De novo synthesis and lectin binding studies of unsaturated carba-pyranoses

Organic and Biomolecular Chemistry

Volumn 8, Issue 17, 2010, Pages 3965-3974

  Leermann, Timo ^a   Block, Oliver ^b   Podeschwa, Michael A L ^c   Pfüller, Uwe ^d   Altenbach, Hans Josef ^a  

^a UNIVERSITY OF WUPPERTAL   (Germany)

^b MERCK KGAA   (Germany)

^c SANOFI AVENTIS DEUTSCHLAND GMBH   (Germany)

^d UNIVERSITY MEDICAL CENTER HAMBURG EPPENDORF   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOQUINONES; DE NOVO SYNTHESIS; FLEXIBLE ROUTES; LECTIN BINDING; SURFACE PLASMON RESONANCE SPECTROSCOPY;

CARBOHYDRATES;

SURFACE PLASMON RESONANCE;

CARBASUGAR; LECTIN;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

CARBASUGARS; LECTINS; MOLECULAR STRUCTURE;

EID: 77955494882     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/c003597a     Document Type: Article

References (41)

1. C. W. M. Grant M. W. Peters Biochim. Biophys. Acta, Reviews on Biomembranes 1984 779 403
2. N. Sharon H. Lis Science 1989 246 227
3. A. Varki Glycobiology 1993 3 97
4. N. Sharon H. Lis Sci. Am. 1993 268 82
5. R. Eifler, K. Pfüller, W. Göckeritz and U. Pfüller, Lectins: Biology, Biochemistry, Clinical Biochemistry, ed., J. Basu, M. Kundu, and, P. Chakrabarti, Wiley Eastern, New Delhi, India, 1994, vol. 9, p. 144
6. U. Pfüller, Chemical Constituents of European Misteltoe (Viscum Album L.), Isolation and Characterization of the Main Relevant Ingredients: Lectins, Viscotoxins, Oligo-/polysaccharides, Flavonoides in, Misteltoe: The Genus Viscum, ed., A. Büssing, Harwood Academic Publishers, Amsterdam, 2000, 101
7. H. Lis N. Sharon Chem. Rev. 1998 98 637
8. T. Suami S. Ogawa Adv. Carbohydr. Chem. Biochem. 1990 48 21
9. Y. Kobayashi, Carbasugars in, Glycoscience: Chemistry and Chemical Biology Vol. III, ed., B. O. Fraser-Reid, K. Tatsuta, and, J. Thiem, Springer-Verlag, Berlin, Heidelberg, New York, 2001
10. M. Sollogoub and P. Sinay, From Sugars to Carbasugars in, The Organic Chemistry of Sugars, ed. D. E. Levy and P. Fügedi, CRC Press, Boca Raton, 2006, ch. 8
11. T. Suami Pure Appl. Chem. 1987 59 1509
12. S. Ogawa, in Carbohydrate Mimics, Concepts and Methods, ed., Y. Chapleur, Wiley-VCH, Weinheim, 1988, 87
13. T. Suami Top. Curr. Chem. 1990 154 257
14. O. Arjona A. M. Gómez J. C. López J. Plumet Chem. Rev. 2007 107 1919
15. J. H. Musser Annu. Rep. Med. Chem. 1992 27 301
16. R. A. Dwek Chem. Rev. 1996 96 683
17. Z. J. Witczak, in Carbohydrates in Drug Design, ed., Z. J. Witczak, and, K. A. Nieforth, Marcel Dekker, New York, 1997
18. A. Isogai S. Sakuda J. Nakayama S. Watanabe S. Suzuki Agric. Biol. Chem. 1987 51 2277
19. S. Horii T. Iwasa E. Mizuta Y. Kameda J. Antibiot. 1971 24 59
20. Y. Kameda S. Horii J. Chem. Soc., Chem. Commun. 1972 746
21. Y. Kameda N. Asano M. Yoshikawa M. Takeuchi T. Yamaguchi K. Matsui S. Horii H. Fukase J. Antibiot. 1984 37 1301
22. S. Atsumi K. Umezawa H. Iinuma H. Naganawa H. Nakamura Y. Iitaka T. Takeuchi J. Antibiot. 1990 43 49
23. S. Atsumi H. Iinuma C. Nosaka K. Umezawa J. Antibiot. 1990 43 1579
24. N. Yoshikawa, N. Chiba, T. Mikawa, S. Ueno, K. Harimaya and M. Iwata, JP 0630600, 1994
25. G. Bach S. Breiding-Mack S. Grabley P. Hammann K. Hütter R. Thiericke H. Uhr J. Wink A. Zeeck Liebigs Ann. Chem. 1993 115 241
26. A. Numata M. Isitani T. Yamada K. Minoura E. Matsumura T. Yamori T. Tsuruo Tetrahedron Lett. 1997 38 8215
27. Y. Usami Y. Horibe I. Takaoka H. Ichikawa M. Arimoto Synlett 2006 1598
28. T. Yamada M. Iritani H. Ohishi K. Tanaka K. Minoura M. Doi A. Numata Org. Biomol. Chem. 2007 5 3979
29. Y. Usami K. Suzuki K. Mizuki H. Ichikawa M. Arimoto Org. Biomol. Chem. 2009 7 315
30. S. C. Taneja S. K. Koul P. Pushpangadan K. L. Dhar W. M. Daniewski W. Schilf Phytochemistry 1991 30 871
31. J. L. Koul S. K. Koul S. C. Taneja K. L. Dhar Phytochemistry 1996 41 1097
32. O. Plettenburg S. Adelt G. Vogel H.-J. Altenbach Tetrahedron: Asymmetry 2000 11 1057
33. O. Block G. Klein H.-J. Altenbach J. Org. Chem. 2000 65 716
34. S. Adelt O. Plettenburg G. Dallmann F. P. Ritter S. B. Shears H.-J. Altenbach G. Vogel Bioorg. Med. Chem. Lett. 2001 11 2705
35. M. A. L. Podeschwa O. Plettenburg H.-J. Altenbach Org. Biomol. Chem. 2003 1 1919
36. M. Podeschwa O. Plettenburg J. vom Brocke O. Block S. Adelt H.-J. Altenbach Eur. J. Org. Chem. 2003 1958
37. M. A. L. Podeschwa O. Plettenburg H.-J. Altenbach Eur. J. Org. Chem. 2005 14 3101
38. C. Prévost Compt. Rend. 1933 196 1129
39. R. B. Woodward J. Am. Chem. Soc. 1958 80 209
40. R. Mikesaka R. Wacker R. Arni T. P. Singh A. Mikhailov A. Gabdoulkhakov W. Voelter C. Betzel Acta. Cryst., Section F 2005 61 17
41. N. Chida T. Tanikawa T. Tobe S. Ogawa J. Chem. Soc., Chem. Commun. 1994 1247