. Papini. - In: TETRAHEDRON LETTERS. - ISSN 0040-4039. - STAMPA. - 50:(2009), pp. 4151-4153. [10.1016/j.tetlet.2009.04.124]
Synthesis of new ribosylated Asn building blocks as useful tools for glycopeptide and glycoprotein synthesis.
NUTI, FRANCESCA;ROVERO, PAOLO;PAPINI, ANNA MARIA
2009
Abstract
We performed the first synthesis of new Asn derivatives bearing alpha- or beta-ribose as pure anomers, linked by an N-glycosidic bond, on the side chain of the Asn residue orthogonally protected for Fmoc/tBu SPPS, by an efficient five-step strategy with a global yield of 73% starting from D-ribose. These building blocks are obtained in a large scale and can be useful tools for glycopeptide and glycoproteins synthesis.
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