A practical one-step synthesis of 1,2-oxazoline derivatives from unprotected sugars and its application to chemoenzymatic β-N- acetylglucosaminidation of disialo-oligosaccharide

Helvetica Chimica Acta

Volumn 95, Issue 10, 2012, Pages 1928-1936

  Noguchi, Masato ^a   Fujieda, Tsukasa ^a   Huang, Wei Chun ^a   Ishihara, Masaki ^a   Kobayashi, Atsushi ^a   Shoda, Shin Ichiro ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

N Acetylglucosaminidation; Oxazoles, 4,5 dihydro ; Transglycosylation, chemo enzymatic

Indexed keywords

2-OXAZOLINE; ANOMERICS; CONDENSING AGENTS; ENZYMATIC GLYCOSYLATION; GLYCOSYL DONORS; OH GROUP; ONE STEP SYNTHESIS; OXAZOLES; OXAZOLINES; PRACTICAL METHOD; PROTECTING GROUP; SYNTHETIC INTERMEDIATES; TRANSGLYCOSYLATION;

AMINO SUGARS; CHLORINE COMPOUNDS; GLYCOSYLATION; OLIGOSACCHARIDES;

NITROGEN COMPOUNDS;

1,2 OXAZOLINE DERIVATIVE; ACETYLGLUCOSAMINIDASE; AMINOGLYCOSIDE DERIVATIVE; DISIALO OLIGOSACCHARIDE; HYDROXIDE; IMIDAZOLE DERIVATIVE; OLIGOSACCHARIDE; OXAZOLE DERIVATIVE; OXAZOLINE DERIVATIVE; UNCLASSIFIED DRUG; WATER;

ARTICLE; CATALYSIS; CHEMICAL REACTION; ENZYME GLYCOSYLATION; PRIORITY JOURNAL; SYNTHESIS;

EID: 84867700072     PISSN: 0018019X     EISSN: 15222675     Source Type: Journal    
DOI: 10.1002/hlca.201200414     Document Type: Article

References (22)

1. C.-H. Wong, G. M. Whitesides, in 'Enzymes in Synthetic Organic Chemistry', Pergamon, 1994.
2. K. G. I. Nilsson, 'Synthesis with Glycosidases', in 'Modern Methods in Carbohydrate Synthesis', Eds. S. H. Khan, R. A. O'Neill, Harwood Academic Publishers, 1996, pp. 518-547.
3. D. J. Vocadlo, S. G. Withers, 'Gycosidase-Catalysed Oligosaccharide Synthesis', in 'Carbohydrates in Chemistry and Biology', Eds. B. Ernst, G. W. Hart, P. Sina¿, Wiley-VCH, Weinheim, 2000, Vol. 2, pp. 723-844.
4. S. Shoda, 'Enzymatic Glycosylation', in 'Glycoscience', Eds. B. O. Fraser-Reid, K. Tatsuta, J. Thiem, Springer-Verlag, Berlin, Heidelberg, New York, 2001, Vol. II, pp. 1465-1496.
5. P. Bojarová-Fialová, V. Kaen, in 'Comprehensive Glycoscience', Ed. J. P. Kamerling, 2007, Elsevier Oxford, 2007, Vol. 1, pp. 453-487.
6. J. Thimm, J. Thiem, in 'Glycoscience', Eds. B. O. Fraser-Reid, K. Tatsuta, J. Thiem, Springer-Verlag, Berlin, Heidelberg, New York, 2008, Vol. II, pp. 1387-1409.
7. S. Kobayashi, T. Kiyosada, S. Shoda, J. Am. Chem. Soc. 1996, 118, 13113.
8. S. Kobayashi, H. Morii, R. Itoh, S. Kimura, M. Ohmae, J. Am. Chem. Soc. 2001, 123, 11825.
9. S. Shoda, M. Fujita, C. Lohavisavapanichi, Y. Misawa, K. Ushizaki, Y. Tawata, M. Kuriyama, M. Kohri, H. Kuwata, T. Watanabe, Helv. Chim. Acta 2002, 85, 3919.
10. S. Kobayashi, S. Fujikawa, M. Ohmae, J. Am. Chem. Soc. 2003, 125, 14357.
11. S. Shoda, M. Kohri, A. Kobayashi, 'Glycosidase-catalyzed synthesis of oligosaccharides through intermediate analogue substrates', in 'Biocatalysis: Chemistry and Biology', Ed. A. Tricone, Research Signpost, Kerala, 2005, pp. 83-98.
12. S. Kobayashi, M. Ohmae, H. Ochiai, S. Fujikawa, Chem.-Eur. J. 2006, 12, 5962.
13. M. Kohri, A. Kobayashi, M. Noguchi, S. Kawaida, T. Watanabe, S. Shoda, Holzforschung 2006, 60, 485.
14. S. Nakabayashi, C. D. Warren, R. W. Jeanloz, Carbohydr. Res. 1986, 150, c7.
15. M. Colon, M. M. Staveski, J. T. Davis, Tetrahedron Lett. 1991, 32, 4447.
16. S. Shoda, R. Izumi, M. Suenaga, K. Saito, M. Fujita, Chem. Lett. 2002, 31, 150.
17. M. Noguchi, T. Tanaka, H. Gyakushi, A. Kobayashi, S. Shoda, J. Org. Chem. 2009, 74, 2210.
18. M. Umekawa, T. Higashiyama, Y. Koga, T. Tanaka, M. Noguchi, A. Kobayashi, S. Shoda, W. Huang, L.-X. Wang, H. Ashida, K. Yamamoto, Biochim. Biophys. Acta-Gen. Subj. 2010, 1800, 1203.
19. N. Yoshida, T. Tanaka, M. Noguchi, A. Kobayashi, K. Ishikura, T. Ikenuma, H. Seno, T. Watanabe, M. Kohri, S. Shoda, Chem. Lett. 2012, 41, 689.
20. A. Toulmin, J. M. Wood, P. W. Kenny, J. Med. Chem. 2008, 51, 3720.
21. Z. Yang, J. Wang, L. Li, C. Ye, H. Liu, J. Heterocycl. Chem. 2009, 46, 788.
22. G. Vernin, H. Domlog, C. Siv, J. Metzger, A. K. El-Shafei, J. Heterocycl. Chem. 1981, 18, 85.