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A highly convergent approach to O- and N-linked glycopeptides analogues
Authors:Francesco Peri  Laura Cipolla  Barbara La Ferla  Pascal Dumy  Francesco Nicotra
Affiliation:(1) Department of Biotechnology and Biosciences, University of Milano-Bicocca, Via Emanueli 12, I-20126 Milano;(2) LEDSS-5, University J. Fourier, 301 Rue de la Chimie, BP 53, F-38041 Grenoble cedex 9
Abstract:
Deprotected C-glycopyranosyl-ketones have been conjugated by a chemoselective approach to a peptide or an amino acid bearing an aminooxy group on the N-terminus or on the side-chain, respectively. The coupling reaction, performed in aqueous media, does not require protecting groups on the peptide or saccharide moieties, nor auxiliary coupling reagents.
Keywords:glycomimetics  C-glycosides  glycopeptides  chemoselective ligation  Aoa, aminooxyacetyl  Boc, tert-Butoxycarbonyl  Dpr,   /content/k3426j363nj40172/xxlarge945.gif"   alt="  agr"   align="  BASELINE"   BORDER="  0"  >,  /content/k3426j363nj40172/xxlarge946.gif"   alt="  beta"   align="  MIDDLE"   BORDER="  0"  >-L-Diaminopropionic acid  DIPEA, Diisopropylethylamine  DMF, N,N-Dimethylformamide  Fmoc, 9-Fluorenylmethoxycarbonyl  PyBOP, Benzotriazole-1-yl-oxy-tris-pyrrolidino-phosphonium hexafluorophosphate
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