SYNTHESIS AND APPLICATION OF SPACER-MODIFIED L-FUCOSE ANALOGUESCitation[1]

REFERENCES

• Brackhagen , M and Vogel , C. Abstract B-389 . 20th International Carbohydrate Symposium . August 27-September 1 2000 , Hamburg, Germany. Edited by: Thiem , J. Hamburg : LCI Publisher GmbH . Part V of the series “L-Fucose Derivatives”, for part IV see ref. 3
   Google Scholar
• Vogel , C. , Bergemann , C. , Ott , A.-J. , Lindhorst , T. K. , Thiem , J. , Dahlhoff , W. V. , Hällgren , C. , Palcic , M. M. and Hindsgaul , O. 1997 . Synthesis of Carbon-Backbone-Elongated GDP-L-Fucose Derivatives as Substrates for Fucosyltransferase-Catalysed Reactions . Liebigs Ann./Recueil , : 601 – 612 .
   Google Scholar
• Brackhagen , M , Boye , H. and Vogel , C. 2001 . Synthesis of (6-2H)- and 6-Deoxy-6-fluoro-L-galactose Derivatives . J. Carbohydr. Chem. , 20 : 31 – 43 .
   Web of Science ®Google Scholar
• Sheehan , J. C. and Ledis , S. L. 1973 . Total Synthesis of Monocyclic Peptide Lactone Antibiotic, Etamycin . J. Am. Chem. Soc. , 95 : 875 – 879 .
   PubMedGoogle Scholar
• König , W. and Geiger , R. 1970 . Eine neue Methode zur Synthese von Peptiden: Aktivierung der Carboxylgruppe mit Dicyclohexylcarbodiimid unter Zusatz von 1-Hydroxy-benzotriazolen . Chem. Ber. , 103 : 788 – 798 .
   PubMedGoogle Scholar
• Vogel , C. , Jeschke , U. , Kramer , S. and Ott , A.-J. 1997 . Synthesis of n-(D-Galacturonoyl) Amino Acids and Dipeptides . Liebigs Ann./ Recueil , : 737 – 743 .
   Google Scholar
• Hällgren , C. and Hindsgaul , O. 1995 . An Aminated GDP-Fucose Analog Useful in the Fucosyltransferase Catalyzed Addition of Biological Probes onto Oligosaccharide Chains . J. Carbohydr. Chem. , 14 : 453 – 464 .
   Web of Science ®Google Scholar
• Ishihara , H and Heath , E. C. 1968 . The Metabolism of L-Fucose: The Biosynthesis of Guanosine Diphosphate L-Fucose in Porcine Liver . J. Biol. Chem. , 243 : 1110 – 1115 .
   Google Scholar
• Roseman , S , Distler , J. J. , Moffat , J. G. and Khorana , H. G. 1961 . Nucleoside Polyphosphates. XI. An Improved General Method for the Synthesis of Nucleotide Coenzymes. Synthesis of Uridine-5′, Cytidine-5′ and Guanosine-5′ Diphosphate Derivatives . J. Am. Chem. Soc. , 83 : 659 – 663 .
   Google Scholar
• Jain , R. K. and Matta , K. L. 1990 . Synthesis of the Sodium Salts of Methyl 2-O-α-L-fucopyranosyl-α-L-fucopyranoside 3- and 4-Sulfate . Carbohydr. Res. , 208 : 51 – 58 .
   Google Scholar
• Uchiyama , T , Uchiyama , O. and Hindsgaul , O. 1996 . Per-O-trimethylsilyl-α-L-fucopyranosyl Iodide: A Novel Glycosylating Agent for Terminal α-L-Fucosylation . Synlett , : 499 – 501 .
   Google Scholar
• Fernandez-Mayoralas , A. and Martin-Lomas , M. 1986 . Synthesis of 3- and 2′-Fucosyllactose and 3,2′-Difucosyllactose from Partially Benzylated Lactose Derivatives . Carbohydr. Res. , 154 : 93 – 101 .
   Web of Science ®Google Scholar
• Lemieux , R. U. and Morgan , A. R. 1965 . The Synthesis of β-D-Glucopyranosyl 2-Deoxy-α-D-arabino-hexopyranoside . Can. J. Chem. , 43 : 2190 – 2198 .
   Web of Science ®Google Scholar
• Zegelaar-Jaarsveld , K. , van der Marel , G. A. and van Boom , J. H. 1992 . Iodonium Ion Assisted Synthesis of a Common Inner Core Trisaccharide Fragment Corresponding to the Cell-Wall Phenolic Glycolipid of Mycobacterium Kansasii . Tetrahedron , 48 : 10133 – 10148 .
   Google Scholar
• Ravenscroft , M. , Roberts , R. M.G. and Tillett , J. G. 1982 . The Reaction of Some Cyclic and Open-Chain Disulphides with Methyl Trifluoromethanesulphonate . J. Chem. Soc., Perkin Trans. 2 , : 1569 – 1572 .
   Google Scholar
• Fügedi , P. , Garegg , P. J. , Lönn , H. and Norberg , T. 1987 . Thioglycosides as Glycosylating Agents in Oligosaccharide Synthesis . Glycoconjugate J. , 4 : 97 – 108 .
   Web of Science ®Google Scholar
• Fernandez-Mayoralas , A. , Martin-Lomas , M. and Villanueva , D. 1985 . 4-O-β-D-Galactopyranosyl-3-O-methyl-D-glucose: A New Synthesis and Application to the Evaluation of Intestinal Lactase . Carbohydr. Res. , 140 : 81 – 91 .
   Google Scholar
• Abbas , S. A. , Barlow , J. J. and Matta , K. L. 1981 . Synthesis of O-α-L-Fucopyranosyl-(1→2)-O-β-D-galactopyranosyl-(1→4)-D-glucopyranose (2′-O-α-L-Fucopyranosyllactose) . Carbohydr. Res. , 88 : 51 – 60 .
   Web of Science ®Google Scholar
• Hough , L. , Richardson , A. C. and Thelwall , L. A.W. 1979 . Reaction of Lactose with 2,2-Dimethoxypropane: A Tetra-Acetal of Novel Structure . Carbohydr. Res. , 75 : C11 – C12 .
   Google Scholar
• Barili , P. L. , Catelani , G. , D'Andrea , F. , Rensis , F. D. and Falcini , P. 1997 . Improved Preparation of 2,3:5,6:3′,4′-Tri-O-Isopropylidenelactose Dimethyl Acetal and Its 6-O-(1-Methoxy-1-methylethyl) Derivative . Carbohydr. Res. , 298 : 75 – 84 .
   Web of Science ®Google Scholar
• Izumi , M. , Tsuruta , O. , Harayama , S. and Hashimoto , H. 1997 . Synthesis of 5-Thio-L-fucose-Containing Disaccharides as Sequence-Specific Inhibitors, and 2′-Fucosyllactose, as a Substrate of α-L-Fucosidases . J. Org. Chem. , 62 : 992 – 998 .
   Web of Science ®Google Scholar
• Kunz , C. Germany : Justus-Liebig University of Gieβen . unpublished results
   Google Scholar
• Kunz , C. , Rudloff , S. , Hintelmann , A. , Pohlentz , G. and Egge , H. 1996 . High-pH Anion-Exchange Chromatography with Pulsed Amperometric Detection and Molar Response Factors of Human Milk Oligosaccharides . J. Chromatogr. B , 685 : 211 – 221 .
   PubMed Web of Science ®Google Scholar
• Kunz , C. and Rudloff , S. 1993 . Biological Functions of Oligosaccharides in Human Milk . Acta Pædiatr. , 82 : 903 – 912 .
   PubMed Web of Science ®Google Scholar
• Perrin , D. D. and Armarego , W. L.F. 1988 . Purification of Laboratory Chemicals , 3rd Ed. Oxford : Pergamon Press .
   Google Scholar