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Journal of Molecular Catalysis B: Enzymatic

Volumn 67, Issue 3-4, 2010, Pages 172-178

Biooxidation of methyl group: Part 2. Evidences for the involvement of cytochromes P450 in microbial multistep oxidation of terfenadine

(3) El Ouarradi, Amane a Lombard, Murielle a Buisson, Didier a

a UNIVERSITÉ PARIS DESCARTES (France)

Author keywords

Aldehyde; Biotransformation; Hydroxylation; Labeling study; P450 inhibitors; Streptomyces platensis

Indexed keywords

ACTIVE METABOLITES; BIO-OXIDATION; BIOTRANSFORMATION; CULTURE MEDIUM; CYTOCHROMES P450; FEXOFENADINE; FLUCONAZOLE; METHYL GROUP; MICROBIAL OXIDATION; MULTISTEP OXIDATION; OXIDATION ACTIVITIES; OXIDATION REACTIONS; P450 INHIBITORS; PLATENSIS; STREPTOMYCES PLATENSIS; TERFENADINE; WHOLE CELL;

ALDEHYDES; ARGON; BIOCONVERSION; CARBOXYLIC ACIDS; CELL CULTURE; FUNCTIONAL GROUPS; HYDROXYLATION;

OXIDATION;

ALCOHOL; ALDEHYDE; ARGON; CATALASE; CLOTRIMAZOLE; CYTOCHROME P450; CYTOCHROME P450 INHIBITOR; FEXOFENADINE; FLUCONAZOLE; OXIDOREDUCTASE; TERFENADINE;

ACTINOBACTERIA; ARTICLE; ATMOSPHERE; BIOTRANSFORMATION; CATALYSIS; CONTROLLED STUDY; CULTURE MEDIUM; DRUG HYDROXYLATION; DRUG OXIDATION; DRUG TRANSFORMATION; ENZYME ACTIVITY; HYDROXYLATION; METABOLITE; MICROBIAL METABOLISM; NONHUMAN; SOYBEAN; STREPTOMYCES; STREPTOMYCES PLATENSIS; WHOLE CELL;

GLYCINE MAX; STREPTOMYCES PLATENSIS;

EID: 78049274082 PISSN: 13811177 EISSN: None Source Type: Journal
DOI: 10.1016/j.molcatb.2010.07.017 Document Type: Article

Times cited : (3)

References (56)

1
- 4544283832
- B. Buhler, and A. Schmid J. Biotechnol. 113 2004 183 210
- (2004) J. Biotechnol. , vol.113 , pp. 183-210
- Buhler, B.¹ Schmid, A.²

2
- 0036900263
- A.J.J. Straathof, S. Panke, and A. Schmid Curr. Opin. Biotechnol. 13 2002 548
- (2002) Curr. Opin. Biotechnol. , vol.13 , pp. 548
- Straathof, A.J.J.¹ Panke, S.² Schmid, A.³

3
- 27844462042
- A.S. Bommarus, and K.M. Polizzi Chem. Eng. Sci. 61 2006 1004 1016
- (2006) Chem. Eng. Sci. , vol.61 , pp. 1004-1016
- Bommarus, A.S.¹ Polizzi, K.M.²

4
- 0031952975
- A. Markham, and A. Wagstaff Drugs 55 1998 269 274
- (1998) Drugs , vol.55 , pp. 269-274
- Markham, A.¹ Wagstaff, A.²

5
- 0034028814
- K. Simpson, and B. Jarvis Drugs 59 2000 301 321
- (2000) Drugs , vol.59 , pp. 301-321
- Simpson, K.¹ Jarvis, B.²

6
- 78049271584
- US Patent 5,990,127, Hoechst Marion Roussel, Deutchland
- J. Meiwes, M. Worm, US Patent 5,990,127, Hoechst Marion Roussel, Deutchland (1999).
- (1999)
- Meiwes, J.¹ Worm, M.²

7
- 78049311519
- WO Patent 47693, Hoechst Marion Roussel, Puteaux, Fr
- R. Azerad, J. Biton, I. Lacroix, WO Patent 47693, Hoechst Marion Roussel, Puteaux, Fr (1999).
- (1999)
- Azerad, R.¹ Biton, J.² Lacroix, I.³

8
- 55549113984
- A. El Ouarradi, I. Salar-Arnaud, and D. Buisson Tetrahedron 64 2008 11738 11744
- (2008) Tetrahedron , vol.64 , pp. 11738-11744
- El Ouarradi, A.¹ Salar-Arnaud, I.² Buisson, D.³

9
- 5344251671
- C. Mazier, M. Jaouen, M.-A. Sari, and D. Buisson Bioorg. Med. Chem. Lett. 14 2004 5423 5426
- (2004) Bioorg. Med. Chem. Lett. , vol.14 , pp. 5423-5426
- Mazier, C.¹ Jaouen, M.² Sari, M.-A.³ Buisson, D.⁴

10
- 0036138482
- S.G. Burton, D.A. Cowan, and J.M. Woodley Nat. Biotechnol. 20 2002 37 45
- (2002) Nat. Biotechnol. , vol.20 , pp. 37-45
- Burton, S.G.¹ Cowan, D.A.² Woodley, J.M.³

11
- 1942439106
- W. Kroutil, H. Mang, K. Edegger, and K. Faber Adv. Synth. Catal. 346 2004 125 142
- (2004) Adv. Synth. Catal. , vol.346 , pp. 125-142
- Kroutil, W.¹ Mang, H.² Edegger, K.³ Faber, K.⁴

12
- 33745759460
- F. Molinari Curr. Org. Chem. 10 2006 1247 1263
- (2006) Curr. Org. Chem. , vol.10 , pp. 1247-1263
- Molinari, F.¹

13
- 0039812510
- M. Sono, M.P. Roach, E.D. Coulter, and J.H. Dawson Chem. Rev. 96 1996 2841 2887
- (1996) Chem. Rev. , vol.96 , pp. 2841-2887
- Sono, M.¹ Roach, M.P.² Coulter, E.D.³ Dawson, J.H.⁴

14
- 38349076961
- J. Hirano, K. Miyamoto, and H. Ohta Tetrahedron Lett. 49 2008 1217 1219
- (2008) Tetrahedron Lett. , vol.49 , pp. 1217-1219
- Hirano, J.¹ Miyamoto, K.² Ohta, H.³

15
- 33748240975
- a. Kiener Angew. Chem. Int. Ed. Eng. 31 1992 774 775
- (1992) Angew. Chem. Int. Ed. Eng. , vol.31 , pp. 774-775
- Kiener, A.¹

16
- 0242438894
- N.M. Shaw, K.T. Robins, and A. Kiener Adv. Synth. Catal. 345 2003 425 435
- (2003) Adv. Synth. Catal. , vol.345 , pp. 425-435
- Shaw, N.M.¹ Robins, K.T.² Kiener, A.³

17
- 0040784571
- B. Buhler, A. Schmid, B. Hauer, and B. Witholt J. Biol. Chem. 275 2000 10085 10092
- (2000) J. Biol. Chem. , vol.275 , pp. 10085-10092
- Buhler, B.¹ Schmid, A.² Hauer, B.³ Witholt, B.⁴

18
- 0036156621
- B. Buhler, B. Witholt, B. Hauer, and A. Schmid Appl. Environ. Microbiol. 68 2002 560 568
- (2002) Appl. Environ. Microbiol. , vol.68 , pp. 560-568
- Buhler, B.¹ Witholt, B.² Hauer, B.³ Schmid, A.⁴

19
- 0035859869
- K.J. French, M.D. Strickler, D.A. Rock, D.A. Rock, G.A. Bennett, J.L. Wahlstrom, B.M. Goldstein, and J.P. Jones Biochemistry 40 2001 9532 9538
- (2001) Biochemistry , vol.40 , pp. 9532-9538
- French, K.J.¹ Strickler, M.D.² Rock, D.A.³ Rock, D.A.⁴ Bennett, G.A.⁵ Wahlstrom, J.L.⁶ Goldstein, B.M.⁷ Jones, J.P.⁸

20
- 0142104398
- W.H. Eschenfeldt, Y.Y. Zhang, H. Samaha, L. Stols, L.D. Eirich, C.R. Wilson, and M.I. Donnelly Appl. Environ. Microbiol. 69 2003 5992 5999
- (2003) Appl. Environ. Microbiol. , vol.69 , pp. 5992-5999
- Eschenfeldt, W.H.¹ Zhang, Y.Y.² Samaha, H.³ Stols, L.⁴ Eirich, L.D.⁵ Wilson, C.R.⁶ Donnelly, M.I.⁷

21
- 4143052728
- L.D. Eirich, D.L. Craft, L. Steinberg, A. Asif, W.H. Eschenfeldt, L. Stols, M.I. Donnelly, and C.R. Wilson Appl. Environ. Microbiol. 70 2004 4872 4879
- (2004) Appl. Environ. Microbiol. , vol.70 , pp. 4872-4879
- Eirich, L.D.¹ Craft, D.L.² Steinberg, L.³ Asif, A.⁴ Eschenfeldt, W.H.⁵ Stols, L.⁶ Donnelly, M.I.⁷ Wilson, C.R.⁸

22
- 33646589619
- H. Uchida, Y. Okamura, H. Yamanaka, T. Fukuda, S. Haneda, K. Aisaka, and Y. Fujii World J. Microbiol. Biotechnol. 22 2006 469 474
- (2006) World J. Microbiol. Biotechnol. , vol.22 , pp. 469-474
- Uchida, H.¹ Okamura, Y.² Yamanaka, H.³ Fukuda, T.⁴ Haneda, S.⁵ Aisaka, K.⁶ Fujii, Y.⁷

23
- 42549128183
- Y. Maeda, A. Yagyu, A. Sakurai, Y. Fujii, and H. Uchida World J. Microbiol. Biotechnol. 24 2008 797 804
- (2008) World J. Microbiol. Biotechnol. , vol.24 , pp. 797-804
- Maeda, Y.¹ Yagyu, A.² Sakurai, A.³ Fujii, Y.⁴ Uchida, H.⁵

24
- 33749051652
- M. Hofrichter, and R. Ullrich Appl. Microbiol. Biotechnol. 71 2006 276 288
- (2006) Appl. Microbiol. Biotechnol. , vol.71 , pp. 276-288
- Hofrichter, M.¹ Ullrich, R.²

25
- 0027331935
- H. Schwartz, R.E. Licht, and H.E. Radunz Appl. Microbiol. Biotechnol. 40 1993 382 385
- (1993) Appl. Microbiol. Biotechnol. , vol.40 , pp. 382-385
- Schwartz, H.¹ Licht, R.E.² Radunz, H.E.³

26
- 0032863086
- H. Pérez, H. Luna, N. Manjarerrez, A. Solis, and M. Nunez Biotechnol. Lett. 21 1999 855 858
- (1999) Biotechnol. Lett. , vol.21 , pp. 855-858
- Pérez, H.¹ Luna, H.² Manjarerrez, N.³ Solis, A.⁴ Nunez, M.⁵

27
- 0034781238
- N. Tarui, Y. Ikeura, H. Natsugari, and K. Nakahama J. Biosci. Bioeng. 92 2001 285 287
- (2001) J. Biosci. Bioeng. , vol.92 , pp. 285-287
- Tarui, N.¹ Ikeura, Y.² Natsugari, H.³ Nakahama, K.⁴

28
- 0036328027
- J.W. Wong, H.A. Watson, J.F. Bouressa, M.P. Burns, J.J. Cawley, A.E. Doro, D.B. Guzek, M.A. Hintz, E.L. McCormick, D.A. Scully, J.M. Siderewicz, W.J. Taylor, S.J. Truesdell, and R.G. Wax Org. Proc. Res. Dev. 6 2002 477 481
- (2002) Org. Proc. Res. Dev. , vol.6 , pp. 477-481
- Wong, J.W.¹ Watson, H.A.² Bouressa, J.F.³ Burns, M.P.⁴ Cawley, J.J.⁵ Doro, A.E.⁶ Guzek, D.B.⁷ Hintz, M.A.⁸ McCormick, E.L.⁹ Scully, D.A.¹⁰ Siderewicz, J.M.¹¹ Taylor, W.J.¹² Truesdell, S.J.¹³ Wax, R.G.¹⁴

29
- 78049320074
- Pfizer Products Inc. NY, USA
- M.S. Pacey Enzymatic Oxidation 2003 Pfizer Products Inc. NY, USA
- (2003) Enzymatic Oxidation
- Pacey, M.S.¹

30
- 4644231747
- D. Abanda-Nkpwatt, and W. Schwab J. Agric. Food Chem. 52 2004 5939 5942
- (2004) J. Agric. Food Chem. , vol.52 , pp. 5939-5942
- Abanda-Nkpwatt, D.¹ Schwab, W.²

31
- 0029918630
- H. Schwartz, A. Liebig-Weber, H. Hochstätter, and H. Böttcher Appl. Microbiol. Biotechnol. 44 1996 731 735
- (1996) Appl. Microbiol. Biotechnol. , vol.44 , pp. 731-735
- Schwartz, H.¹ Liebig-Weber, A.² Hochstätter, H.³ Böttcher, H.⁴

32
- 0022909196
- F.S. Sariaslani, and D.A. Kunz Biochem. Biophys. Res. Commun. 141 1986 405 410
- (1986) Biochem. Biophys. Res. Commun. , vol.141 , pp. 405-410
- Sariaslani, F.S.¹ Kunz, D.A.²

33
- 35148834294
- C. Mazier, M. Lombard, M.-A. Sari, and D. Buisson Biocatal. Biotransf. 25 2007 401 407
- (2007) Biocatal. Biotransf. , vol.25 , pp. 401-407
- Mazier, C.¹ Lombard, M.² Sari, M.-A.³ Buisson, D.⁴

34
- 34547118130
- Y.J. Chun, T. Shimada, R. Sanchez-Ponce, M.V. Martin, L. Lei, B. Zhao, S.L. Kelly, M.R. Waterman, D.C. Lamb, and F.P. Guengerich J. Biol. Chem. 282 2007 17486 17500
- (2007) J. Biol. Chem. , vol.282 , pp. 17486-17500
- Chun, Y.J.¹ Shimada, T.² Sanchez-Ponce, R.³ Martin, M.V.⁴ Lei, L.⁵ Zhao, B.⁶ Kelly, S.L.⁷ Waterman, M.R.⁸ Lamb, D.C.⁹ Guengerich, F.P.¹⁰

35
- 0032855263
- H. Ichinose, H. Wariishi, and H. Tanaka Biotechnol. Prog. 15 1999 706 714
- (1999) Biotechnol. Prog. , vol.15 , pp. 706-714
- Ichinose, H.¹ Wariishi, H.² Tanaka, H.³

36
- 33745942318
- K. Mitsukura, Y. Kondo, T. Yoshida, and T. Nagasawa Appl. Microbiol. Biotechnol. 71 2006 502 504
- (2006) Appl. Microbiol. Biotechnol. , vol.71 , pp. 502-504
- Mitsukura, K.¹ Kondo, Y.² Yoshida, T.³ Nagasawa, T.⁴

37
- 34547796330
- B. Kolvenbach, N. Schlaich, Z. Raoui, J. Prell, S. Zuhlke, A. Schaffer, F.P. Guengerich, and P.F.X. Corvini Appl. Environ. Microbiol. 73 2007 4776 4784
- (2007) Appl. Environ. Microbiol. , vol.73 , pp. 4776-4784
- Kolvenbach, B.¹ Schlaich, N.² Raoui, Z.³ Prell, J.⁴ Zuhlke, S.⁵ Schaffer, A.⁶ Guengerich, F.P.⁷ Corvini, P.F.X.⁸

38
- 55949092591
- R. Seshadri, A.S. Lamm, A. Khare, and J.P.N. Rosazza Enzyme Microb. Technol. 43 2008 486 494
- (2008) Enzyme Microb. Technol. , vol.43 , pp. 486-494
- Seshadri, R.¹ Lamm, A.S.² Khare, A.³ Rosazza, J.P.N.⁴

39
- 2042528492
- M. Sanchez-Gonzalez, and J.P.N. Rosazza J. Nat. Prod. 67 2004 553 558
- (2004) J. Nat. Prod. , vol.67 , pp. 553-558
- Sanchez-Gonzalez, M.¹ Rosazza, J.P.N.²

40
- 0033588164
- L.C. Bell-Parikh, and F.P. Guengerich J. Biol. Chem. 274 1999 23833 23840
- (1999) J. Biol. Chem. , vol.274 , pp. 23833-23840
- Bell-Parikh, L.C.¹ Guengerich, F.P.²

41
- 0025907945
- K. Watanabe, S. Narimatsu, I. Yamamoto, and H. Yoshimura J. Biol. Chem. 26 1991 2709 2711
- (1991) J. Biol. Chem. , vol.26 , pp. 2709-2711
- Watanabe, K.¹ Narimatsu, S.² Yamamoto, I.³ Yoshimura, H.⁴

42
- 33846234743
- D.C. Lamb, F.P. Guengerich, S.L. Kelly, and M.R. Waterman Expert Opin. Drug Metab. Toxicol. 2 2006 27 40
- (2006) Expert Opin. Drug Metab. Toxicol. , vol.2 , pp. 27-40
- Lamb, D.C.¹ Guengerich, F.P.² Kelly, S.L.³ Waterman, M.R.⁴

43
- 55049100842
- O. Pelkonen, M. Turpeinen, J. Hakkola, P. Honkakoski, J. Hukkanen, and H. Raunio Arch. Toxicol. 82 2008 667 715
- (2008) Arch. Toxicol. , vol.82 , pp. 667-715
- Pelkonen, O.¹ Turpeinen, M.² Hakkola, J.³ Honkakoski, P.⁴ Hukkanen, J.⁵ Raunio, H.⁶

44
- 0027168405
- C.H. Yun, R.A. Okerholm, and F.P. Guengerich Drug Metab. Disp. 21 1993 403 409
- (1993) Drug Metab. Disp. , vol.21 , pp. 403-409
- Yun, C.H.¹ Okerholm, R.A.² Guengerich, F.P.³

45
- 0031691414
- B.C. Jones, R. Hyland, M. Ackland, C.H. Tyman, and D.A. Smith Drug Metab. Disp. 29 1998 875 882
- (1998) Drug Metab. Disp. , vol.29 , pp. 875-882
- Jones, B.C.¹ Hyland, R.² Ackland, M.³ Tyman, C.H.⁴ Smith, D.A.⁵

46
- 0035570586
- H.L. George, and H.D. VanEtten Fungal Genet. Biol. 33 2001 37 48
- (2001) Fungal Genet. Biol. , vol.33 , pp. 37-48
- George, H.L.¹ Vanetten, H.D.²

47
- 34447323591
- D. Buisson, J. Quintin, and G. Lewin J. Nat. Prod. 70 2007 1035 1038
- (2007) J. Nat. Prod. , vol.70 , pp. 1035-1038
- Buisson, D.¹ Quintin, J.² Lewin, G.³

48
- 64649095590
- X.L. Xin, D.H. Su, X.J. Wang, and Q.P. Yuan J. Mol. Catal. B: Enzyme 59 2009 201 205
- (2009) J. Mol. Catal. B: Enzyme , vol.59 , pp. 201-205
- Xin, X.L.¹ Su, D.H.² Wang, X.J.³ Yuan, Q.P.⁴

49
- 0029040522
- K.H.J. Ling, G.A. Leeson, S.D. Burmaster, R.H. Hook, M.K. Reith, and L.K. Cheng Drug Metab. Disp. 23 1995 631 636
- (1995) Drug Metab. Disp. , vol.23 , pp. 631-636
- Ling, K.H.J.¹ Leeson, G.A.² Burmaster, S.D.³ Hook, R.H.⁴ Reith, M.K.⁵ Cheng, L.K.⁶

50
- 33751112296
- K.H. Liu, M.G. Kim, D.J. Lee, Y.J. Yoon, M.J. Kim, J.H. Shon, C.S. Choi, Y.K. Choi, Z. Desta, and J.G. Shin Drug Metab. Disp. 34 2006 1793 1797
- (2006) Drug Metab. Disp. , vol.34 , pp. 1793-1797
- Liu, K.H.¹ Kim, M.G.² Lee, D.J.³ Yoon, Y.J.⁴ Kim, M.J.⁵ Shon, J.H.⁶ Choi, C.S.⁷ Choi, Y.K.⁸ Desta, Z.⁹ Shin, J.G.¹⁰

51
- 0037025384
- D.C. Lamb, T. Skaug, H.L. Song, C.J. Jackson, L.M. Podust, M.R. Waterman, D.B. Kell, D.E. Kelly, and S.L. Kelly J. Biol. Chem. 277 2002 24000 24005
- (2002) J. Biol. Chem. , vol.277 , pp. 24000-24005
- Lamb, D.C.¹ Skaug, T.² Song, H.L.³ Jackson, C.J.⁴ Podust, L.M.⁵ Waterman, M.R.⁶ Kell, D.B.⁷ Kelly, D.E.⁸ Kelly, S.L.⁹

52
- 2142711569
- N. Parajuli, D.B. Basnet, H.C. Lee, J.K. Sohng, and K. Liou Arch. Biochem. Biophys. 425 2004 233 241
- (2004) Arch. Biochem. Biophys. , vol.425 , pp. 233-241
- Parajuli, N.¹ Basnet, D.B.² Lee, H.C.³ Sohng, J.K.⁴ Liou, K.⁵

53
- 0042672547
- D.C. Lamb, H. Ikeda, D.R. Nelson, J. Ishikawa, T. Skaug, C. Jackson, S. Omura, M.R. Waterman, and S.L. Kelly Biochem. Biophys. Res. Commun. 307 2003 610 619
- (2003) Biochem. Biophys. Res. Commun. , vol.307 , pp. 610-619
- Lamb, D.C.¹ Ikeda, H.² Nelson, D.R.³ Ishikawa, J.⁴ Skaug, T.⁵ Jackson, C.⁶ Omura, S.⁷ Waterman, M.R.⁸ Kelly, S.L.⁹

54
- 34548440174
- B. Zhao, and M.R. Waterman Drug. Metab. Rev. 39 2007 343 352
- (2007) Drug. Metab. Rev. , vol.39 , pp. 343-352
- Zhao, B.¹ Waterman, M.R.²

55
- 33749534302
- R. Quaderer, S. Omura, H. Ikeda, and D.E. Cane J. Am. Chem. Soc. 128 2006 13036 13037
- (2006) J. Am. Chem. Soc. , vol.128 , pp. 13036-13037
- Quaderer, R.¹ Omura, S.² Ikeda, H.³ Cane, D.E.⁴

56
- 34248642001
- Y.J. Chun, T. Shimada, M.R. Waterman, and F.P. Guengerich Biochem. Soc. Trans. 34 2006 1183 1185
- (2006) Biochem. Soc. Trans. , vol.34 , pp. 1183-1185
- Chun, Y.J.¹ Shimada, T.² Waterman, M.R.³ Guengerich, F.P.⁴

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