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Volumn 4, Issue 17, 2006, Pages 3303-3310

Synthesis of 1-β-O-acyl glucuronides of diclofenac, mefenamic acid and (S)-naproxen by the chemo-selective enzymatic removal of protecting groups from the corresponding methyl acetyl derivatives

(2) Baba, Akiko a Yoshioka, Tadao a

a HOKKAIDO INSTITUTE OF TECHNOLOGY (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BIOCHEMISTRY; CARBOXYLIC ACIDS; DERIVATIVES; ENZYMES; SYNTHESIS (CHEMICAL);

CHEMO SELECTIVE HYDROLYSES; MEFENAMIC ACID; METHYL ACETYL;

ORGANIC COMPOUNDS;

DICLOFENAC; GLUCURONIDE; MEFENAMIC ACID; NAPROXEN;

ACYLATION; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROLYSIS; KINETICS; METHYLATION; SYNTHESIS;

ACYLATION; CARBOHYDRATE CONFORMATION; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DICLOFENAC; GLUCURONIDES; HYDROLYSIS; KINETICS; MEFENAMIC ACID; METHYLATION; MODELS, MOLECULAR; NAPROXEN;

SUIDAE;

EID: 33747886887 PISSN: 14770520 EISSN: None Source Type: Journal
DOI: 10.1039/b608755h Document Type: Article

Times cited : (35)

References (50)

1
- 33747880535
- John Wiley & Sons, Chichester, England, ch. 8, pp. 163-214
- M. D. Coleman, in Human Drug Metabolism. An Introduction, John Wiley & Sons, Chichester, England, 2005, ch. 8, pp. 163-214
- (2005) Human Drug Metabolism. An Introduction
- Coleman In, M.D.¹

2
- 13844319935
- S. Zhou E. Chan W. Duan M. Huang Y.-Z. Chen Drug Metab. Rev. 2005 37 41 213
- (2005) Drug Metab. Rev. , vol.37 , pp. 41-213
- Zhou, S.¹ Chan, E.² Duan, W.³ Huang, M.⁴ Chen, Y.-Z.⁵

3
- 1642281756
- D. C. Evans A. P. Watt D. A. N. Griffith T. A. Baillie Chem. Res. Toxicol. 2004 17 3 16
- (2004) Chem. Res. Toxicol. , vol.17 , pp. 3-16
- Evans, D.C.¹ Watt, A.P.² Griffith, D.A.N.³ Baillie, T.A.⁴

4
- 0037304032
- S. A. Sheweita A. K. Tilmisany Curr. Drug Metab. 2003 4 45 58
- (2003) Curr. Drug Metab. , vol.4 , pp. 45-58
- Sheweita, S.A.¹ Tilmisany, A.K.²

5
- 0041342015
- W. M. Lee N. Engl. J. Med. 2003 349 474 485
- (2003) N. Engl. J. Med. , vol.349 , pp. 474-485
- Lee, W.M.¹

6
- 0030788713
- N. R. Pumford N. C. Halmes J. A. Hinson Drug Metab. Rev. 1997 29 39 57
- (1997) Drug Metab. Rev. , vol.29 , pp. 39-57
- Pumford, N.R.¹ Halmes, N.C.² Hinson, J.A.³

7
- 0023154139
- B. K. Park J. W. Coleman N. R. Kitteringham Biochem. Pharmacol. 1987 36 581 590
- (1987) Biochem. Pharmacol. , vol.36 , pp. 581-590
- Park, B.K.¹ Coleman, J.W.² Kitteringham, N.R.³

8
- 1642504441
- K. Sakaguchi M. Green N. Stock T. S. Reger J. Zunic C. King Arch. Biochem. Biophys. 2004 424 219 225
- (2004) Arch. Biochem. Biophys. , vol.424 , pp. 219-225
- Sakaguchi, K.¹ Green, M.² Stock, N.³ Reger, T.S.⁴ Zunic, J.⁵ King, C.⁶

9
- 0035038561
- C. King W. Tang J. Nugui T. Tephly M. Braun Toxicol. Sci. 2001 61 49 53
- (2001) Toxicol. Sci. , vol.61 , pp. 49-53
- King, C.¹ Tang, W.² Nugui, J.³ Tephly, T.⁴ Braun, M.⁵

10
- 33644841171
- J. H. Liu P. C. Smith Curr. Drug Metab. 2006 7 147 163
- (2006) Curr. Drug Metab. , vol.7 , pp. 147-163
- Liu, J.H.¹ Smith, P.C.²

11
- 0037422456
- M. J. Bailey R. G. Dickinson Chem.-Biol. Interact. 2003 145 117 137
- (2003) Chem.-Biol. Interact. , vol.145 , pp. 117-137
- Bailey, M.J.¹ Dickinson, R.G.²

12
- 0037306174
- M. Shipkova V. W. Armstrong M. Oellerich E. Wieland Ther. Drug Monit. 2003 25 1 16
- (2003) Ther. Drug Monit. , vol.25 , pp. 1-16
- Shipkova, M.¹ Armstrong, V.W.² Oellerich, M.³ Wieland, E.⁴

13
- 33747890101
- F. C. Kauffman, Springer-Verlag, Berlin, vol. 112, ch. 13, pp. 367-389
- C. Fenselau, in Conjugation-Deconjugation Reactions in Drug Metabolism and Toxicity, Handbook of Experimental Pharmacology, ed., F. C. Kauffman, Springer-Verlag, Berlin, 1994, vol. 112, ch. 13, pp. 367-389
- (1994) Conjugation-Deconjugation Reactions in Drug Metabolism and Toxicity, Handbook of Experimental Pharmacology, Ed.
- Fenselau In, C.¹

14
- 0026532030
- H. S. Langguth L. Z. Benet Drug Metab. Rev. 1992 24 5 48
- (1992) Drug Metab. Rev. , vol.24 , pp. 5-48
- Langguth, H.S.¹ Benet, L.Z.²

15
- 0021707968
- E. M. Faed Drug Metab. Rev. 1984 15 1213 1249
- (1984) Drug Metab. Rev. , vol.15 , pp. 1213-1249
- Faed, E.M.¹

16
- 0042591218
- W. Tang Curr. Drug Metab. 2003 4 319 329
- (2003) Curr. Drug Metab. , vol.4 , pp. 319-329
- Tang, W.¹

17
- 0142219774
- U. A. Boelsterli Toxicol. Appl. Pharmacol. 2003 192 307 322
- (2003) Toxicol. Appl. Pharmacol. , vol.192 , pp. 307-322
- Boelsterli, U.A.¹

18
- 0026737244
- H. K. Kroemer U. Klotz Clin. Pharmacokinet. 1992 23 292 310
- (1992) Clin. Pharmacokinet. , vol.23 , pp. 292-310
- Kroemer, H.K.¹ Klotz, U.²

19
- 0025116545
- P. C. Smith L. Z. Benet A. F. McDonagh Drug Metab. Dipos. 1990 18 639 644
- (1990) Drug Metab. Dipos. , vol.18 , pp. 639-644
- Smith, P.C.¹ Benet, L.Z.² McDonagh, A.F.³

20
- 0021847237
- Van Breeman C. F. Fenselau Drug Metab. Dispos. 1985 13 318 320
- (1985) Drug Metab. Dispos. , vol.13 , pp. 318-320
- Van Breeman¹ Fenselau, C.F.²

21
- 4644317079
- J. Wang M. Davis F. Li F. Azam J. Scatina R. Talaat Chem. Res. Toxicol. 2004 17 1206 1216
- (2004) Chem. Res. Toxicol. , vol.17 , pp. 1206-1216
- Wang, J.¹ Davis, M.² Li, F.³ Azam, F.⁴ Scatina, J.⁵ Talaat, R.⁶

22
- 10644294707
- S. J. Vanderhoeven J. Troke G. E. Tranter I. D. Wilson J. K. Nicholson J. C. Lindon Xenobiotica 2004 34 889 900
- (2004) Xenobiotica , vol.34 , pp. 889-900
- Vanderhoeven, S.J.¹ Troke, J.² Tranter, G.E.³ Wilson, I.D.⁴ Nicholson, J.K.⁵ Lindon, J.C.⁶

23
- 0442282104
- S. J. Vanderhoeven J. C. Lindon J. Troke G. E. Tranter I. D. Wilson J. K. Nicholson Xenobiotica 2004 34 73 85
- (2004) Xenobiotica , vol.34 , pp. 73-85
- Vanderhoeven, S.J.¹ Lindon, J.C.² Troke, J.³ Tranter, G.E.⁴ Wilson, I.D.⁵ Nicholson, J.K.⁶

24
- 0036206773
- S. Bolze N. Bromet C. G. -Feutry F. Massiere R. Boulieu T. Hulot Drug Metab. Dispos. 2002 30 404 413
- (2002) Drug Metab. Dispos. , vol.30 , pp. 404-413
- Bolze, S.¹ Bromet, N.² Feutry, C.G.³ Massiere, F.⁴ Boulieu, R.⁵ Hulot, T.⁶

25
- 0027199712
- L. Z. Benet H. S. Langguth S. Iwakawa C. Volland T. Mizuma S. Mayer E. Mutschler E. T. Lin Life Sci. 1993 53 141 146
- (1993) Life Sci. , vol.53 , pp. 141-146
- Benet, L.Z.¹ Langguth, H.S.² Iwakawa, S.³ Volland, C.⁴ Mizuma, T.⁵ Mayer, S.⁶ Mutschler, E.⁷ Lin, E.T.⁸

26
- 0037410072
- H. Kamimori Y. Ozaki Y. Okabayashi K. Ueno S. Narita Anal. Biochem. 2003 317 99 106
- (2003) Anal. Biochem. , vol.317 , pp. 99-106
- Kamimori, H.¹ Ozaki, Y.² Okabayashi, Y.³ Ueno, K.⁴ Narita, S.⁵

27
- 0034746532
- R. W. Mortensen O. Corcoran C. Cornett U. G. Sidelmann J. Troke J. C. Lindon J. K. Nicholson S. H. Hansen J. Pharm. Biomed. Anal. 2001 24 477 485
- (2001) J. Pharm. Biomed. Anal. , vol.24 , pp. 477-485
- Mortensen, R.W.¹ Corcoran, O.² Cornett, C.³ Sidelmann, U.G.⁴ Troke, J.⁵ Lindon, J.C.⁶ Nicholson, J.K.⁷ Hansen, S.H.⁸

28
- 0032826052
- T. Ebner G. Heinzel A. Prox K. Beschke H. Wachsmuth Drug Metab. Dispos. 1999 27 1143 1149
- (1999) Drug Metab. Dispos. , vol.27 , pp. 1143-1149
- Ebner, T.¹ Heinzel, G.² Prox, A.³ Beschke, K.⁴ Wachsmuth, H.⁵

29
- 0032055625
- J. Goto N. Murao J. Oohashi S. Ikegawa Steroids 1998 63 180 185
- (1998) Steroids , vol.63 , pp. 180-185
- Goto, J.¹ Murao, N.² Oohashi, J.³ Ikegawa, S.⁴

30
- 85077634689
- O. Mitsunobu Synthesis 1981 1 28
- (1981) Synthesis , pp. 1-28
- Mitsunobu, O.¹

31
- 0022636075
- R. R. Schmidt Angew. Chem., Int. Ed. Engl. 1986 25 212 235
- (1986) Angew. Chem., Int. Ed. Engl. , vol.25 , pp. 212-235
- Schmidt, R.R.¹

32
- 0028186224
- R. R. Schmidt W. Kinzy Adv. Carbohydr. Chem. Biochem. 1994 50 21 123
- (1994) Adv. Carbohydr. Chem. Biochem. , vol.50 , pp. 21-123
- Schmidt, R.R.¹ Kinzy, W.²

33
- 0029670688
- B. Becker A. B. Barua J. A. Olson Biochem. J. 1996 314 249 252
- (1996) Biochem. J. , vol.314 , pp. 249-252
- Becker, B.¹ Barua, A.B.² Olson, J.A.³

34
- 29844439969
- J. A. Perrie J. R. Harding D. W. Holt A. Johnston P. Meath A. V. Stachulski Org. Lett. 2005 13 2591 2594
- (2005) Org. Lett. , vol.13 , pp. 2591-2594
- Perrie, J.A.¹ Harding, J.R.² Holt, D.W.³ Johnston, A.⁴ Meath, P.⁵ Stachulski, A.V.⁶

35
- 0031550869
- H. Juteau Y. Gareau M. Labelle Tetrahedron Lett. 1997 38 1481 1484
- (1997) Tetrahedron Lett. , vol.38 , pp. 1481-1484
- Juteau, H.¹ Gareau, Y.² Labelle, M.³

36
- 11144303670
- P. J. Garregg Adv. Carbohydr. Chem. Biochem. 2004 59 69 134
- (2004) Adv. Carbohydr. Chem. Biochem. , vol.59 , pp. 69-134
- Garregg, P.J.¹

37
- 0003561055
- G.-J. Boons and K. J. Hale, Sheffield Academic Press, Sheffield, England, ch. 4, pp. 103-154
- J. Boons, in Organic Synthesis with Carbohydrates, ed., G.-J. Boons, and, K. J. Hale, 2000, Sheffield Academic Press, Sheffield, England, ch. 4, pp. 103-154
- (2000) Organic Synthesis with Carbohydrates, Ed.
- Boons In, J.¹

38
- 0037137196
- Y. Y. Root T. R. Wagner P. Norris Carbohydr. Res. 2002 337 2343 2346
- (2002) Carbohydr. Res. , vol.337 , pp. 2343-2346
- Root, Y.Y.¹ Wagner, T.R.² Norris, P.³

39
- 0034693114
- A. Trynda J. Madaj A. Konitz A. Wiśniewski Carbohydr. Res. 2000 329 249 252
- (2000) Carbohydr. Res. , vol.329 , pp. 249-252
- Trynda, A.¹ Madaj, J.² Konitz, A.³ Wiśniewski, A.⁴

40
- 0026603303
- H. Kunz R. Kullmann P. Wernig J. Zimmer Tetrahedron Lett. 1992 33 1969 1972
- (1992) Tetrahedron Lett. , vol.33 , pp. 1969-1972
- Kunz, H.¹ Kullmann, R.² Wernig, P.³ Zimmer, J.⁴

41
- 33747887313
- P. Singh L. L. Hingorani G. K. Trivedi Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1986 25 337 338
- (1986) Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. , vol.25 , pp. 337-338
- Singh, P.¹ Hingorani, L.L.² Trivedi, G.K.³

42
- 21044449003
- A. Akin T. T. Curran Synth. Commun. 2005 35 1649 1661
- (2005) Synth. Commun. , vol.35 , pp. 1649-1661
- Akin, A.¹ Curran, T.T.²

43
- 33747875867
- K. Drauz and H. Waldmann, Wiley-VCH, Weinheim, Germany, vol. 3, ch. 18, 1333-1417
- D. Kadereit, R. Reents, D. A. Jeyaraj and H. Waldman, in Enzyme Catalysis in Organic Synthesis, ed., K. Drauz, and, H. Waldmann, 2002, Wiley-VCH, Weinheim, Germany, vol. 3, ch. 18, 1333-1417
- (2002) Enzyme Catalysis in Organic Synthesis, Ed.
- Kadereit, D.¹ Reents, R.² Jeyaraj, D.A.³ Waldman In, H.⁴

44
- 0035498331
- D. Kadereit H. Waldmann Chem. Rev. 2001 101 3367 3396
- (2001) Chem. Rev. , vol.101 , pp. 3367-3396
- Kadereit, D.¹ Waldmann, H.²

45
- 0003610122
- U. T. Bornscheuer and R. J. Kazlauskas, Wiley-VCH, Weinheim, Germany, ch. 6, 131-172
- U. T. Bornscheuer and R. J. Kazlauskas, in Hydrolases in Organic Synthesis, ed., U. T. Bornscheuer, and, R. J. Kazlauskas, 1999, Wiley-VCH, Weinheim, Germany, ch. 6, 131-172
- (1999) Hydrolases in Organic Synthesis, Ed.
- Bornscheuer, U.T.¹ Kazlauskas In, R.J.²

46
- 0025903480
- D. G. Drueckhammer W. J. Hennen R. L. Pederson C. F. Barbas C. M. Gautheron T. Krach C.-H. Wong Synthesis 1991 499 525
- (1991) Synthesis , pp. 499-525
- Drueckhammer, D.G.¹ Hennen, W.J.² Pederson, R.L.³ Barbas, C.F.⁴ Gautheron, C.M.⁵ Krach, T.⁶ Wong, C.-H.⁷

47
- 0022400351
- A. Rachmel G. A. Hazelton A. L. Yergey D. J. Liberato Drug Metab. Dispos. 1985 13 705 710
- (1985) Drug Metab. Dispos. , vol.13 , pp. 705-710
- Rachmel, A.¹ Hazelton, G.A.² Yergey, A.L.³ Liberato, D.J.⁴

48
- 0019050007
- D. Farb W. P. Jencks Arch. Biochem. Biophys. 1980 203 214 226
- (1980) Arch. Biochem. Biophys. , vol.203 , pp. 214-226
- Farb, D.¹ Jencks, W.P.²

49
- 27444436638
- E. Barbayianni I. Fotakopoulou M. Schmidt V. C. Kokotou U. T. Bornscheuer G. Kokotos J. Org. Chem. 2005 70 8730 8733
- (2005) J. Org. Chem. , vol.70 , pp. 8730-8733
- Barbayianni, E.¹ Fotakopoulou, I.² Schmidt, M.³ Kokotou, V.C.⁴ Bornscheuer, U.T.⁵ Kokotos, G.⁶

50
- 33947461023
- G. N. Bollenback J. W. Long D. G. Benjamin J. A. Lindquist J. Am. Chem. Soc. 1955 77 3310 3315
- (1955) J. Am. Chem. Soc. , vol.77 , pp. 3310-3315
- Bollenback, G.N.¹ Long, J.W.² Benjamin, D.G.³ Lindquist, J.A.⁴

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