Transglycosylation activity of Bacillus 1,3-1,4-β-D-glucan 4-glucanohydrolases. Enzymic synthesis of alternate 1,3,-1,4-β-D-glucooligosaccharides

Abstract

The title enzyme from Bacillus licheniformis has been shown to catalyse the effective autocondensation of β-laminaribiosyl fluoride, and lead to alternate 1,3-1,4-β-D-glucotetraose and -glucohexaose products. The transglycosylation using the same donor and methyl β-laminaribioside as acceptor leads to the methyl 4-O-β-laminaribiosyl-β- laminaribioside in 40% overall yield.

References

1. F. W. Parrish, A. S. Perlin and E. T. Reese, Can. J. Chem., 1960, 38, 2094.
2. M. A. Anderson and B. A. Stone, FEBS Lett., 1975, 52, 202.
3. C. Malet, J. Jimenez-Barbero, M. Bernabé, C. Brosa and A. Planas, Biochem. J., 1993, 256, 753.
4. A. Planas, M. Juncosa, J. Lloberas and E. Querol, FEBS Lett., 1992, 308, 141.
5. M. Juncosa, J. Pons, T. Dot, E. Querol and A. Planas, J. Biol. Chem., 1994, 269, 14 530.
6. C. Malet, J. L. Viladot, A. Ochoa, B. Gállego, C. Brosa and A. Planas, Carbohydr. Res., 1995, 274, 285.
7. V. Moreau, J. L. Viladot, E. Samain, A. Planas and H. Driguez, Bioorg. Med. Chem., 1996, 4, 1849.
8. S. Kobayashi, K. Kashiwa, T. Kawasaki and S. I. Shoda, J. Am. Chem. Soc., 1991, 113, 3079.
9. S. Shoda, T. Kawasaki, K. Obata and S. Kobayashi, Carbohydr. Res., 1993, 249, 127.
10. O. Karthaus, S. Shoda, H. Takano, K. Obata and S. Kobayashi, J. Chem. Soc., Perkin Trans. 1, 1994, 1851.
11. V. Moreau and H. Driguez, J. Chem. Soc., Perkin Trans. 1, 1996, 525.
12. S. Armand, S. Drouillard, M. Schulein, B. Henrissat and H. Driguez, J. Biol. Chem., 1997, 272, 2709.
13. G. Okada, D. S. Genghof and E. J. Hehre, Carbohydr. Res., 1979, 71, 287.
14. S. Kobayashi, J. Shimada, K. Kashiwa and S. I. Koda, Macromolecules, 1992, 25, 3237.
15. N. Payre, S. Cottaz and H. Driguez, Angew. Chem., Int. Ed. Engl., 1995, 34, 1239.
16. A. Thompson and M. L. Wolfrom, Methods Carbohydr. Chem., 1963, 2, 215.
17. D. Dess, H. P. Kleine, D. V. Weinberg, R. J. Kaufman and R. S. Sidhu, Synthesis, 1981, 883.
18. A. Planas, M. Juncosa, A. Cayetano and E. Querol, Appl. Microbiol. Biotechnol., 1992, 37, 583.
19. A. Planas and C. Malet, in Carbohydrate Bioengineering, ed. S. B. Petersen, B. Svensson and S. Pedersen, Elsevier, Amsterdam, 1995, p. 85.
20. K. Takeo, Carbohydr. Res., 1979, 77, 245.