PMID: 2119354Jul 1, 1990Paper

Synthesis of O-glycosylated tuftsins by utilizing threonine derivatives containing an unprotected monosaccharide moiety

International Journal of Peptide and Protein Research
F FiliraR Rocchi

Abstract

Synthesis is described of four tuftsin derivatives containing a D-glucopyranosyl or a D-galactopyranosyl unit covalently linked to the hydroxy side chain function of the threonine residue through either an alpha or beta O-glycosidic linkage. Fmoc-threonine derivatives containing the suitable unprotected sugar were used for incorporating the O-glycosylated amino acid residue. Z-Thr[alpha-Glc(OBzl)4]-OBzl and Z-Thr[alpha-Gal(OBzl)4]-OBzl were prepared from the tetra-O-benzylated sugar and Z-Thr-OBzl by the trichloroacetimidate method in the presence of trimethylsilyl trifluoromethane sulfonate. The alpha glycosylated threonine derivatives were converted into Fmoc-Thr(alpha-Glc)-OH and Fmoc-Thr(alpha-Gal)-OH by catalytic hydrogenation followed by acylation with Fmoc-OSu. beta-Glucosylation and beta-galactosylation of threonine were carried out by reacting the proper per-O-acetylated sugar with Z-Thr-OBzl and boron trifluoride ethyl etherate in dichloromethane. Catalytic hydrogenation of the beta-O-glycosylated threonine derivatives followed by acylation with Fmoc-OSu and deacetylation with methanolic hydrazine yielded Fmoc-Thr(beta-Glc)-OH and Fmoc-Thr(beta-Gal)-OH, respectively. The O-glycosylated threonine derivatives were then ...Continue Reading

References

Jan 24, 1977·Biochimica Et Biophysica Acta·M FridkinZ Spirer
May 1, 1988·International Journal of Peptide and Protein Research·J HorvatP W Schiller
Feb 1, 1987·International Journal of Peptide and Protein Research·R RocchiM Fridkin
May 1, 1980·International Journal of Peptide and Protein Research·C D ChangJ Meienhofer

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Citations

Apr 2, 1998·Journal of Peptide Science : an Official Publication of the European Peptide Society·L BiondiR Rocchi
Apr 28, 2000·The Journal of Peptide Research : Official Journal of the American Peptide Society·S Vichier-GuerreD Cantacuzène
Mar 1, 1991·International Journal of Peptide and Protein Research·R RocchiM Fridkin
Jan 1, 1993·International Journal of Peptide and Protein Research·L BiondiM Fridkin
Jun 1, 1997·The Journal of Peptide Research : Official Journal of the American Peptide Society·S BayD Cantacuzène
Jul 1, 1992·International Journal of Peptide and Protein Research·M GobboT Piek
Mar 1, 1995·International Journal of Peptide and Protein Research·M GobboT Piek
Jan 6, 2010·Chembiochem : a European Journal of Chemical Biology·Søren L PedersenKnud J Jensen
Jun 1, 1994·International Journal of Peptide and Protein Research·M MeldalK Bock
Jul 1, 1994·International Journal of Peptide and Protein Research·M GobboT Piek
Jan 3, 1994·Carbohydrate Research·C UnverzagtJ C Paulson

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