메뉴 건너뛰기




Volumn 1811, Issue 12, 2011, Pages 1054-1061

Transformation of structurally diverse steroidal analogues by the fungus Corynespora cassiicola CBS 161.60 results in generation of 8β- monohydroxylated metabolites with evidence in favour of 8β-hydroxylation through inverted binding in the 9α-hydroxylase

Author keywords

8 Hydroxylation; Androgen; Biocatalyst; Corynespora cassiicola; Dual binding region; Progestogen

Indexed keywords

16ALPHA 17ALPHA EPOXY PREGN 4 ENE 3,20 DIONE; 8BETA 17ALPHA DIHYDROXY PREGN 4 EN 3,20 DIONE; 8BETA MONOHYDROXYLATED METABOLITE; 9ALPHA 15BETA DIHYDROXY PREGN 4 EN 3,20 DIONE; 9ALPHA HYDROXYLASE; ANDROSTENEDIONE; CORTICOSTEROID DERIVATIVE; CORTODOXONE; DRUG METABOLITE; FUNGAL ENZYME; GESTONORONE; HYDROXYPROGESTERONE ACETATE; OXYGENASE; PROGESTERONE; TESTOSTERONE; UNCLASSIFIED DRUG;

EID: 80155182004     PISSN: 13881981     EISSN: 18792618     Source Type: Journal    
DOI: 10.1016/j.bbalip.2011.09.016     Document Type: Article
Times cited : (13)

References (28)
  • 1
    • 0030896478 scopus 로고    scopus 로고
    • Advances in microbial steroid biotransformations
    • S.B. Mahato, and S. Garai Advances in microbial steroid biotransformations Steroids 62 1997 332 345
    • (1997) Steroids , vol.62 , pp. 332-345
    • Mahato, S.B.1    Garai, S.2
  • 2
    • 0035649181 scopus 로고    scopus 로고
    • Chemical and biochemical hydroxylations of steroids. A review
    • H. Pellissier, and M. Santelli Chemical and biochemical hydroxylations of steroids. A review Org. Prep. Proc. Int. 33 2001 1 58
    • (2001) Org. Prep. Proc. Int. , vol.33 , pp. 1-58
    • Pellissier, H.1    Santelli, M.2
  • 4
    • 79751536544 scopus 로고    scopus 로고
    • Microbial Baeyer-Villiger oxidation of steroidal ketones using Beauveria bassiana: Presence of an 11α-hydroxyl group essential to generation of d-homo lactones
    • A. Świzdor, T. Kołek, A. Panek, and A. Białoń ska Microbial Baeyer-Villiger oxidation of steroidal ketones using Beauveria bassiana: presence of an 11α-hydroxyl group essential to generation of d-homo lactones Biochim. Biophys. Acta Mol. Cell Biol. Lipid 1811 2011 253 262
    • (2011) Biochim. Biophys. Acta Mol. Cell Biol. Lipid , vol.1811 , pp. 253-262
    • Świzdor, A.1    Kołek, T.2    Panek, A.3    Białońska, A.4
  • 5
    • 74449086578 scopus 로고    scopus 로고
    • Transformation of some 3α-substituted steroids by Aspergillus tamarii KITA reveals stereochemical restriction of steroid binding orientation in the minor hydroxylation pathway
    • A.C. Hunter, H. Khuenl-Brady, P. Barrett, H.T. Dodd, and C. Dedi Transformation of some 3α-substituted steroids by Aspergillus tamarii KITA reveals stereochemical restriction of steroid binding orientation in the minor hydroxylation pathway J. Steroid Biochem. Mol. Biol. 118 2010 171 176
    • (2010) J. Steroid Biochem. Mol. Biol. , vol.118 , pp. 171-176
    • Hunter, A.C.1    Khuenl-Brady, H.2    Barrett, P.3    Dodd, H.T.4    Dedi, C.5
  • 6
    • 77958474237 scopus 로고    scopus 로고
    • Transformation of a series of saturated isomeric steroidal diols by Aspergillus tamarii KITA reveals a precise stereochemical requirement for entrance into the lactonization pathway
    • A.C. Hunter, C. Collins, H.T. Dodd, C. Dedi, and S.-J. Koussoroplis Transformation of a series of saturated isomeric steroidal diols by Aspergillus tamarii KITA reveals a precise stereochemical requirement for entrance into the lactonization pathway J. Steroid Biochem. Mol. Biol. 122 2010 352 358
    • (2010) J. Steroid Biochem. Mol. Biol. , vol.122 , pp. 352-358
    • Hunter, A.C.1    Collins, C.2    Dodd, H.T.3    Dedi, C.4    Koussoroplis, S.-J.5
  • 8
    • 50549201006 scopus 로고
    • 8β-hydroxylation of Reichstein's substances by microorganism
    • K. Tori, and E. Kondo 8β-hydroxylation of Reichstein's substances by microorganism Tetrahedron Lett. 10 1963 645 650
    • (1963) Tetrahedron Lett. , vol.10 , pp. 645-650
    • Tori, K.1    Kondo, E.2
  • 9
    • 0027286004 scopus 로고
    • Two novel microbial conversion products of progesterone derivatives
    • D. Krischenowski, and K. Kieslich Two novel microbial conversion products of progesterone derivatives Steroids 58 1993 278 281
    • (1993) Steroids , vol.58 , pp. 278-281
    • Krischenowski, D.1    Kieslich, K.2
  • 13
    • 36849091348 scopus 로고    scopus 로고
    • Metabolism of androst-4-en-3,17-dione by the filamentous fungus Neurospora crassa
    • DOI 10.1016/j.steroids.2007.06.008, PII S0039128X07001122
    • M.A. Faramarzi, M. Aghelnejad, M.T. Yazdi, M. Amini, and N. Hajarolasvadi Metabolism of androst-4-en-3,17-dione by the filamentous fungus Neurospora crassa Steroids 73 2008 13 18 (Pubitemid 350236288)
    • (2008) Steroids , vol.73 , Issue.1 , pp. 13-18
    • Faramarzi, M.A.1    Aghelnejad, M.2    Tabatabaei Yazdi, M.3    Amini, M.4    Hajarolasvadi, N.5
  • 14
    • 67650693707 scopus 로고    scopus 로고
    • An unusual ring-A opening and other reactions in steroid transformation by the thermophilic fungus Myceliophthora thermophila
    • A.C. Hunter, K.R. Watts, C. Dedi, and H.T. Dodd An unusual ring-A opening and other reactions in steroid transformation by the thermophilic fungus Myceliophthora thermophila J. Steroid Biochem. Mol. Biol. 116 2009 171 177
    • (2009) J. Steroid Biochem. Mol. Biol. , vol.116 , pp. 171-177
    • Hunter, A.C.1    Watts, K.R.2    Dedi, C.3    Dodd, H.T.4
  • 15
    • 0019810053 scopus 로고
    • Confirmation of progesterone side chain: Conflict between X-ray data and force-field calculations
    • W.L. Duax, J.F. Griffin, and D.C. Rohrer Conformation of progesterone side chain: conflict between X-ray data and force field calculations J. Am. Chem. Soc. 103 1981 6705 6712 (Pubitemid 12194504)
    • (1981) Journal of the American Chemical Society , vol.103 , Issue.22 , pp. 6705-6712
    • Duax, W.L.1    Griffin, J.F.2    Rohrer, D.C.3
  • 16
    • 0017606284 scopus 로고
    • Steroid structure and function I. Conformational transmission in 17α acetoxy progesterone
    • W.L. Duax, V. Cody, and J. Hazel Steroid structure and function 1. Conformational transmission in 17α-acetoxy progesterone Steroids 30 1977 471 480 (Pubitemid 8284176)
    • (1977) Steroids , vol.30 , Issue.4 , pp. 471-480
    • Duax, W.L.1    Cody, V.2    Hazel, J.3
  • 17
    • 0015912235 scopus 로고
    • A comparison of the molecular structures of six corticosteroids
    • C.M. Weeks, W.L. Duax, and M.E. Wolff A comparison of the molecular structures of six corticosteroids J. Am. Chem. Soc. 95 1973 2865 2868
    • (1973) J. Am. Chem. Soc. , vol.95 , pp. 2865-2868
    • Weeks, C.M.1    Duax, W.L.2    Wolff, M.E.3
  • 20
    • 0015536381 scopus 로고
    • The microbiological hydroxylation of steroids and related compounds
    • E.R.H. Jones The microbiological hydroxylation of steroids and related compounds Pure Appl. Chem. 33 1973 39 52
    • (1973) Pure Appl. Chem. , vol.33 , pp. 39-52
    • Jones, E.R.H.1
  • 21
    • 37049138213 scopus 로고
    • Microbiological hydroxylation of 17-norkauran-16-one and ent-17-norkauran-16-one with the fungus Rhizopus nigricans
    • R. McCrindle, J.K. Turnbull, and A.B. Anderson Microbiological hydroxylation of 17-norkauran-16-one and ent-17-norkauran-16-one with the fungus Rhizopus nigricans J. Chem. Soc. Perkin Trans. 1 13 1975 1202 1208
    • (1975) J. Chem. Soc. Perkin Trans. , vol.1 , Issue.13 , pp. 1202-1208
    • McCrindle, R.1    Turnbull, J.K.2    Anderson, A.B.3
  • 22
    • 34548647595 scopus 로고    scopus 로고
    • Distinct metabolic handling of 3β-hydroxy-17a-oxa-D-homo-5α- androstan-17-one by the filamentous fungus Aspergillus tamarii KITA: Evidence in support of steroid/hydroxylase binding hypothesis
    • DOI 10.1016/j.bbalip.2007.07.001, PII S1388198107001503
    • A.C. Hunter, and H. Bergin-Simpson Distinct metabolic handling of 3β-hydroxy-17a-oxa-d-homo-5α-androstan-17-one by the filamentous fungus Aspergillus tamarii KITA: evidence in support of steroid/hydroxylase binding hypothesis Biochim. Biophys. Acta Mol. Cell Biol. Lipid 1771 2007 1254 1261 (Pubitemid 47404972)
    • (2007) Biochimica et Biophysica Acta - Molecular and Cell Biology of Lipids , vol.1771 , Issue.9 , pp. 1254-1261
    • Hunter, A.C.1    Bergin-Simpson, H.2
  • 23
    • 27544462342 scopus 로고    scopus 로고
    • Role of protein dynamics in reaction rate enhancement by enzymes
    • DOI 10.1021/ja055251s
    • P.K. Agarwal Role of protein dynamics in reaction rate enhancement by enzymes J. Am. Chem. Soc. 127 2005 15248 15256 (Pubitemid 41547393)
    • (2005) Journal of the American Chemical Society , vol.127 , Issue.43 , pp. 15248-15256
    • Agarwal, P.K.1
  • 26
    • 0037317465 scopus 로고    scopus 로고
    • Pseudo-symmetry of C19-steroids, alternative binding orientations and multispecificity in human estrogenic 17β-hydroxysteroid dehydrogenase
    • 10.1096/fj.02-0397fje
    • A. Gangloff, R. Shi, V. Nahoum, and S.-X. Lin Pseudo-symmetry of C19-steroids, alternative binding orientations and multispecificity in human estrogenic 17β-hydroxysteroid dehydrogenase FASEB J. 16 2002 10.1096/fj.02-0397fje
    • (2002) FASEB J. , vol.16
    • Gangloff, A.1    Shi, R.2    Nahoum, V.3    Lin, S.-X.4
  • 27
    • 19444382188 scopus 로고    scopus 로고
    • Fate of novel Quasi reverse steroidal substrates by Aspergillus tamarii KITA: Bypass of lactonisation and an exclusive role for the minor hydroxylation pathway
    • DOI 10.1016/j.bbalip.2005.02.009, PII S1388198105000417
    • A.C. Hunter, S. Kennedy, S.-J. Clabby, and J. Elsom Fate of novel Quasi reverse steroidal substrates by Aspergillus tamarii KITA: bypass of lactonization and an exclusive role for the minor hydroxylation pathway Biochim. Biophys. Acta Mol. Cell Biol. Lipid 1734 2005 190 197 (Pubitemid 40724785)
    • (2005) Biochimica et Biophysica Acta - Molecular and Cell Biology of Lipids , vol.1734 , Issue.2 , pp. 190-197
    • Hunter, A.C.1    Kennedy, S.2    Clabby, S.-J.3    Elsom, J.4
  • 28
    • 25144473534 scopus 로고    scopus 로고
    • Two states and two more in the mechanisms of hydroxylation and epoxidation by cytochrome P450
    • DOI 10.1021/ja053847+
    • H. Hirao, D. Kumar, W. Thiel, and S. Shaik Two states and two more in the mechanisms of hydroxylation and epoxidation by cytochrome P450 J. Am. Chem. Soc. 127 2005 13007 13018 (Pubitemid 41339186)
    • (2005) Journal of the American Chemical Society , vol.127 , Issue.37 , pp. 13007-13018
    • Hirao, H.1    Kumar, D.2    Thiel, W.3    Shaik, S.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.