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Synthesis of new ribosylated Asn building blocks as useful tools for glycopeptide and glycoprotein synthesis |
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| Authors: | M Angeles Bonache Francesca Nuti Alexandra Le Chevalier Isaad Feliciana Real-Fernández Mario Chelli Paolo Rovero Anna M Papini |
| Institution: | a Laboratory of Peptide & Protein Chemistry & Biology (PeptLab), Polo Scientifico e Tecnologico, University of Florence, via della Lastruccia 13, I-50019 Sesto Fiorentino (FI), Italy b Dipartimento di Chimica Organica ‘Ugo Schiff’ and CNR-ICCOM, Polo Scientifico e Tecnologico, University of Florence, via della Lastruccia 13, I-50019 Sesto Fiorentino (FI), Italy c Dipartimento di Scienze Farmaceutiche, Polo Scientifico e Tecnologico, University of Florence, Via Ugo Schiff 6, I-50019 Sesto Fiorentino (FI), Italy |
| Abstract: | We performed the first synthesis of new Asn derivatives bearing α- or β-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. |
| Keywords: | N-Glycosylated Asn for SPGPS α- and β-ribofuranose Asn Triazine-based coupling reagent |
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