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Application of HR-MAS NMR in the solid-phase synthesis of a glycopeptide using Sieber amide resin

✍ Scribed by Luísa R. Carvalho; Marta C. Corvo; Ramu Enugala; M. Manuel B. Marques; Eurico J. Cabrita

Publisher
John Wiley and Sons
Year
2010
Tongue
English
Weight
374 KB
Volume
48
Category
Article
ISSN
0749-1581

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✦ Synopsis

Abstract

The solid‐phase synthesis (SPS) of a structurally complex glycopeptide, using Sieber amide resin, was monitored by high resolution magic angle spinning NMR, demonstrating the further application of this technique. A synthetic peptidoglycan derivative, a precursor of a biologically active PGN, known to be involved in the cellular recognition, was prepared by SPS. The synthesis involved the preparation of an N‐alloc glucosamine moiety and the synthesis of a simple amino acid sequence L‐Ala‐D‐Glu‐L‐Lys‐D‐Ala‐D‐Ala. Last step consisted the coupling, on solid‐phase, of the protected muramyl unit to the peptide chain. Proton spectra with good suppression of the polystyrene signals in swollen resin samples were obtained in DMF‐d~7~ as a solvent and by using a nonselective 1D TOCSY/DIPSI‐2 scheme, thus allowing to follow the SPS without losses of compound and cleavage from the resin. The assignment of the proton spectra of the resin‐bound amino acid sequence and of the bound glycopeptide was achieved through the combination of MAS COSY, TOCSY and NOESY. Copyright © 2010 John Wiley & Sons, Ltd.

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