Enzymatic synthesis of complex glycosaminotrioses and study of their molecular recognition by hevein domains

Organic and Biomolecular Chemistry

Volumn 2, Issue 14, 2004, Pages 1987-1994

  Aboitiz, Nuria ^a   Cañada, F Javier ^a   Hušáková, Lucie ^b   Kuzma, Marek ^b   Křen, Vladimír ^b   Jiménez Barbero, Jesús ^a  

^a CENTRO DE INVESTIGACIONES BIOLÓGICAS   (Spain)

^b INSTITUTE OF MICROBIOLOGY   (Czech Republic)

Author keywords

[No Author keywords available]

Indexed keywords

ENZYMES; GELS; HYDROGEN BONDS; MONOMERS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SOLVENTS; SYNTHESIS (CHEMICAL); X RAY CRYSTALLOGRAPHY;

EPIMERIZATION; FUNGAL CELLS; GEL FILTRATION; MOLECULAR MODELING;

ORGANIC POLYMERS;

ASPERGILLUS; ASPERGILLUS ORYZAE; HEVEA BRASILIENSIS;

ANTIMICROBIAL CATIONIC PEPTIDE; BETA N ACETYLHEXOSAMINIDASE; CHITIN; HEVEIN; N ACETYLGLUCOSAMINE; OLIGOSACCHARIDE; PLANT LECTIN; TRISACCHARIDE;

ARTICLE; ASPERGILLUS ORYZAE; CARBOHYDRATE ANALYSIS; CHEMISTRY; ENZYMOLOGY; MOLECULAR GENETICS; PHYSIOLOGY; PROTEIN BINDING; PROTEIN CONFORMATION; PROTEIN TERTIARY STRUCTURE; SYNTHESIS;

ACETYLGLUCOSAMINE; ANTIMICROBIAL CATIONIC PEPTIDES; ASPERGILLUS ORYZAE; BETA-N-ACETYLHEXOSAMINIDASE; CARBOHYDRATE SEQUENCE; CHITIN; MOLECULAR SEQUENCE DATA; OLIGOSACCHARIDES; PLANT LECTINS; PROTEIN BINDING; PROTEIN CONFORMATION; PROTEIN STRUCTURE, TERTIARY; TRISACCHARIDES;

EID: 3843090507     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b401037j     Document Type: Article

References (53)

1. Glycosciences, Status and Perspectives, ed. H. J. Gabius and S. Gabius, Chapman & Hall, London-Weinheim, 1997.
2. M. R. Wormald, A. J. Petrescu, Y. L. Pao, A. Glithero, T. Elliott and R. A. Dwek, Chem. Rev., 2002, 102, 371-386.
3. For a current view of the state of the art of carbohydrate NMR, see J. Jiménez-Barbero and T. Peters, NMR Spectroscopy of Glycoconjugates., Wiley-VCH, Weinheim, 2002.
4. (a) J. H. Naismith and R. A. Field, J. Biol. Chem., 1996, 271, 972-976;
5. (b) J. Bouckaert, T. W. Hamelryck and L. Wyns and R. Loris, J. Biol. Chem., 1999, 274, 29188-29195;
6. (c) W. I. Weis and K. Drickamer, Annu. Rev. Biochem., 1996, 65, 441-473.
7. H. C. Siebert, R. Adar, R. Arango, M. Burchert, H. Kaltner, G. Kayser, E. Tajkhorshid, C. W. Lieth, R. Kaptein, N. Sharon, J. F. G. Vliegenthart and H. J. Gabius, Eur. J. Biochem., 1997, 249, 27-38.
8. H. C. Siebert, C. W. von der Lieth, R. Kaptein, J. J. Beintema, K. Dijkstra, N. van Nuland, U. M. S. Soedjanaatmadja, A. Rice, J. F. G. Vliegenthart, C. S. Wright and H. J. Gabius, Proteins: Struct., Funct., Genet., 1997, 28, 268-284.
9. W. J. Peumanns and E. J. M. van Damme, Histochem. J., 1995, 27(4), 253-271.
10. (a) N. V. Raikhel, H. I. Lee and W. F. Broekaert, Annu. Rev. Plant. Physiol., 1993, 44, 591-615;
11. (b) J. J. Beintema, FEBS Lett., 1994, 350, 159-163.
12. (a) J. Martins, D. Maes, R. Loris, H. A. M. Pepermans, L. Wyns, R. Willen and P. Verheyden, J. Mol. Biol., 1996, 258, 322-333;
13. (b) R. T. Lee, H. J. Gabius and Y. C. Lee, Glycoconjugate J., 1998, 15, 649-655.
14. (a) C. S. Wright, J. Mol. Biol., 1984, 178, 91-104;
15. (b) C. S. Wright, J. Mol. Biol., 1990, 215, 635-51;
16. (c) C. S. Wright, J. Biol. Chem., 1992, 267, 14345-14352.
17. A. Rodríguez, M. Tablero, B. Barragan, P. Lara, M. Rangel, B. Arreguin, L. Possani and M. Soriano-Garcia, J. Cryst. Growth, 1986, 76, 710-714.
18. A. Rodríguez-Romero, K. G. Ravichandran and M. Soriano-Garcia, FEBS Lett., 1991, 291, 307-309.
19. (a) J. L. Asensio, F. J. Cañada, M. Bruix, A. Rodriguez-Romero and J. Jiménez-Barbero, Eur. J. Biochem., 1995, 230, 621-633;
20. (b) J. L. Asensio, F. J. Cañada, M. Bruix, C. Gonzalez, N. Khiar, A. Rodríguez-Romero and J. Jiménez-Barbero, Glycobiology, 1998, 8, 569-577.
21. N. H. Andersen, B. Cao, A. Rodríguez-Romero and B. Arreguin, Biochemistry, 1993, 32, 1407-1422.
22. J. L. Asensio, F. J. Canada, H. C. Siebert, J. Laynez, A. Poveda, P. M. Nieto, U. M. Soedjanaamadja, J. J. Beintema, H. J. Gabius and J. Jiménez-Barbero, Chem. Biol., 2000, 7, 529-543.
23. (a) P. Sedmera, V. Prikrylová, K. Bezouška, E. Rajnochová, J. Thiem and V. Kren, J. Carb. Chem., 1998, 17, 1351-1357;
24. (b) C. A. Lobry de Bruyn and W. A. van Ekenstein, Rec. Trav. Chim. Pays-Bas., 1899, 18, 147-149.
25. L. Hušáková, E. Herkommerová- Rajnochová, T. Semenuk, M. Kuzma, J. Rauvolfová, V. Prikrylová, R. Ettrich, O. Plihal, K. Bezouška and V. Kren, Adv. Synth. Catal., 2003, 345, 735-742.
26. V. Kren and J. Thiem, Chem. Soc. Rev., 1997, 26, 463-474.
27. S. Singh, J. Packwood, C. J. Samuel, P. Critchley and D. H. G. Crout, Carbohydr. Res., 1995, 279, 293-305.
28. N. L. Allinger, Y. H. Yuh and J. H. Lu, J. Am. Chem. Soc., 1989, 111, 8551-8566.
29. F. Mohamadi, N. G. J. Richards, W. C. Guida, R. Liskamp, C. Caufield, G. Chang, T. Hendrickson and W. C. Still, J. Comput. Chem., 1990, 11, 440-467.
30. J. F. Espinosa, J. L. Asensio and M. Bruix and J. Jiménez-Barbero, An. Quim., 1996, 92, 320-324.
31. For a discussion on the application of molecular mechanics force fields to sugar molecules, see S. Perez, A. Imberty, S. Engelsen, J. Gruza, K. Mazeau, J. Jiménez-Barbero, A. Poveda, J. F. Espinosa, B. P. van Eyck, G. Johnson, A. D. French, M. Louise, C. E. Kouwijzer, P. D. J. Grootenuis, A. Bernardi, L. Raimondi, H. Senderowitz, V. Durier, G. Vergoten and K. Rasmussen, Carbohydr. Res., 1998, 314, 141-155.
32. W. C. Still, A. Tempczyk, R. C. Hawley and T. Hendrickson, J. Am. Chem. Soc., 1990, 112, 6127-6128.
33. L. M. Mikkelsen, M. J. Hernáiz, M. Martín-Pastor, T. Skrydstrup and J. Jiménez-Barbero, J. Am. Chem. Soc., 2002, 124, 14940-14951.
34. D. A. Cumming and J. P. Carver, Biochemistry, 1987, 26, 6664-6676.
35. J. L. Asensio, F. J. Cañada and J. Jiménez-Barbero, Eur. J. Biochem., 1995, 233, 618-630.
36. J. L. Asensio, A. Gracia, M. T. Murillo, A. Fernández-Mayoralas, F. J. Cañada, C. R. Johnson and J. Jiménez-Barbero, J. Am. Chem. Soc., 1999, 121, 11318-11329.
37. (a) R. U. Lemieux, Acc. Chem. Res., 1996, 29, 373-380;
38. (b) J. P. Carver, S. W. Michnick, A. Imberty and D. A. Gumming, Ciba Found. Symp., 1991, 158, 6-26;
39. (c) M. S. Searle and D. H. Williams, J. Am. Chem. Soc., 1992, 114, 10690-10697;
40. (d) H. J. Gabius, Pharm. Res., 1998, 15, 23-30.
41. (a) K. A. Kronis and J. P. Carver, Biochemistry, 1985, 24, 834-840;
42. (b) K. A. Kronis and J. P. Carver, Biochemistry, 1985, 24, 826-833.
43. (a) D. A. Pearlman, D. A. Case, J. W. Caldwell, W. S. Ross, T. E. Cheatham, S. DeBolt, D. Ferguson, G. Siebal and P. A. Kollmann, Comput. Phys. Commun., 1995, 91, 1-41;
44. (b) D. A. Pearlman and P. A. Kollmann, J. Mol. Biol., 1991, 220, 457-479.
45. D. Uhrín and P. N. Barlow, J. Magn. Reson., 1997, 126, 248-255.
46. C. E. A. F. Schafmeister, W. S. Ross and V. Romanovski, LEAP, 1995, University of California, San Francisco.
47. K. Bezouška, G. Vlahas, O. Horváth, G. Jinochová, A. Fišerová, R. Giorda, W. H. Chambers, T. Feizi and M. Pospišil, J. Biol. Chem., 1994, 269, 16945-16952.
48. (a) P. Krist, E. Herkommerová-Rajnochová, J. Rauvolfová, T. Semenuk, P. Vavrušková, J. Pavlícek, K. Bezouška, L. Petruš and V. Kren, Biochem. Biophys. Res. Commun., 2001, 287(1), 11-20;
49. (b) K. Bezouška, J. Sklenár, J. Dvoráková, V. Havlícek, M. Pospíšil, J. Thiem and V. Kren, Biochem. Biophys. Res. Commun., 1997, 238, 149-153.
50. Z. Hunková, V. Kren, M. Šcigelová, L. Weignerová, O. Scheel and J. Thiem, Biotechnol. Lett., 1996, 18, 725-730.
51. L. Weignerová, P. Vavrušková, A. Pišvejcová, J. Thiem and V. Kren, Carbohydr. Res., 2003, 338, 1003-1008.
52. Bezouška and V. Kren, DDBJ/EMBL/GeneBank databases under the accession No. AY091636.
53. K. Bock and Ch. Pedersen, J. Chem. Soc., Perkin Trans. 2, 1974, 293-297.