Endo-β-N-acetylglucosaminidase-catalyzed polymerization of β-Glcp-(1→4)-GlcpNAc oxazoline: a revisit to enzymatic transglycosylation

Carbohydrate Research

Volumn 344, Issue 5, 2009, Pages 592-598

  Ochiai, Hirofumi ^a   Huang, Wei ^a   Wang, Lai Xi ^a  

^a UNIVERSITY OF MARYLAND SCHOOL OF MEDICINE   (United States)

Author keywords

Carbohydrate oxazoline derivative; Endoglycosidase; Enzymatic polymerization; Glycopeptides; Transglycosylation

Indexed keywords

ALTERNATIVE SYNTHESIS; ARTHROBACTER; CATALYTIC AMOUNTS; CATALYZED POLYMERIZATIONS; ENDOGLYCOSIDASE; ENZYMATIC POLYMERIZATION; ENZYMATIC REACTIONS; ENZYMATIC TRANSGLYCOSYLATION; GLUCOSE RESIDUES; GLYCOPEPTIDES; INTERMEDIATE PRODUCTS; N-ACETYL-GLUCOSAMINIDASE; REPEATING UNITS; TRANSGLYCOSYLATION;

BIOPOLYMERS; ENZYME ACTIVITY; GLUCOSE; MONOMERS; ORGANIC COMPOUNDS; PEPTIDES; POLYMERIZATION; POLYMERS; POLYSACCHARIDES; SYNTHESIS (CHEMICAL);

NITROGEN COMPOUNDS;

GLUCOSE; N ACETYL BETA GLUCOSAMINIDASE; OLIGOSACCHARIDE; OXAZOLINE DERIVATIVE;

ARTHROBACTER; ARTICLE; CATALYSIS; ENZYME ACTIVITY; ENZYME GLYCOSYLATION; POLYMERIZATION; PRIORITY JOURNAL; SYNTHESIS;

ARTHROBACTER; CARBOHYDRATE SEQUENCE; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DISACCHARIDES; GLYCOPEPTIDES; GLYCOSYLATION; MANNOSYL-GLYCOPROTEIN ENDO-BETA-N-ACETYLGLUCOSAMINIDASE; MODELS, MOLECULAR; MOLECULAR SEQUENCE DATA; SPECTROMETRY, MASS, MATRIX-ASSISTED LASER DESORPTION-IONIZATION;

ARTHROBACTER PROTOPHORMIAE;

EID: 62549118199     PISSN: 00086215     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carres.2009.01.016     Document Type: Article

References (36)

1. Faijes M., and Planas A. Carbohydr. Res. 342 (2007) 1581-1594
2. Kobayashi S., Uyama H., and Kimura S. Chem. Rev. 101 (2001) 3793-3818
3. Kobayashi S., Kiyosada T., and Shoda S. J. Am. Chem. Soc. 118 (1996) 13113-13114
4. Kobayashi S., Morii H., Itoh R., Kimura S., and Ohmae M. J. Am. Chem. Soc. 123 (2001) 11825-11826
5. Kobayashi S., Fujikawa S., and Ohmae M. J. Am. Chem. Soc. 125 (2003) 14357-14369
6. Ochiai H., Ohmae M., and Kobayashi S. Carbohydr. Res. 339 (2004) 2769-2788
7. Kobayashi S., Ohmae M., Ochiai H., and Fujikawa S. Chem. Eur. J. 12 (2006) 5962-5971
8. Ochiai H., Ohmae M., Mori T., and Kobayashi S. Biomacromolecules 8 (2007) 1327-1332
9. Kobayashi S., Makino A., Matsumoto H., Kunii S., Ohmae M., Kiyosada T., Makiguchi K., Matsumoto A., Horie M., and Shoda S. Biomacromolecules 7 (2006) 1644-1656
10. Takegawa K., Yamaguchi S., Kondo A., Iwamoto H., Nakoshi M., Kato I., and Iwahara S. Biochem. Int. 24 (1991) 849-855
11. Takegawa K., Yamaguchi S., Kondo A., Kato I., and Iwahara S. Biochem. Int. 25 (1991) 829-835
12. Yamamoto K., Kadowaki S., Watanabe J., and Kumagai H. Biochem. Biophys. Res. Commun. 203 (1994) 244-252
13. Yamamoto K. J. Biosci. Bioeng. 92 (2001) 493-501
14. Wang L.X. Carbohydr. Res. 343 (2008) 1509-1522
15. Fujita M., Shoda S., Haneda K., Inazu T., Takegawa K., and Yamamoto K. Biochim. Biophys. Acta 1528 (2001) 9-14
16. Li B., Zeng Y., Hauser S., Song H., and Wang L.X. J. Am. Chem. Soc. 127 (2005) 9692-9693
17. Li H., Li B., Song H., Breydo L., Baskakov I.V., and Wang L.X. J. Org. Chem. 70 (2005) 9990-9996
18. Zeng Y., Wang J., Li B., Hauser S., Li H., and Wang L.X. Chem. Eur. J. 12 (2006) 3355-3364
19. Rising T.W., Claridge T.D., Davies N., Gamblin D.P., Moir J.W., and Fairbanks A.J. Carbohydr. Res. 341 (2006) 1574-1596
20. Rising T.W., Claridge T.D., Moir J.W., and Fairbanks A.J. ChemBioChem 7 (2006) 1177-1180
21. Umekawa M., Huang W., Li B., Fujita K., Ashida H., Wang L.X., and Yamamoto K. J. Biol. Chem. 283 (2008) 4469-4479
22. Heidecke C.D., Ling Z., Bruce N.C., Moir J.W., Parsons T.B., and Fairbanks A.J. ChemBioChem 9 (2008) 2045-2051
23. Li B., Song H., Hauser S., and Wang L.X. Org. Lett. 8 (2006) 3081-3084
24. Ochiai H., Huang W., and Wang L.X. J. Am. Chem. Soc. 130 (2008) 13790-137803
25. Wei Y., Li C., Huang W., Li B., Strome S., and Wang L.X. Biochemistry 47 (2008) 10294-10304
26. Rising T.W., Heidecke C.D., Moir J.W., Ling Z., and Fairbanks A.J. Chem. Eur. J. 14 (2008) 6444-6464
27. Fan J.Q., Takegawa K., Iwahara S., Kondo A., Kato I., Abeygunawardana C., and Lee Y.C. J. Biol. Chem. 270 (1995) 17723-17729
28. Fujita K., Miyamura T., Sano M., Kato I., and Takegawa K. J. Biosci. Bioeng. 93 (2002) 614-617
29. Huang W., Ochiai H., Zhang X., and Wang L.X. Carbohydr. Res. 343 (2008) 2903-2913
30. Singh L., and Seifert J. Tetrahedron Lett. 42 (2001) 3133-3136
31. Crich D., and Dudkin V. J. Am. Chem. Soc. 123 (2001) 6819-6825
32. Lee Y.C. Anal. Biochem. 189 (1990) 151-162
33. Wang L.X., Ni J., Singh S., and Li H. Chem. Biol. 11 (2004) 127-134
34. Hancock S.M., Vaughan M.D., and Withers S.G. Curr. Opin. Chem. Biol. 10 (2006) 509-519
35. Li C., Huang W., and Wang L.X. Bioorg. Med. Chem. 16 (2008) 8366-8372
36. Fujita K., Tanaka N., Sano M., Kato I., Asada Y., and Takegawa K. Biochem. Biophys. Res. Commun. 267 (2000) 134-138