Synthesis of Fully O-Benzylated N-Linked Core Pentasaccharide Glycosyl Azide

REFERENCES

• Dwek , R. A. 1996 . Glycobiology: toward understanding the function of sugars . Chem. Rev. , 96 : 683 – 720 .
   PubMed Web of Science ®Google Scholar
• Varki , A. 1993 . Biological roles of oligosaccharides: all of the theories are correct . Glycobiology , 3 : 97 – 130 .
   PubMed Web of Science ®Google Scholar
• Knight , P. 1989 . The carbohydrate frontier . Biotechnology , 7 : 35 – 40 .
   Google Scholar
• Mandal , M. , Dudkin , V. Y. , Geng , X. and Danishefsky , S. J. 2004 . In pursuit of carbohydrate-based HIV vaccines, part 1: The total synthesis of high-mannose-type gp120 fragments . Angew. Chem. Int. Ed. , 43 : 2557 – 2561 .
   PubMed Web of Science ®Google Scholar
• Bennett , C. S. and Wong , C.-H. 2007 . Chemoenzymatic approaches to glycoprotein synthesis . Chem. Soc. Rev. , 36 : 1227 – 1238 .
   Web of Science ®Google Scholar
• Gamblin , D. P. , Scanlan , E. M. and Davis , B. G. 2009 . Glycoprotein synthesis: an update . Chem. Rev. , 109 : 131 – 163 .
   PubMed Web of Science ®Google Scholar
• Davis , B. G. 2002 . Synthesis of glycoproteins . Chem. Rev. , 102 : 579 – 601 .
   PubMed Web of Science ®Google Scholar
• Buskas , T. , Ingale , S. and Boons , G. J. 2006 . Glycopeptides as a versatile tool for glycobiology . Glycobiology , 16 : 113R – 136R .
   Web of Science ®Google Scholar
• Kan , C. and Danishefsky , S. J. 2009 . Recent departures in the synthesis of peptides and glycopeptides . Tetrahedron , 65 : 9047 – 9065 .
   Web of Science ®Google Scholar
• Pudelko , M. , Bull , J. and Kunz , H. 2010 . Chemical and chemo-enzymatic synthesis of glycopeptide selectin ligands containing sialyl Lewis X structures . Chembiochem , 11 : 904 – 930 .
   Web of Science ®Google Scholar
• Payne , R. J. and Wong , C.-H. 2010 . Advances in chemical ligation strategies for the synthesis of glycopeptides and glycoproteins . Chem. Commun. , 46 : 21 – 43 .
   PubMed Web of Science ®Google Scholar
• Kerékgyártó , J. , Ágoston , K. , Batta , Gy. , Kamerling , J. P. and Vliegenthart , J. F.G. 1998 . Synthesis of fully and partially benzylated glycosyl azides via thioalkyl glycosides as precursors for the preparation of N-glycopeptides . Tetrahedron Lett. , 39 : 7189 – 7192 .
   Web of Science ®Google Scholar
• Tóth , G. , Kádár , K. , Hegyi , O. , Csikós , O. , Kalmár , L. and Kerékgyártó , J. 2008 . Glycopeptides-a synthetic challenge . J. Pept. Res. , 14 ( 8 ) : 71 – 72 .
   Google Scholar
• Tóth , G. , Kádár , K. , Hegyi , O. , Csikós , O. , Kalmár , L. , Kerékgyártó , J. , Kerékgyártó , J. , Kalmár , L. , Szurmai , Z. , Harangi , J. , Hegyi , O. and Tóth , G. K. 2008 . Glycopeptides-a synthetic challenge. Part I (c) Glycopeptides-a synthetic challenge. Part II. Proceedings of the 4th Central European Conference Chemistry towards Biology, Dobogókő, Hungary, September 8-11
   Google Scholar
• Tóth , G. , Kádár , K. , Hegyi , O. , Csikós , O. , Kalmár , L. and Kerékgyártó , J . 2008 . Glycopeptides-a synthetic challenge. Part I. Proceedings of the 4th Central European Conference Chemistry towards Biology 41 Dobogókő , , Hungary September 8-11
   Google Scholar
• Kerékgyártó , J. , Kalmár , L. , Szurmai , Z. , Harangi , J. , Hegyi , O. and Tóth , G. K . 2008 . Glycopeptides-a synthetic challenge. Part II. Proceedings of the 4th Central European Conference Chemistry towards Biology 42 Dobogókő , , Hungary September 8-11
   Google Scholar
• Szolomajer-Csikós , O. Sz.Cs. , Rákosi , K. , Hegyi , O. , Kalmár , L. , Kerékgyártó , J. and Tóth , G. 2010 . The application of the new tin (IV) chloride deprotection for the preparation of glycosylated peptides . J. Pept. Res. , 16 ( 1 ) : 57 – 58 .
   Google Scholar
• Kádár , K. , Hegyi , O. , Csikós , O. , Tóth , G. K. , Kalmár , L. , Szurmai , Z. and Kerékgyártó , J. 2011 . Synthesis of N-glycopeptides applying glycoamino acid building blocks with a combined Fmoc/Boc strategy . Protein Peptide Lett. , 18 : 679 – 683 .
   Web of Science ®Google Scholar
• Crich , D. and Sun , S. 1997 . Direct synthesis of β-mannospyranosides by the sulfoxide method . J. Org. Chem. , 62 : 1198 – 1199 .
   Web of Science ®Google Scholar
• Ochiai , H. , Huang , W. and Wang , L-X. 2008 . Expeditious chemoenzymatic synthesis of homogeneous N-glycoproteins carrying defined oligosaccharide ligands . J. Am. Chem. Soc. , 130 : 13790 – 13803 .
   Web of Science ®Google Scholar
• Wang , P. , Zhu , Y. , Yuan , Y. and Danishefsky , S. J. 2009 . Total synthesis of the 2,6-sialylated immunoglobulin G glycopeptides fragment in homogeneous form . J. Am. Chem. Soc. , 131 : 16669 – 16671 .
   Web of Science ®Google Scholar
• Pozsgai , V. 2000 . “ Stereoselective synthesis of β-mannosides ” . In Carbohydrates in Chemistry and Biology , Edited by: Ernst , B. , Hart , G. W. and Sinaÿ , P. 319 – 343 . Wiley-VCH .
   Google Scholar
• Matsuo , I. , Nakahara , Y. , Ito , Y. , Nukada , T. , Nakahara , Y. and Ogawa , T. 1995 . Synthesis of a glycopeptide carrying a N-linked core pentasaccharide . Bioorg. Med. Chem. , 3 : 1455 – 1463 .
   PubMed Web of Science ®Google Scholar
• Danishefsky , S. J. , Hu , S. , Cirillo , P. F. , Eckhardt , M. and Seeberger , P. H. 1997 . A highly convergent synthetic route to glycopeptides carrying a high mannose core pentasaccharide domain N-linked to a natural peptide motif . Chem. Eur. J. , 3 : 1617 – 1628 .
   Web of Science ®Google Scholar
• Matsuo , I. , Isomura , M. and Ajisaka , K. 1999 . Synthesis of an asparagine-linked core pentasaccharide by means of simultaneous inversion reactions . J. Carbohydr. Chem. , 18 : 841 – 850 .
   Web of Science ®Google Scholar
• Pratt , M. J. and Bertozzi , C. R. 2003 . Chemoselective ligation applied to the synthesis of a biantennary N-linked glycoform of CD52 . J. Am. Chem. Soc. , 125 : 6149 – 6159 .
   PubMed Web of Science ®Google Scholar
• Cunningam , J. , Gigg , R. and Warren , C. D. 1964 . The allyl ether as a protecting group in carbohydrate chemistry . Tetrahedron Lett. , 5 : 1191 – 1196 .
   Google Scholar
• Kunz , H. and Günther , W. 1988 . β-mannoside aus β-glucosiden durch intramoleculare nuchleophil substitution unter konfigurationsumkehr . Angew. Chem. , 100 : 1118 – 1119 .
   Google Scholar
• Nilsson , M. and Norberg , T. 1990 . Synthesis of a monofucosyl heptasaccharide corresponding to a tumor-associated glycolipid defined by monoclonal antibody ACFH-18 . J. Carbohydr. Chem. , 9 : 1 – 14 .
   Web of Science ®Google Scholar
• Kerékgyártó , J. , Rákó , J. , Ágoston , K. , Gyémánt , Gy. and Szurmai , Z. 2000 . New factors governing stereoselectivity in borohydride reductions of β-D-glycoside-2-uloses. The peculiar effect of “activated” DMSO . Eur. J. Org. Chem. , 23 : 3931 – 3935 .
   Google Scholar
• Unverzagt , C. 1994 . Synthese eines verzweigten heptasaccharids durch regioselektive glycosylierungen . Angew. Chem. , 106 : 1170 – 1173 .
   Google Scholar
• Dasgupta , F. and Garegg , P. J. 1989 . Synthesis of ethyl and phenyl 1-thio-1,2-trans-D-glycopyranosides from the corresponding per-O-acetylated glycopyranoses having a 1,2-trans-configuration using anhydrous ferric chloride as a promoter . Acta. Chem. Scand. , 43 : 471 – 475 .
   Google Scholar