Collect. Czech. Chem. Commun. 2003, 68, 801-811
https://doi.org/10.1135/cccc20030801

Synthesis of 4-Nitrophenyl 2-Acetamido-2-deoxy-β-D-mannopyranoside and 4-Nitrophenyl 2-Acetamido-2-deoxy-α-D-mannopyranoside

Pavel Krista, Marek Kuzmab, István F. Pelyvásc, Pavla Simerskáa and Vladimír Křena,*

a Laboratory of Biotransformation, Institute of Microbiology, Academy of Sciences of the Czech Republic, Vídeňská 1083, CZ-142 20 Prague 4, Czech Republic
b Laboratory of Molecular Structure Characterization, Institute of Microbiology, Academy of Sciences of the Czech Republic, Vídeňská 1083, CZ-142 20 Prague 4, Czech Republic
c Research Group of Antibiotics, Hungarian Academy of Sciences, University of Debrecen, P.O. Box 70, H-4010 Debrecen, Hungary

References

1. Gridley J. J., Osborn H. M. I.: J. Chem. Soc., Perkin Trans. 1 2000, 1471. <https://doi.org/10.1039/a909165c>
2. Nilsson M., Norberg T.: J. Chem. Soc., Perkin Trans. 1 1998, 1699. <https://doi.org/10.1039/a709293h>
3. Yokoyama K., Mizuguchi H., Araki Y., Kaya S., Ito E.: J. Bacteriol. 1989, 171, 940. <https://doi.org/10.1128/jb.171.2.940-946.1989>
4. Lee C. J., Banks S. D., Li J. P.: Crit. Rev. Microbiol. 1991, 18, 89. <https://doi.org/10.3109/10408419109113510>
5. Lee C. J., Fraser B. A.: J. Biol. Chem. 1980, 255, 6847.
6. Krist P., Herkommerová-Rajnochová E., Rauvolfová J., Semeňuk T., Vavrušková P., Pavlíček J., Bezouška K., Petruš L., Křen V.: Biochem. Biophys. Res. Commun. 2001, 287, 11. <https://doi.org/10.1006/bbrc.2001.5537>
7. Sedmera P., Přikrylová V., Bezouška K., Rajnochová E., Thiem J., Křen V.: J. Carbohydr. Chem. 1998, 17, 1351. <https://doi.org/10.1080/07328309808002358>
8. Naik R. S., Davidson E. A., Gowda D. C.: J. Biol. Chem. 2000, 275, 24506. <https://doi.org/10.1074/jbc.M002151200>
9. Keppler O. T., Stehling P., Herrmann M., Kayser H., Grunow D., Reutter W., Pawlita M.: J. Biol. Chem. 1995, 270, 1308. <https://doi.org/10.1074/jbc.270.3.1308>
10. Kuan S. F., Byrd J. C., Basbaum C., Kim Y. S.: J. Biol. Chem. 1989, 264, 19271.
11. Bezouška K., Křen V., Kieburg C., Lindhorst T. K.: FEBS Lett. 1998, 426, 243. <https://doi.org/10.1016/S0014-5793(98)00340-8>
12. Yoshimura J., Sakai H., Oda N., Hashimoto H.: Bull. Chem. Soc. Jpn. 1972, 45, 2027. <https://doi.org/10.1246/bcsj.45.2027>
13. Ritchmyer N. K.: Methods Carbohydr. Chem. 1962, 1, 107.
14. Guthrie R. D., Murphy D.: J. Chem. Soc. 1963, 5288. <https://doi.org/10.1039/jr9630005288>
15. Sugawara T., Igarashi K.: Carbohydr. Res. 1988, 172, 195. <https://doi.org/10.1016/S0008-6215(00)90854-1>
16. Litjens R. E. J. N., Leewenburgh M. A., Marel G. A., Boom J. H.: Tetrahedron Lett. 2001, 42, 8693. <https://doi.org/10.1016/S0040-4039(01)01880-9>
17. Paulsen H., Lorentzen P.: Carbohydr. Res. 1984, 133, C1. <https://doi.org/10.1016/0008-6215(84)85195-2>
18. Paulsen H., Lockhoff O.: Chem. Ber. 1981, 114, 3079. <https://doi.org/10.1002/cber.19811140915>
19. Yasukochi Y., Inaba C., Fukase K., Kusumoto S.: Tetrahedron Lett. 1999, 40, 6585. <https://doi.org/10.1016/S0040-4039(99)01279-4>
20. Classon B., Garegg P. J., Oscarson S., Tiden A. K.: Carbohydr. Res. 1991, 216, 187. <https://doi.org/10.1016/0008-6215(92)84161-K>
21. Adachi T., Yamada Y., Inoue I.: Synthesis 1977, 45. <https://doi.org/10.1055/s-1977-24270>
22. De Bruyn A., Anteunis M.: Org. Magn. Reson. 1976, 8, 228. <https://doi.org/10.1002/mrc.1270080416>
23. Bock K., Pedersen Ch.: J. Chem. Soc., Perkin Trans. 2 1974, 293. <https://doi.org/10.1039/p29740000293>