Biotransformation of α-bromo and α,α′-dibromo alkanone to α-hydroxyketone and α-diketone by Spirulina platensis

Journal of Molecular Catalysis B: Enzymatic

Volumn 45, Issue 1-2, 2007, Pages 68-72

  Utsukihara, Takamitsu ^a   Okada, Shinnosuke ^a   Kato, Nakahide ^a   Horiuchi, C Akira ^a  

^a RIKKYO UNIVERSITY   (Japan)

Author keywords

Hydroxyketone; Biotransformation; Bromo cycloalkanone; Dibromo cycloalkanone; Spirulina platensis

Indexed keywords

BIOTRANSFORMATION; BROMO CYCLOALKANONE; DIBROMO CYCLOALKANONE; HYDROXYKETONE; SPIRULINA PLATENSIS;

BROMINE COMPOUNDS; CARBONYLATION; CATALYSIS; MOLECULAR STRUCTURE; PHENOLS;

KETONES;

1,2 DICARBONYL DERIVATIVE; 2 BROMOCYCLOHEXANONE; 2 HYDROXYCYCLOHEXANONE; ALKANONE; ALKYL GROUP; BROMINE DERIVATIVE; CARBONYL DERIVATIVE; CYCLOHEXANONE DERIVATIVE; KETONE DERIVATIVE; PHENOL DERIVATIVE; UNCLASSIFIED DRUG;

ALGA; ARTICLE; BIOTRANSFORMATION; CONTROLLED STUDY; CYANIDIOSCHYZON MEROLAE; CYANIDIUM CALDARIUM; NONHUMAN; REACTION TIME; SPIRULINA PLATENSIS; SYNECHOCCUS ELONGATUS; SYNECHOSYSTIS;

ALGAE; CYANIDIOSCHYZON MEROLAE; CYANIDIUM CALDARIUM; SPIRULINA PLATENSIS;

EID: 33847319362     PISSN: 13811177     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.molcatb.2006.12.001     Document Type: Article

References (46)

1. Corey E.J., and Link J.O. Tetrahedron Lett. 31 (1990) 601
2. Corey E.J., and Link J.O. J. Org. Chem. 56 (1991) 442
3. Ramachandran P.V., Gong B., and Brown H.C. Chilrality 7 (1995) 103
4. Elks J., and Ganelli C.R. Dictionary of Drugs (1990), Chapman and Hall p. 1160
5. Taggart P., Sutton P., and Donaldson R. Clin. Sci. 69 (1985) 631
6. Wei Z.-L., Li Z.-Y., and Lin G.-Q. Tetrahedron 54 (1998) 13059
7. Vedejs E. J. Am. Chem. Soc. 96 (1974) 5944
8. Vedejs E., and Telschow J.E. J. Org. Chem. 41 (1976) 740
9. Vedejs E., and Larsen S. Org. Synth. Collect. VII (1990) 277
10. Gamboni R., and Tamm C. Tetrahedron Lett. 27 (1986) 3999
11. Cuvigny T., Valette G., Larcheveque M., and Normant H. J. Organomet. Chem. 155 (1978) 147
12. Rubottom G.M., Vazquez M.A., and Pelegrina D.R. Tetrahedron Lett. (1974) 4319
13. Horiguchi Y., Nakamura E., and Kuwajima I. Tetrahedron Lett. 30 (1989) 3323
14. Takai T., Yamada T., Rhode O., and Mukaiyama T. Chem. Lett. (1991) 281
15. Davis F.A., and Sheppard A.C. J. Org. Chem. 52 (1987) 954
16. Moriarty R.M., Hu H., and Gupta S.C. Tetrahedron Lett. 22 (1981) 1283
17. Moriaty R.M., Duncan M.P., and Prakash O. J. Chem. Soc. Perkin Trans. 1 (1987) 1781
18. Moriarty R.M., Berglund B.A., and Penmasta R. Tetrahedron Lett. 33 (1992) 6065
19. Utsukihara T., Nakamura H., Watanabe M., and Horiuchi C.A. Tetrahedron Lett. 47 (2006) 9359
20. Matsuura Y., Chai W., Endoh E., Suhara J., Hamada H., and Horiuchi C.A. Phytochemistry 61 (2002) 669
21. Sakamaki H., Kitanaka S., Chai W., Hayashida Y., Takagi Y., and Horiuchi C.A. J. Nat. Prod. 64 (2001) 630
22. Chai W., Sakamaki H., Kitanaka S., and Horiuchi C.A. Bull. Chem. Soc. Jpn. 76 (2003) 177
23. Chai W., Hamada H., Suhara J., and Horiuchi C.A. Phytochemistry 57 (2001) 669
24. Ishihara K., Hamada H., Hirata T., and Nakajima N. J. Mol. Catal. B: Enzym. 23 (2003) 145
25. Nakamura K., Kondo S., Kawai Y., Hida K., Kitano K., and Ohno A. Tetrahedron: Asymmetry 7 (1996) 409
26. Cui J., Ema T., Sakai T., and Utaka M. Tetrahedron: Asymmetry 9 (1998) 2692
27. Kawai Y., Hida K., Tsujimoto M., Kondo S., Kitano K., Nakamura K., and Ohno A. Bull. Chem. Soc. Jpn. 72 (1999) 99
28. Demir A.S., Hamamci H., Ayhan P., Duygu A.N., İgdir A.C., and Capanoglu D. Tetrahedron: Asymmetry 15 (2004) 2579
29. Carballeira J.D., Àlvarez E., Campillo M., Pardo L., and Sinisterra J.V. Tetrahedron: Asymmetry 15 (2004) 951
30. Utsukihara T., Misumi O., Kato N., Kuroiwa T., and Horiuchi C.A. Tetrahedron: Asymmetry 17 (2006) 1179
31. Utsukihara T., Chai W., Kato N., Nakamura K., and Horiuchi C.A. J. Mol. Catal. B: Enzym. 31 (2004) 19
32. Paul S., Gupta V., Gupta R., and Loupy A. Tetrahedron Lett. 44 (2003) 439
33. Dioxane-dibromide was prepared by adding drop wise bromine (8 ml) to dioxane (5 ml), until a yellow solid product was obtained. It was filtered dried in vacuum and stored in refrigerator (yield 10 g)
34. Utaka M., Matsushita S., and Takeda A. Chem. Lett. (1980) 779
35. El-Qisairi A.K., and Qaseer H.A. J. Organomet. Chem. 659 (2002) 50
36. Matsubara S., Takai K., and Nozaki H. Bull. Chem. Soc. Jpn. 56 (1983) 2029
37. Yadav J.S., Reddy B.V.S., Basak A.K., and Narsaiah A.V. Tetrahedron 60 (2004) 2131
38. Xuan Y.-Y., and Chen Z.-C. Synth. Commun. 32 (2002) 1875
39. Elipe M.V.S., Huskey S.W., and Zhu B. J. Pharm. Biomed. Anal. 30 (2003) 1431
40. Henrikson R. Earth Food Spirulina (1989), Ronore Enterprises Inc., California p. 180
41. Dillon J.C., Phuc A.P., and Dubacq J.P. World Rev. Nutr. Diet. 77 (1995) 32
42. Ciferri O., and Tiboni O. Annu. Rev. Microbiol. 39 (1985) 503
43. Aaronson S., Berner T., and Dubinsky Z. Microalgae as a Source of the Chemicals and Natural Products. In: Algae Biomass (1980), Biochemical Press, Elsevier p. 575
44. Richmond A. In: Borowitzka M.A., and Borowitzka L.J. (Eds). Microalgal Biotechnology (1988), Cambridge University Press, Cambridge 85
45. Henry B.S. In: Hendry G.A.F., and Houghton J.D. (Eds). Natural Food Colorants (1996), Blackil Academic Professional, London 40
46. Nakamura K., Yamanaka R., Tohi K., and Hamada H. Tetrahedron Lett. 41 (2000) 6799