L. Cai et al. / Bioorg. Med. Chem. Lett. 19 (2009) 5433–5435
5435
Table 1
Acknowledgements
Isolated yields for enzymatic 1-phosphorylation reactions
R3
R3
R2
O
R2
O
P. G. Wang acknowledges National Cancer Institute (R01
CA118208), NSF (CHE-0616892) for financial support. W. Guan
acknowledges China Scholarship Council for financial support. Mass
spectra data were collected on a Bruker micrOTOF instrument pro-
vided by a grant from the Ohio BioProducts Innovation Center.
NahK
ATP
HO
HO
OH
O
P
NH
HN
O
R1
R1
O
O
O
O
NH4
2
1-10
Supplementary data
Entry
Substrate structure
1-Phosphorylation yield (%)
Supplementary data associated with this article can be found, in
OH
HO
78a
References and notes
O
1
HO
AcHN
1. Lindahl, U.; Hook, M. Annu. Rev. Biochem. 1978, 47, 385.
2. (a) Carraway, K. L.; Hull, S. R. Glycobiology 1991, 1, 131; (b) Hang, H. C.; Bertozzi,
C. R. Bioorg. Med. Chem. 2005, 13, 5021.
3. Koeller, K. M.; Wong, C.-H. Chem. Rev. 2000, 100, 4465.
4. Piller, F.; Hanlon, M. H.; Hill, R. L. J. Biol. Chem. 1983, 258, 10774.
5. (a) Pastuszak, I.; Drake, R.; Elbein, A. D. J. Biol. Chem. 1996, 271, 20776; (b)
Szumilo, T.; Zeng, Y.; Pastuszak, I.; Drake, R.; Szumilo, H.; Elbein, A. D. J. Biol.
Chem. 1996, 271, 13147.
6. Bourgeaux, V.; Piller, F.; Piller, V. Bioorg. Med. Chem. Lett. 2005, 15, 5459.
7. Bourgeaux, V.; Cadene, M.; Piller, F.; Piller, V. ChemBioChem 2007, 8, 37.
8. Nishimoto, M.; Kitaoka, M. Appl. Environ. Microbiol. 2007, 73, 6444.
9. Cai, L.; Guan, W.; Kitaoka, M.; Shen, J.; Xia, C.; Chen, W.; Wang, P. G. Chem.
Commun. 2009, 2944.
10. Cai, Y.; Ling, C.-C.; Bundle, D. R. J. Org. Chem. 2009, 74, 580.
11. (a) Horton, D.; Rodemeyer, G.; Saeki, H. Carbohydr. Res. 1977, 59, 607; (b) Perry,
M. B.; Daoust, V. Can. J. Chem. 1973, 51, 974.
12. Jiaang, W.-T.; Tseng, P.-H.; Chen, S.-T. Synlett 2000, 797.
13. (a) Kajihara, Y.; Kodama, H.; Endo, T.; Hashimoto, H. Carbohydr. Res. 1998, 306,
361; (b) Jones, G. B.; Lin, Y.; Xiao, Z.; Kappen, L.; Goldberg, I. H. Bioorg. Med.
Chem. 2007, 15, 784.
14. Yonehara, K.; Hashizume, T.; Mori, K.; Ohe, K.; Uemura, S. J. Org. Chem. 1999, 64,
9374.
15. Clinch, K.; Evans, G. B.; Furneaux, R. H.; Rendle, P. M.; Rhodes, P. L.; Roberton, A.
M.; Rosendale, D. I.; Tyler, P. C.; Wright, D. P. Carbohydr. Res. 2002, 337, 1095.
16. Filice, M.; Palomo, J. M.; Bonomi, P.; Bavaro, T.; Fernandez-Lafuente, R.; Guisan,
J. M.; Terreni, M. Tetrahedron 2008, 64, 9286.
17. Lin, F. L.; van Halbeek, H.; Bertozzi, C. R. Carbohydr. Res. 2007, 342, 2014.
18. Berkin, A.; Szarek, M. A.; Plenkiewicz, J.; Szarek, W. A.; Kisilevsky, R. Carbohydr.
Res. 2000, 325, 30.
OH
OH
HO
HO
O
2
3
4
85a
86a
77a
NH
OH
OH
OH
O
Et
OH
HO
HO
O
NH
O
Pr
OH
HO
HO
O
NH
O
Ph
OH
HO
HO
O
19. NMR data for the 1-phosphate derivatives of compound 2, 3, 7 and 9: (a)
Lazarevic, D.; Thiem, J. Carbohydr. Res. 2002, 337, 2187; (b) Illarionov, P. A.;
Torgov, V. I.; Hancock, I. I.; Shibaev, V. N. Russ. Chem. Bull. 2001, 50, 1303; (c)
Srivastava, G.; Alton, G.; Hindsgaul, O. Carbohydr. Res. 1990, 207, 259.
5
65a
NH
OH
O
N3
N3
HO
HO
HO
6
7
8
9
42a
37a
73a
70a
<5b
O
AcHN
OH
OH
O
HO
AcHN
OH
O
N3
HO
AcHN
OH
O
OH
OH
OH
HO
AcHN
OH
O
HO
HO
10
HO
a
Isolated yield from silica gel column chromatography.
Detected by TLC.
b