Synthesis of sugar nucleotides by application of phosphoramidites

Journal of Organic Chemistry

Volumn 73, Issue 23, 2008, Pages 9458-9460

  Gold, Henrik ^a   Van Delft, Pieter ^a   Meeuwenoord, Nico ^a   Codée, Jeroen D C ^a   Filippov, Dmitri V ^a   Eggink, Gerrit ^b   Overkleeft, Herman S ^a   Van Der Marel, Gijs A ^a  

^a LEIDEN UNIVERSITY   (Netherlands)

^b WAGENINGEN UNIVERSITY   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL REACTIONS; NUCLEIC ACIDS; SUGAR (SUCROSE); SYNTHESIS (CHEMICAL);

ACETYLGLUCOSAMINE; CHEMICAL EQUATIONS; GOOD YIELDS; IN-SITU; ONE POTS; PHOSPHORAMIDITE; PHOSPHORAMIDITES; SUGAR NUCLEOTIDES; SUGAR PHOSPHATES; SYNTHESIS OF;

SUGARS;

GLUCOSAMINE DERIVATIVE; PHOSPHORAMIDOUS ACID; SUGAR NUCLEOTIDE; URIDINE DIPHOSPHATE N ACETYLGLUCOSAMINE; CARBOHYDRATE; N ACETYLGLUCOSAMINE; NUCLEOSIDE; NUCLEOTIDE; ORGANOPHOSPHORUS COMPOUND; PHOSPHATE; PHOSPHITE; URIDINE DIPHOSPHATE;

ARTICLE; BIOSYNTHESIS; CARBOHYDRATE SYNTHESIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; ONE POT SYNTHESIS; OXIDATION; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION; CHEMICAL MODEL; CHEMISTRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ORGANIC CHEMISTRY; PROCEDURES;

ACETYLGLUCOSAMINE; CARBOHYDRATES; CHEMISTRY, ORGANIC; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, CHEMICAL; NUCLEOSIDES; NUCLEOTIDES; ORGANOPHOSPHORUS COMPOUNDS; PHOSPHATES; PHOSPHITES; URIDINE DIPHOSPHATE;

EID: 57449089356     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo802021t     Document Type: Article

References (34)

1. Watkins, W. Carb. Res. 1986, 149, 1.
2. (a) Coutinho, P. M.; Deleury, E.; Davies, G. J.; Henrissat, B. J. Mol. Biol. 2003, 328, 307.
3. (b) The glycosyltransferase family server at: http://www.cazy.org/fam/ acc_GT (accessed Aug 25, 2008).
4. Ohtsubo, K.; Marth, J. D. Cell. 2006, 126, 855.
5. Hancock, S. M.; Vaughan, M. D.; Withers, S. G. Curr. Opin. Chem. Biol. 2006, 10, 509.
6. Prescher, J. A.; Bertozzi, C. R. Cell. 2006, 126, 851.
7. DeAngelis, P. L. Cell. Mol. Life Sci. 1999, 56, 670.
8. Danac, R.; Ball, L.; Gurr, S. J.; Fairbanks, A. J. Carb. Res 2008, 343, 1012.
9. (a) Arlt, M.; Hindsgaul, O. J. Org. Chem. 1995, 60, 14.
10. (b) Timmons, S. C.; Jakeman, D. L. Org. Lett. 2007, 9, 1227.
11. (c) Uchiyama, T.; Hindsgaul, O. J. Carb. Chem. 1998, 17, 1181.
12. (d) Ernst, C.; Klaffke, W. J. Org. Chem. 2003, 68, 5780.
13. In a procedure reported by Hannessian et al. unprotected glycosyl donors (MOP glycosides) were used in the reaction with free UD: (e) Hanessian, S.; Lu, P.-P.; Ishida, H. J. Am. Chem. Soc. 1998, 120, 13296.
14. (a) Moffatt, J. G.; Khorana, H. G. J. Am. Chem. Soc. 1958, 80, 3756.
15. (b) Roseman, S.; Distler, J. J.; Moffatt, J. G.; Khorana, H. G. J. Am. Chem. Soc. 1961, 83, 659.
16. (c) Freel Meyers, C. L.; Borch, R. F. Org. Lett. 2001, 23, 3765.
17. (d) Ohkubo, A.; Aoki, K.; Seio, K.; Sekine, M. Tetrahedron Lett. 2004, 45, 979.
18. (e) Marlow, A. L.; Kiessling, L. L. Org. Lett. 2001, 3, 2517.
19. (f) Timmons, S. C.; Jakeman, D. L. Carb. Res. 2008, 343, 865.
20. (g) Yamazaki, T.; Warren, C. D.; Herscovics, A.; Jeanloz, R. W. Can. J. Chem. 1981, 59, 2247.
21. (h) Nunez, H. A.; O'Connor, J. V.; Rosevear, P. R.; Barker, R. Can. J. Chem. 1981, 59, 2086.
22. (i) Imperiali, B.; Zimmerman, J. W. Tetrahedron Lett. 1990, 31, 6485.
23. (a) Wittmann, V.; Wong, C.-H. J. Org. Chem. 1997, 62, 2144.
24. (b) Busca, P.; Piller, V.; Piller, F.; Martin, O. R. Bioorg. Med. Chem. Lett. 2003, 13, 1853.
25. (c) Muller, T.; Danac, R.; Ball, L.; Gurr, S. J.; Fairbanks, A. J. Tetrahedron Asymmetry 2007, 18, 1299.
26. (d) Danac, R.; Ball, L.; Gurr, S. J.; Fairbanks, A. J. Carb. Res. 2008, 343, 1012.
27. (e) Chang, R.; Moquist, P.; Finney, N. S. Carb. Res. 2004, 339, 1531.
28. (f) Stolz, F; Blume, A.; Hinderlich, S.; Reutter, W.; Schmidt, R. R. Eur. J. Org. Chem. 2004, 3304.
29. Wendicke, S.; Warnecke, S.; Meier, C. Angew. Chem., Int. Ed. 2008, 47, 1500.
30. Caruthers, M. H.; Barone, A. D.; Beaucage, S. L.; Dodds, D. R.; Fisher, E. F.; McBride, L. J.; Matteucci, M.; Stabinsky, Z.; Tang, J-Y. Methods Enz. 1987, 154, 287.
31. Yeager, A. D.; Finney, N. S. J. Org. Chem. 2005, 70, 1269.
32. Filippov, D.; Kuyl-Yeheskiely, E.; van der Marel, G. A.; Tesser, G. I.; van Boom, J. H. Tetrahedron Lett. 1998, 39, 3597.
33. Vargeese, C.; Carter, J.; Yegge, J.; Krivjansky, S.; Settle, A.; Kopp, E.; Peterson, K.; Pieken, W. Nucl. Acid. Res. 1998, 26, 1046.
34. Anhydrous conditions were used to prevent possible hydrolysis of the labile phosphite-phosphate anhydride 11.