2-Allylphenyl glycosides as glycosyl donors for sugar coupling

Carbohydrate Research

Volumn 352, Issue , 2012, Pages 197-201

  Luo, Shun Yuan ^a   Tripathi, Ashish ^b   Zulueta, Medel Manuel L ^b   Hung, Shang Cheng ^b,c  

^a NATIONAL TSING HUA UNIVERSITY   (Taiwan)

^b GENOMICS RESEARCH CENTER   (Taiwan)

^c NATIONAL CHIAO TUNG UNIVERSITY   (Taiwan)

Author keywords

2 Allylphenyl glycoside; Bleomycin; d Mannose; Glycosylation; Stereoselectivity

Indexed keywords

BLEOMYCIN; BLEOMYCINS; D-MANNOSE; EFFICIENT SYNTHESIS; GLYCOSYL DONORS; GLYCOSYLATIONS;

GLYCOSYLATION; ORGANIC COMPOUNDS; STEREOSELECTIVITY; SYNTHESIS (CHEMICAL);

SUGARS;

2 ALLYLPHENYLGLYCOSIDE; ALCOHOL; BLEOMYCIN; DISACCHARIDE; GLYCOSIDE; MANNOSIDE; SUGAR; UNCLASSIFIED DRUG;

ARTICLE; CARBOHYDRATE SYNTHESIS; GLYCOSYLATION; PRIORITY JOURNAL; REACTION OPTIMIZATION;

BLEOMYCIN; CATALYSIS; GLYCOSIDES; GLYCOSYLATION;

EID: 84859491832     PISSN: 00086215     EISSN: 1873426X     Source Type: Journal    
DOI: 10.1016/j.carres.2012.01.022     Document Type: Article

References (28)

1. A. Varki, R.D. Cummings, J.D. Esko, H.H. Freeze, P. Stanley, C.R. Bertozzi, G.W. Hart, and M.E. Etzler Essentials of Glycobiology 2nd ed. 2009 Cold Spring Harbor Laboratory Press New York
2. B.D. Shur, C. Rodeheffer, M.A. Ensslin, R. Lyng, and A. Raymond Mol. Cell. Endocrinol. 250 2006 137 148
3. G.A. Rabinovich, and M.A. Toscano Nat. Rev. Immunol. 9 2009 338 352
4. R.S. Haltiwanger, and J.B. Lowe Annu. Rev. Biochem. 73 2004 491 537
5. N. Sharon Biochim. Biophys. Acta 1760 2006 527 537
6. R.J. Sugrue R.J. Sugrue, Glycovirology Protocols 2007 Humana Press Totawa, New Jersey 1 13
7. R.I. Hollingsworth, and G. Wang Chem. Rev. 100 2000 4267 4282
8. M. Diéguez, O. Pàmies, and C. Claver Chem. Rev. 104 2004 3189 3216
9. D.E. Levy, and P. Fügedi The Organic Chemistry of Sugars 2006 Taylor and Francis Group Boca Raton, FL
10. W. Koenig, and E. Knorr Ber. Dtsch. Chem. Ges. 34 1901 957 981
11. A.V. Demchenko Handbook of Chemical Glycosylation 2008 Wiley-VCH Weinheim
12. K. Toshima, and K. Sasaki J.P. Kamerling, Comprehensive Glycoscience. From Chemistry to Systems Biology 2007 Elsevier Amsterdam 261 311
13. D.R. Mootoo, V. Date, and B. Fraser-Reid J. Am. Chem. Soc. 110 1988 2662
14. B. Fraser-Reid, U.E. Udodong, Z. Wu, H. Ottoson, J.R. Meritt, C.S. Rao, C. Roberts, and R. Madsen Synlett 1992 927 942
15. P.J. Garegg Adv. Carbohydr. Chem. Biochem. 52 1997 179 205
16. A.V. Demchenko, P. Pornsuriyasak, C. De Meo, and N.N. Malysheva Angew. Chem., Int. Ed. 43 2004 3069 3072
17. B. Fraser-Reid, and R. Madsen S. Hanessian, Preparative Carbohydrate Chemistry 1997 Marcel Dekker New York 339 356
18. J.-C. Lee, G.-R. Pan, S.S. Kulkarni, S.-Y. Luo, C.-C. Liao, and S.-C. Hung Tetrahedron Lett. 47 2006 1621 1624
19. M. Fortin, J. Kaplan, K. Pham, S. Kirk, and R.B. Andrade Org. Lett. 11 2009 3594 3597
20. C.-A. Tai, S.S. Kulkarni, and S.-C. Hung J. Org. Chem. 68 2003 8719 8722
21. M.G. Paulick, and C.R. Bertozzi Biochemistry 47 2008 6991 7000
22. R.E.B. Lee, W. Li, D. Chatterjee, and R.E. Lee Glycobiology 15 2005 139 151
23. M. Sugiyama, and T. Kumagai J. Biosci. Bioeng. 93 2002 105 116
24. S.M. Hecht J. Nat. Prod. 63 2000 158 168
25. C.A. Claussen, and E.C. Long Chem. Rev. 99 1999 2797 2816
26. J.-C. Lee, X.-A. Lu, S.S. Kulkarni, Y.-S. Wen, and S.-C. Hung J. Am. Chem. Soc. 126 2004 476 477
27. T. Takita, Y. Umezawa, S.-I. Saito, H. Morishima, H. Naganawa, H. Umezawa, T. Tsuchiya, T. Miyake, S. Kageyama, S. Umezawa, Y. Muraoka, M. Suzuki, M. Otsuka, M. Narita, S. Kobayashi, and M. Ohno Tetrahedron Lett. 23 1982 521 524
28. T. Tsuchiya, T. Miyake, S. Kageyama, S. Umezawa, H. Umezawa, and T. Takita Tetrahedron Lett. 22 1981 1413 1416