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Volumn 23, Issue 8, 1999, Pages 827-832

Asymmetric oxidations at sulfur catalyzed by engineered strains that overexpress cyclohexanone monooxygenase

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOHEXANONE DERIVATIVE; SULFIDE; SULFOXIDE; SULFUR; UNSPECIFIC MONOOXYGENASE;

EID: 0032770016     PISSN: 11440546     EISSN: None     Source Type: Journal    
DOI: 10.1039/a902283j     Document Type: Article
Times cited : (106)

References (47)
  • 3
    • 0000101704 scopus 로고
    • ed. J.D. Morrison and J.W. Scott, Academic Press, New York
    • M. R. Barbachyn and C. R. Johnson, in Asymmetric Synthesis, ed. J. D. Morrison and J. W. Scott, Academic Press, New York, 1984. pp. 227-261.
    • (1984) Asymmetric Synthesis , pp. 227-261
    • Barbachyn, M.R.1    Johnson, C.R.2
  • 32
    • 0027291303 scopus 로고
    • For recent advances in NADPH regeneration technology applied to cyclohexanone monooxygenase, see F. Secundo, G. Carrea, S. Riva, E. Battistel and D. Bianchi, Biotechnol. Lett., 1993, 15, 865 and S. Rissom, U. Schwarlinek, M. Vogel, V. I. Tishkov and U. Kragl, Tetrahedron: Asymmetry, 1997, 8, 2523.
    • (1993) Biotechnol. Lett. , vol.15 , pp. 865
    • Secundo, F.1    Carrea, G.2    Riva, S.3    Battistel, E.4    Bianchi, D.5
  • 33
    • 0030738089 scopus 로고    scopus 로고
    • For recent advances in NADPH regeneration technology applied to cyclohexanone monooxygenase, see F. Secundo, G. Carrea, S. Riva, E. Battistel and D. Bianchi, Biotechnol. Lett., 1993, 15, 865 and S. Rissom, U. Schwarlinek, M. Vogel, V. I. Tishkov and U. Kragl, Tetrahedron: Asymmetry, 1997, 8, 2523.
    • (1997) Tetrahedron: Asymmetry , vol.8 , pp. 2523
    • Rissom, S.1    Schwarlinek, U.2    Vogel, M.3    Tishkov, V.I.4    Kragl, U.5
  • 40
    • 0009562389 scopus 로고    scopus 로고
    • note
    • In the case of phenyl n-propyl sulfide, extended reactions in the presence of the engineered yeast strain gave only a low yield of the corresponding (R)-sulfoxide in 25% ee. Neither ethyl thiophenylacetate nor methyl β-(thiophenyl)ethyl ether afforded any sulfoxide products, even after extended reaction times. Moreover, when the racemic sulfoxides derived from these thioethers were incubated with the yeast strain, all traces of the sulfoxides disappeared within 78 h. We did not investigate the fates of these materials further.
  • 43
    • 0009610623 scopus 로고    scopus 로고
    • Details of this construction are provided as Supplementary Material
    • Details of this construction are provided as Supplementary Material.
  • 46
    • 0009629355 scopus 로고    scopus 로고
    • note
    • Using racemic sulfoxide 5a and purified cyclohexanone monooxygenase, Colonna and co-workers estimated an enantioselectivity value of 12 for the oxidation of 5a to 7a.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.