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Volumn , Issue 2, 1997, Pages 156-158

Chemoenzymatic synthesis of (S)-(-)-frontalin using bacterial epoxide hydrolases

Author keywords

biocatalysis; epoxide hydrolase; Rhodococcus equi

Indexed keywords

FRONTALIN; PHEROMONE;

EID: 0031046832     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-1153     Document Type: Article
Times cited : (43)

References (27)
  • 1
    • 84977418857 scopus 로고
    • Vité, J. P.; Francke, W. Chem. Unserer Zeit 1985, 19, 11. Vité, J. P.; Billings, C. W.; Mori, K. Naturwissensch. 1985, 72, 99.
    • (1985) Chem. Unserer Zeit , vol.19 , pp. 11
    • Vité, J.P.1    Francke, W.2
  • 3
    • 8044228400 scopus 로고    scopus 로고
    • note
    • More precisely the absolute configuration is 1S,5R; for reasons of simplicity, only the configuration at C-1 is denoted in the chemical literature.
  • 6
    • 34548195065 scopus 로고
    • Mulzer, J.; Altenbach, H.-J.; Braun, M.; Krohn, K.; Reissig, H.-U. Eds.; Verlag Chemie: Weinheim
    • Braun, M. Frontalin, In: Organic Synthesis Highlights, Mulzer, J.; Altenbach, H.-J.; Braun, M.; Krohn, K.; Reissig, H.-U. Eds.; Verlag Chemie: Weinheim, 1991; pp 335-343.
    • (1991) Organic Synthesis Highlights , pp. 335-343
    • Frontalin, B.M.1
  • 10
    • 0000660907 scopus 로고    scopus 로고
    • For a review on microbial epoxide hydrolases, see: Faber, K.; Mischitz, M.; Kroutil, W. Acta Chem. Scand. 1996, 50, 249. For a recent application of fungal enzymes, see: Pedragosa-Moreau, P.; Archelas, A.; Furstoss, R. Tetrahedron 1996, 52, 4593.
    • (1996) Acta Chem. Scand. , vol.50 , pp. 249
    • Faber, K.1    Mischitz, M.2    Kroutil, W.3
  • 11
    • 0029881420 scopus 로고    scopus 로고
    • For a review on microbial epoxide hydrolases, see: Faber, K.; Mischitz, M.; Kroutil, W. Acta Chem. Scand. 1996, 50, 249. For a recent application of fungal enzymes, see: Pedragosa-Moreau, P.; Archelas, A.; Furstoss, R. Tetrahedron 1996, 52, 4593.
    • (1996) Tetrahedron , vol.52 , pp. 4593
    • Pedragosa-Moreau, P.1    Archelas, A.2    Furstoss, R.3
  • 13
    • 8044226021 scopus 로고    scopus 로고
    • For experimental details, see reference 8
    • For experimental details, see reference 8.
  • 15
    • 8044229418 scopus 로고    scopus 로고
    • The decomposition presumably took place via acetal cleavage and subsequent rearrangement of the oxo epoxide formed
    • The decomposition presumably took place via acetal cleavage and subsequent rearrangement of the oxo epoxide formed.
  • 22
    • 8044227214 scopus 로고    scopus 로고
    • For a general procedure, reference 8
    • For a general procedure, reference 8.
  • 25
    • 0001194360 scopus 로고
    • This is particularly important since enzymatic epoxide hydrolysis may proceed via retention or inversion of configuration, see: Pedragosa-Moreau, S.; Archelas, A.; Furstoss, R. J. Org. Chem. 1993, 58, 5533.
    • (1993) J. Org. Chem. , vol.58 , pp. 5533
    • Pedragosa-Moreau, S.1    Archelas, A.2    Furstoss, R.3
  • 26
    • 85085845101 scopus 로고    scopus 로고
    • note
    • 2O (0.03 2g/L).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.