메뉴 건너뛰기




Volumn 17, Issue 4, 1999, Pages 305-317

Biotransformation of organic sulfides. Part 11. Preparation of functionalised phenyl propyl sulfoxides using helminthosporium species and mortierella isabellina

Author keywords

Acinetobacter calcoaceticus; Biocatalysis; Biotransformation; Helminthosporium; Mortierella isabellina; Sulfoxide

Indexed keywords

BACTERIA; BIOCONVERSION; CRYSTALLIZATION; OXIDATION; STEREOCHEMISTRY; SULFUR COMPOUNDS;

EID: 0032696378     PISSN: 10242422     EISSN: None     Source Type: Journal    
DOI: 10.3109/10242429909015233     Document Type: Article
Times cited : (16)

References (26)
  • 1
    • 1542473063 scopus 로고    scopus 로고
    • Remote asymmetric induction using chiral sulfoxides
    • Arai, Y. (1998). "Remote asymmetric induction using chiral sulfoxides". J. Synth. Org. Chem. Jpn., 56, 798-809.
    • (1998) J. Synth. Org. Chem. Jpn. , vol.56 , pp. 798-809
    • Arai, Y.1
  • 2
    • 37049083509 scopus 로고
    • Oxidation of methyl p-tolyl sulfide with baker's yeast: Preparation of a synthon of the mevinic acid-type hypocholestemic agents
    • Beecher, J., Brackenridge, I., Roberts, S.M., Tang, J. and Willetts, A.J. (1995). "Oxidation of methyl p-tolyl sulfide with baker's yeast: preparation of a synthon of the mevinic acid-type hypocholestemic agents". J. Chem. Soc. Perkin Trans. I, 1641-1643.
    • (1995) J. Chem. Soc. Perkin Trans. , vol.1 , pp. 1641-1643
    • Beecher, J.1    Brackenridge, I.2    Roberts, S.M.3    Tang, J.4    Willetts, A.J.5
  • 3
    • 84943506586 scopus 로고
    • Intramolecular reactions. VII. Cyclisation of aryl 3-chloropropyl sulfones
    • Bird, R. and Stirling, C.J.M. (1968). "Intramolecular reactions. VII. Cyclisation of aryl 3-chloropropyl sulfones". J. Chem. Soc. B, 111-114.
    • (1968) J. Chem. Soc. , vol.B , pp. 111-114
    • Bird, R.1    Stirling, C.J.M.2
  • 4
    • 0028896913 scopus 로고
    • (S)-α-Methoxyphenyl acetic acid: A new NMR chiral shift reagent for the stereochemical analysis of sulfoxides
    • Buist, P.H., Marecak, D., Holland, H.L. and Brown, F.M. (1995). "(S)-α-Methoxyphenyl acetic acid: a new NMR chiral shift reagent for the stereochemical analysis of sulfoxides". Tetrahedron: Asymmetry, 6, 7-10.
    • (1995) Tetrahedron: Asymmetry , vol.6 , pp. 7-10
    • Buist, P.H.1    Marecak, D.2    Holland, H.L.3    Brown, F.M.4
  • 6
    • 0006865326 scopus 로고
    • Kinetic implications of remote partcipation during photooxidation at sulfur
    • Clennan, E.L., Yang, K. and Chen, X. (1991). "Kinetic implications of remote partcipation during photooxidation at sulfur". J. Org. Chem., 56, 5251-5252.
    • (1991) J. Org. Chem. , vol.56 , pp. 5251-5252
    • Clennan, E.L.1    Yang, K.2    Chen, X.3
  • 7
    • 0000929588 scopus 로고
    • A convenient family of chiral shift reagents for measurement of enantiomeric excesses of sulfoxides
    • Deshmukh, M., Dunach, E., Juge, S. and Kagan, H.B. (1984). "A convenient family of chiral shift reagents for measurement of enantiomeric excesses of sulfoxides". Tetrahedron Lett., 25, 3467-3470.
    • (1984) Tetrahedron Lett. , vol.25 , pp. 3467-3470
    • Deshmukh, M.1    Dunach, E.2    Juge, S.3    Kagan, H.B.4
  • 8
    • 0001304650 scopus 로고
    • The chlorosulfonyl moiety as a leaving group: Hydride reduction of sulfonyl chlorides
    • Fong, H.O., Hardstaff, W.R., Kay, D.G., Langler, R.F., Morse, R.H. and Sandoval, D.N. (1979). "The chlorosulfonyl moiety as a leaving group: hydride reduction of sulfonyl chlorides". Can. J. Chem., 57, 1206-1213.
    • (1979) Can. J. Chem. , vol.57 , pp. 1206-1213
    • Fong, H.O.1    Hardstaff, W.R.2    Kay, D.G.3    Langler, R.F.4    Morse, R.H.5    Sandoval, D.N.6
  • 9
    • 0344177102 scopus 로고
    • Organic compounds and their pharmaceutical use
    • Goldsworthy, J., Marshall, W.S. and Verge, J.P. (1984). "Organic compounds and their pharmaceutical use". Brit. Pat 2128999; Chem. Abs. (1985) 102: 62-239.
    • (1984) Brit. Pat , pp. 2128999
    • Goldsworthy, J.1    Marshall, W.S.2    Verge, J.P.3
  • 10
    • 0344608786 scopus 로고
    • Goldsworthy, J., Marshall, W.S. and Verge, J.P. (1984). "Organic compounds and their pharmaceutical use". Brit. Pat 2128999; Chem. Abs. (1985) 102: 62-239.
    • (1985) Chem. Abs. , vol.102 , pp. 62-239
  • 11
    • 0000657398 scopus 로고
    • The oxidation of organic sulphides by mortierella isabellina. 2. Effects of substituents on the stereochemistry of sulphoxide formation
    • Holland, H.L., Popperl, H., Ninniss, R.W. and Chenehaiah, P.C. (1985). "The oxidation of organic sulphides by Mortierella isabellina. 2. Effects of substituents on the stereochemistry of sulphoxide formation". Can. J. Chem., 63, 1118-1120.
    • (1985) Can. J. Chem. , vol.63 , pp. 1118-1120
    • Holland, H.L.1    Popperl, H.2    Ninniss, R.W.3    Chenehaiah, P.C.4
  • 12
    • 0028475519 scopus 로고
    • Biotransformation of organic sulfides. IV. Formation of chiral benzyl alkyl and phenyl alkyl sulfoxides by Helminthosporium species NRRL 4671
    • Holland, H.L., Brown, F.M. and Larsen, B.G. (1994). "Biotransformation of organic sulfides. IV. Formation of chiral benzyl alkyl and phenyl alkyl sulfoxides by Helminthosporium species NRRL 4671". Bioorg. Med. Chem., 2, 647-652.
    • (1994) Bioorg. Med. Chem. , vol.2 , pp. 647-652
    • Holland, H.L.1    Brown, F.M.2    Larsen, B.G.3
  • 13
    • 0029130289 scopus 로고
    • Biotransformation of organic sulfides. Part 6. Formation of chiral para-substituted benzyl methyl sulfoxides by Helminthosporium species NRRL 4671
    • Holland, H.L., Brown, F.M. and Larsen, B.G. (1995). "Biotransformation of organic sulfides. Part 6. Formation of chiral para-substituted benzyl methyl sulfoxides by Helminthosporium species NRRL 4671". Tetrahedron: Asymmetry, 7, 1561-1567.
    • (1995) Tetrahedron: Asymmetry , vol.7 , pp. 1561-1567
    • Holland, H.L.1    Brown, F.M.2    Larsen, B.G.3
  • 14
    • 0030568598 scopus 로고    scopus 로고
    • Biotransformation of organic sulfides. Part 9. Formation of (S)-para-substituted phenyl methyl sulfoxides by biotransformation using Helminthosporium species NRRL 4671
    • Holland, H.L., Bornmann, M. and Lakshmaiah, G. (1996). "Biotransformation of organic sulfides. Part 9. Formation of (S)-para-substituted phenyl methyl sulfoxides by biotransformation using Helminthosporium species NRRL 4671". J. Mol. Catal. B: Enzymatic, 1, 97-102.
    • (1996) J. Mol. Catal. B: Enzymatic , vol.1 , pp. 97-102
    • Holland, H.L.1    Bornmann, M.2    Lakshmaiah, G.3
  • 15
    • 0031058146 scopus 로고    scopus 로고
    • Biotransformation of organic sulfides - VIII. A predictive model for sulfoxidation by Helminthosporium species NRRL 4671
    • Holland, H.L., Brown, F.M., Lakshmaiah, G., Larsen, B.G. and Patel, M. (1997a). "Biotransformation of organic sulfides - VIII. A predictive model for sulfoxidation by Helminthosporium species NRRL 4671". Tetrahedron: Asymmetry, 8, 683-697.
    • (1997) Tetrahedron: Asymmetry , vol.8 , pp. 683-697
    • Holland, H.L.1    Brown, F.M.2    Lakshmaiah, G.3    Larsen, B.G.4    Patel, M.5
  • 16
    • 0031561448 scopus 로고    scopus 로고
    • Side chain oxidation of aromatic compounds by fungi. 7. A rationale for sulfoxidation, benzylic hydroxylation and olefin oxidation by mortierella isabellina
    • Holland, H.L., Allen, L.J., Chernishenko, M.J., Diez, M., Kohl, A., Ozog, J. and Gu, J.-X. (1997b). "Side chain oxidation of aromatic compounds by fungi. 7. A rationale for sulfoxidation, benzylic hydroxylation and olefin oxidation by Mortierella isabellina". J. Mol. Cat. B: Enzymatic; 3, 311-324.
    • (1997) J. Mol. Cat. B: Enzymatic , vol.3 , pp. 311-324
    • Holland, H.L.1    Allen, L.J.2    Chernishenko, M.J.3    Diez, M.4    Kohl, A.5    Ozog, J.6    Gu, J.-X.7
  • 17
    • 0032570485 scopus 로고    scopus 로고
    • Biocatalytic and chemical preparation of all four diastereomers of methionine sulfoxide
    • Holland, H.L. and Brown, F.M. (1998). "Biocatalytic and chemical preparation of all four diastereomers of methionine sulfoxide". Tetrahedron: Asymmetry, 9, 535-538.
    • (1998) Tetrahedron: Asymmetry , vol.9 , pp. 535-538
    • Holland, H.L.1    Brown, F.M.2
  • 18
    • 0033014601 scopus 로고    scopus 로고
    • Enantioselective synthesis and pharmacological evaluation of a new type of verapamil analog with hypotensive and calcium antagonist activities
    • Holland, H.L., Gu, J.-X., Orallo, F., Camiña, M., Fabeiro, P. and Willetts, A.J. (1999). "Enantioselective synthesis and pharmacological evaluation of a new type of verapamil analog with hypotensive and calcium antagonist activities". Pharm. Res., 16, 281-287.
    • (1999) Pharm. Res. , vol.16 , pp. 281-287
    • Holland, H.L.1    Gu, J.-X.2    Orallo, F.3    Camiña, M.4    Fabeiro, P.5    Willetts, A.J.6
  • 19
    • 0345470979 scopus 로고
    • Condensation of p-bromothiophenol with alpha,omega-dihalo-substituted hydrocarbons
    • Kuliev, A.M., Usubova, E.N., Sultanov, Y.M. and Kuliev, A.B. (1967). "Condensation of p-bromothiophenol with alpha,omega-dihalo-substituted hydrocarbons". Azerb. Khim. Zh., 10-12; Chem. Abs. (1967) 67: 11-6673.
    • (1967) Azerb. Khim. Zh. , pp. 10-12
    • Kuliev, A.M.1    Usubova, E.N.2    Sultanov, Y.M.3    Kuliev, A.B.4
  • 20
    • 0344608785 scopus 로고
    • Kuliev, A.M., Usubova, E.N., Sultanov, Y.M. and Kuliev, A.B. (1967). "Condensation of p-bromothiophenol with alpha,omega-dihalo-substituted hydrocarbons". Azerb. Khim. Zh., 10-12; Chem. Abs. (1967) 67: 11-6673.
    • (1967) Chem. Abs. , vol.67 , pp. 116673
  • 21
    • 0029075087 scopus 로고
    • A predictive active site model for the cyclohexanone monooxygenase catalyzed oxidation of sulfides to chiral sulfoxides
    • Ottolina, G., Pasta, P., Carrea, G., Colonna, S., Dallavalle, S. and Holland, H.L. (1995). "A predictive active site model for the cyclohexanone monooxygenase catalyzed oxidation of sulfides to chiral sulfoxides". Tetrahedron: Asymmetry, 6, 1375-1386.
    • (1995) Tetrahedron: Asymmetry , vol.6 , pp. 1375-1386
    • Ottolina, G.1    Pasta, P.2    Carrea, G.3    Colonna, S.4    Dallavalle, S.5    Holland, H.L.6
  • 22
    • 0030561346 scopus 로고    scopus 로고
    • Active site model of cyclohexanone monooxygenase. 3. The case of benzyl sulfides bearing polar groups
    • Ottolina, G., Pasta, P., Varley, D. and Holland, H.L. (1996). "Active site model of cyclohexanone monooxygenase. 3. The case of benzyl sulfides bearing polar groups". Tetrahedron:Asymmetry, 7, 3427-3430.
    • (1996) Tetrahedron:asymmetry , vol.7 , pp. 3427-3430
    • Ottolina, G.1    Pasta, P.2    Varley, D.3    Holland, H.L.4
  • 23
    • 85077702395 scopus 로고
    • Asymmetric synthesis using nucleophilic reagents containing a chiral sulfoxide group
    • Solladié, G. (1981). "Asymmetric synthesis using nucleophilic reagents containing a chiral sulfoxide group". Synthesis, 185-196.
    • (1981) Synthesis , pp. 185-196
    • Solladié, G.1
  • 24
    • 0004909757 scopus 로고
    • A new and convenient synthetic method for cyclopropyl phenyl sulfides
    • Tanaka, K., Uneme, H., Matsui, S. and Kaji, A. (1982). "A new and convenient synthetic method for cyclopropyl phenyl sulfides". Bull. Chem. Soc. Jpn., 55, 2965-2972.
    • (1982) Bull. Chem. Soc. Jpn. , vol.55 , pp. 2965-2972
    • Tanaka, K.1    Uneme, H.2    Matsui, S.3    Kaji, A.4
  • 25
    • 0028789260 scopus 로고
    • Baker's yeast oxidation of methyl para-tolylsulfide: Synthesis of a chiral intermediate in the preparation of the mevinic acid-type hypocholestemic agents
    • Tang, J., Brackenridge, I., Roberts, S.M., Beecher, J. and Willetts, A.J. (1995). "Baker's yeast oxidation of methyl para-tolylsulfide: synthesis of a chiral intermediate in the preparation of the mevinic acid-type hypocholestemic agents". Tetrahedron, 51, 13 217-13 238.
    • (1995) Tetrahedron , vol.51 , pp. 13217-13238
    • Tang, J.1    Brackenridge, I.2    Roberts, S.M.3    Beecher, J.4    Willetts, A.J.5
  • 26
    • 0001165985 scopus 로고
    • Convenient synthesis of phenyl sulfides by a borohydride exchange resin-phenyl disulfide system in methanol
    • Yoon, N.M., Choi, J. and Ahn, J.H. (1994). "Convenient synthesis of phenyl sulfides by a borohydride exchange resin-phenyl disulfide system in methanol". J. Org. Chem., 59, 3490-3493.
    • (1994) J. Org. Chem. , vol.59 , pp. 3490-3493
    • Yoon, N.M.1    Choi, J.2    Ahn, J.H.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.