SCOPUS 정보 검색 플랫폼

Volumn 352, Issue 14-15, 2010, Pages 2663-2666

Asymmetric synthesis of (R)-3-hydroxy-2-methylpropanoate ('Roche Ester') and derivatives via biocatalytic C=C-bond reduction

(4) Stueckler, Clemens a Winkler, Christoph K a Bonnekessel, Melanie b Faber, Kurt a

a UNIVERSITY OF GRAZ (Austria)

b BASF SE (Germany)

Author keywords

biocatalysis; C=C bioreduction; enoate reductase; old yellow enzyme; substrate engineering

Indexed keywords

EID: 78349285477 PISSN: 16154150 EISSN: 16154169 Source Type: Journal
DOI: 10.1002/adsc.201000522 Document Type: Article

Times cited : (59)

References (55)

1
- 0035987236
- R. E. Williams, N. C. Bruce, 2002, 148, 1607 - 1614
- R. E. Williams, N. C. Bruce, 2002, 148, 1607 - 1614.

2
- 34047189417
- R. Stuermer, B. Hauer, M. Hall, K. Faber, Curr. Opin. Chem. Biol. 2007, 11, 203 - 213.
- (2007) Curr. Opin. Chem. Biol. , vol.11 , pp. 203-213
- Stuermer, R.¹ Hauer, B.² Hall, M.³ Faber, K.⁴

3
- 0000939067
- O. Warburg, W. Christian, Biochem. Z. 1933, 266, 377 - 411.
- (1933) Biochem. Z. , vol.266 , pp. 377-411
- Warburg, O.¹ Christian, W.²

4
- 77149145484
- N. J. Mueller, C. Stueckler, B. Hauer, N. Baudendistel, H. Housden, N. C. Bruce, K. Faber, Adv. Synth. Catal. 2010, 352, 387 - 394
- (2010) Adv. Synth. Catal. , vol.352 , pp. 387-394
- Mueller, N.J.¹ Stueckler, C.² Hauer, B.³ Baudendistel, N.⁴ Housden, H.⁵ Bruce, N.C.⁶ Faber, K.⁷

5
- 72149102108
- A. Fryszkowska, H. Toogood, M. Sakuma, J. M. Gardiner, G. M. Stephens, N. S. Scrutton, Adv. Synth. Catal. 2009, 351, 2976 - 2990
- (2009) Adv. Synth. Catal. , vol.351 , pp. 2976-2990
- Fryszkowska, A.¹ Toogood, H.² Sakuma, M.³ Gardiner, J.M.⁴ Stephens, G.M.⁵ Scrutton, N.S.⁶

6
- 73349113954
- D. J. Bougioukou, S. Kille, A. Taglieber, M. T. Reetz, Adv. Synth. Catal. 2009, 351, 3287 - 3305.
- (2009) Adv. Synth. Catal. , vol.351 , pp. 3287-3305
- Bougioukou, D.J.¹ Kille, S.² Taglieber, A.³ Reetz, M.T.⁴

7
- 53849113495
- M. Hall, C. Stueckler, W. Kroutil, P. Macheroux, K. Faber, Angew. Chem. 2007, 119, 4008 - 4011
- (2007) Angew. Chem. , vol.119 , pp. 4008-4011
- Hall, M.¹ Stueckler, C.² Kroutil, W.³ MacHeroux, P.⁴ Faber, K.⁵

8
- 34250782749
- Angew. Chem. Int. Ed. 2007, 46, 3934 - 3937
- (2007) Angew. Chem. Int. Ed. , vol.46 , pp. 3934-3937

9
- 51849169218
- M. Hall, C. Stueckler, H. Ehammer, E. Pointner, G. Oberdorfer, K. Gruber, B. Hauer, R. Stuermer, W. Kroutil, P. Macheroux, K. Faber, Adv. Synth. Catal. 2008, 350, 411 - 418
- (2008) Adv. Synth. Catal. , vol.350 , pp. 411-418
- Hall, M.¹ Stueckler, C.² Ehammer, H.³ Pointner, E.⁴ Oberdorfer, G.⁵ Gruber, K.⁶ Hauer, B.⁷ Stuermer, R.⁸ Kroutil, W.⁹ MacHeroux, P.¹⁰ Faber, K.¹¹

10
- 53849094459
- M. Hall, C. Stueckler, B. Hauer, R. Stuermer, T. Friedrich, M. Breuer, W. Kroutil, K. Faber, Eur. J. Org. Chem. 2008, 1511 - 1516
- (2008) Eur. J. Org. Chem. , pp. 1511-1516
- Hall, M.¹ Stueckler, C.² Hauer, B.³ Stuermer, R.⁴ Friedrich, T.⁵ Breuer, M.⁶ Kroutil, W.⁷ Faber, K.⁸

11
- 46449101665
- B. Kosjek, F. J. Fleitz, P. G. Dormer, J. T. Kuethe, P. N. Devine, Tetrahedron: Asymmetry 2008, 19, 1403 - 1406
- (2008) Tetrahedron: Asymmetry , vol.19 , pp. 1403-1406
- Kosjek, B.¹ Fleitz, F.J.² Dormer, P.G.³ Kuethe, J.T.⁴ Devine, P.N.⁵

12
- 38349186682
- C. Stueckler, M. Hall, H. Ehammer, E. Pointner, W. Kroutil, P. Macheroux, K. Faber, Org. Lett, 2007, 9, 5409 - 5411
- (2007) Org. Lett , vol.9 , pp. 5409-5411
- Stueckler, C.¹ Hall, M.² Ehammer, H.³ Pointner, E.⁴ Kroutil, W.⁵ MacHeroux, P.⁶ Faber, K.⁷

13
- 77956316535
- C. Stueckler, N. J. Mueller, C. K. Winkler, S. M. Glueck, K. Gruber, G. Steinkellner K. Faber, Dalton Trans. 2010, 39, 8472 - 8476.
- (2010) Dalton Trans. , vol.39 , pp. 8472-8476
- Stueckler, C.¹ Mueller, N.J.² Winkler, C.K.³ Glueck, S.M.⁴ Gruber, K.⁵ Faber, G.S.K.⁶

14
- 0017084882
- N. Cohen, W. F. Eichel, R. J. Lopersti, C. Neukom, G. Saucy, J. Org. Chem. 1976, 41, 3505 - 3511.
- (1976) J. Org. Chem. , vol.41 , pp. 3505-3511
- Cohen, N.¹ Eichel, W.F.² Lopersti, R.J.³ Neukom, C.⁴ Saucy, G.⁵

15
- 84963184494
- Q. Branca, A. Fischli, Helv. Chim. Acta 1977, 60, 925 - 944.
- (1977) Helv. Chim. Acta , vol.60 , pp. 925-944
- Branca, Q.¹ Fischli, A.²

16
- 0001010896
- D. A. Evans, C. E. Sacks, W. A. Kleschick, T. R. Taber, J. Am. Chem. Soc. 1979, 101, 6789 - 6791.
- (1979) J. Am. Chem. Soc. , vol.101 , pp. 6789-6791
- Evans, D.A.¹ Sacks, C.E.² Kleschick, W.A.³ Taber, T.R.⁴

17
- 66449116373
- M. Pérez, D. I. Pérez, A. Martínez, A. Castrol, G. Gómez, Y. Fall, Chem. Commun. 2009, 3252 - 3254.
- (2009) Chem. Commun. , pp. 3252-3254
- Pérez, M.¹ Pérez, D.I.² Martínez, A.³ Castrol, A.⁴ Gómez, G.⁵ Fall, Y.⁶

18
- 62349091154
- S. V. Ley, M. N. Tackett, M. L. Maddess, J. C. Anderson, P. E. Brennan, M. W. Cappi, J. P. Heer, C. Helgen, M. Kori, C. Kouklovsky, S. P. Marsden, J. Norman, D. P. Osborn, M. Á. Palomero, J. B. J. Pavey, C. Pinel, L. A. Robinson, J. Schnaubelt, J. S. Scott, C. D. Spilling, H. Watanabe, K. E. Wesson, M. C. Willis, Chem. Eur. J. 2009, 15, 2874 - 2914.
- (2009) Chem. Eur. J. , vol.15 , pp. 2874-2914
- Ley, S.V.¹ Tackett, M.N.² Maddess, M.L.³ Anderson, J.C.⁴ Brennan, P.E.⁵ Cappi, M.W.⁶ Heer, J.P.⁷ Helgen, C.⁸ Kori, M.⁹ Kouklovsky, C.¹⁰ Marsden, S.P.¹¹ Norman, J.¹² Osborn, D.P.¹³ Palomero, M.Á.¹⁴ Pavey, J.B.J.¹⁵ Pinel, C.¹⁶ Robinson, L.A.¹⁷ Schnaubelt, J.¹⁸ Scott, J.S.¹⁹ Spilling, C.D.²⁰ more..

19
- 4344626586
- A. B. Smith III, C. M. Adams, S. A. Lodise Barbosa, A. P. Degnan, Proc. Natl. Acad. Sci. USA 2004, 101, 12042 - 12047.
- (2004) Proc. Natl. Acad. Sci. USA , vol.101 , pp. 12042-12047
- Iii, A.B.S.¹ Adams, C.M.² Barbosa, S.A.L.³ Degnan, A.P.⁴

20
- 5344237662
- Y. Shin, J.-H. Fournier, Y. Fukui, A. M. Brückner, D. P. Curran, Angew. Chem. 2004, 116, 4734 - 4737
- (2004) Angew. Chem. , vol.116 , pp. 4734-4737
- Shin, Y.¹ Fournier, J.-H.² Fukui, Y.³ Brückner, A.M.⁴ Curran, D.P.⁵

21
- 5344247972
- Angew. Chem. Int. Ed. 2004, 43, 4634 - 4637.
- (2004) Angew. Chem. Int. Ed. , vol.43 , pp. 4634-4637

22
- 33746407220
- J. E. D. Kirkham, V. Lee, J. E. Baldwin, Chem. Commun. 2006, 2863 - 2865.
- (2006) Chem. Commun. , pp. 2863-2865
- Kirkham, J.E.D.¹ Lee, V.² Baldwin, J.E.³

23
- 0002450059
- C. H. Senanayake, R. D. Larsen, T. J. Bill, J. Liu, E. G. Corley, P. J. Reider, Synlett 1994, 199 - 200.
- (1994) Synlett , pp. 199-200
- Senanayake, C.H.¹ Larsen, R.D.² Bill, T.J.³ Liu, J.⁴ Corley, E.G.⁵ Reider, P.J.⁶

24
- 37049069877
- B. A. Czeskis, A. M. Moissenkov, J. Chem. Soc. Perkin Trans. 1 1989, 1353 - 1354.
- (1989) J. Chem. Soc. Perkin Trans. 1 , pp. 1353-1354
- Czeskis, B.A.¹ Moissenkov, A.M.²

25
- 4243116083
- W. Choy, P. Ma, S. Masamune, Tetrahedron Lett. 1981, 22, 3555 - 3556.
- (1981) Tetrahedron Lett. , vol.22 , pp. 3555-3556
- Choy, W.¹ Ma, P.² Masamune, S.³

26
- 61649087622
- M. Qui, D.-Y. Wang, X.-P. Hu, J.-D. Huang, S.-B. Yu, J. Deng, Z.-C. Duan, Z. Zheng, Tetrahedron: Asymmetry 2009, 20, 210 - 213
- (2009) Tetrahedron: Asymmetry , vol.20 , pp. 210-213
- Qui, M.¹ Wang, D.-Y.² Hu, X.-P.³ Huang, J.-D.⁴ Yu, S.-B.⁵ Deng, J.⁶ Duan, Z.-C.⁷ Zheng, Z.⁸

27
- 56649095989
- J. Holz, B. Schäffner, O. Zayas, A. Spannenberg, A. Börner, Adv. Synth. Catal. 2008, 350, 2533 - 2543
- (2008) Adv. Synth. Catal. , vol.350 , pp. 2533-2543
- Holz, J.¹ Schäffner, B.² Zayas, O.³ Spannenberg, A.⁴ Börner, A.⁵

28
- 49049096215
- J. Wassenaar, M. Kuil, J. N. H. Reek, Adv. Synth. Catal. 2008, 350, 1610 - 1614
- (2008) Adv. Synth. Catal. , vol.350 , pp. 1610-1614
- Wassenaar, J.¹ Kuil, M.² Reek, J.N.H.³

29
- 0041749668
- H. Shimizu, T. Saito, H. Kumobayashi, Adv. Synth. Catal. 2003, 345, 185 - 189.
- (2003) Adv. Synth. Catal. , vol.345 , pp. 185-189
- Shimizu, H.¹ Saito, T.² Kumobayashi, H.³

30
- 56649094542
- C. Pautigny, S. Jeulin, T. Ayad, Z. Zhang, J.-P. Genêt, V. Ratovelomanana-Vidal, Adv. Synth. Catal. 2008, 350, 2525 - 2532
- (2008) Adv. Synth. Catal. , vol.350 , pp. 2525-2532
- Pautigny, C.¹ Jeulin, S.² Ayad, T.³ Zhang, Z.⁴ Genêt, J.-P.⁵ Ratovelomanana-Vidal, V.⁶

31
- 34547236581
- S. Jeulin, T. Ayad, V. Ratovelomanana-Vidal, J. P. Genêt, Adv. Synth. Catal. 2007, 349, 1592 - 1596.
- (2007) Adv. Synth. Catal. , vol.349 , pp. 1592-1596
- Jeulin, S.¹ Ayad, T.² Ratovelomanana-Vidal, V.³ Genêt, J.P.⁴

32
- 0001466526
- H. Ohta, H. Tetsukawa, N. Noto, J. Org. Chem. 1982, 47, 2400 - 2404
- (1982) J. Org. Chem. , vol.47 , pp. 2400-2404
- Ohta, H.¹ Tetsukawa, H.² Noto, N.³

33
- 0038498492
- F. Molinari, R. Gandolfi, R. Villa, E. Urban, A. Kiener, Tetrahedron: Asymmetry 2003, 14, 2041 - 2043.
- (2003) Tetrahedron: Asymmetry , vol.14 , pp. 2041-2043
- Molinari, F.¹ Gandolfi, R.² Villa, R.³ Urban, E.⁴ Kiener, A.⁵

34
- 0018347070
- H. G. W. Leuenberger, W. Boguth, R. Barner, M. Schmid, R. Zell, Helv. Chim. Acta 1979, 62, 455 - 463.
- (1979) Helv. Chim. Acta , vol.62 , pp. 455-463
- Leuenberger, H.G.W.¹ Boguth, W.² Barner, R.³ Schmid, M.⁴ Zell, R.⁵

35
- 0015032644
- C. T. Goodhue, J. R. Schaeffer, Biotechnol. Bioeng. 1971, 203 - 214
- (1971) Biotechnol. Bioeng. , pp. 203-214
- Goodhue, C.T.¹ Schaeffer, J.R.²

36
- 78349270668
- (Eds.: A. N. Collins, G. N. Sheldrake, J. Crosby), Wiley, New York,; this biotransformation was shown to proceed via the fatty acid β-oxidation pathway, that is, (i) dehydrogenation to furnish methacrylate, which undergoes (ii) asymmetric addition of water across the acyl-CoA-activated C=C-bond in a subsequent step; see
- T. Ohashi, J. Hasegawa, New preparative methods for optically active β-hydroxycarboxylic acids, in: Chirality in Industry, (Eds.:, A. N. Collins, G. N. Sheldrake, J. Crosby,), Wiley, New York, 1992, pp. 249 - 267; this biotransformation was shown to proceed via the fatty acid β-oxidation pathway, that is, (i) dehydrogenation to furnish methacrylate, which undergoes (ii) asymmetric addition of water across the acyl-CoA-activated C=C-bond in a subsequent step; see
- (1992) New Preparative Methods for Optically Active β-hydroxycarboxylic Acids, In: Chirality in Industry , pp. 249-267
- Ohashi, T.¹ Hasegawa, J.²

37
- 0017388480
- D. J. Aberhart, Bioorg. Chem. 1977, 6, 191 - 201.
- (1977) Bioorg. Chem. , vol.6 , pp. 191-201
- Aberhart, D.J.¹

38
- 72149111396
- E. Burda, M. Kraußer, G. Fischer, W. Hummel, F. Müller-Uri, W. Kreis, H. Gröger, Adv. Synth. Catal. 2009, 351, 2787 - 2790.
- (2009) Adv. Synth. Catal. , vol.351 , pp. 2787-2790
- Burda, E.¹ Kraußer, M.² Fischer, G.³ Hummel, W.⁴ Müller-Uri, F.⁵ Kreis, W.⁶ Gröger, H.⁷

39
- 0025718748
- K. Saito, D. J. Thiele, M. Davio, O. Lockridge, V. Massey, J. Biol. Chem. 1991, 266, 20720 - 20724
- (1991) J. Biol. Chem. , vol.266 , pp. 20720-20724
- Saito, K.¹ Thiele, D.J.² Davio, M.³ Lockridge, O.⁴ Massey, V.⁵

40
- 0027401725
- K. Stott, K. Saito, D. J. Thiele, V. Massey, J. Biol. Chem. 1993, 268, 6097 - 6106
- (1993) J. Biol. Chem. , vol.268 , pp. 6097-6106
- Stott, K.¹ Saito, K.² Thiele, D.J.³ Massey, V.⁴

41
- 0028963408
- Y. S. Niino, S. Chakraborty, B. J. Brown, V. Massey, J. Biol. Chem. 1995, 270, 1983 - 1991.
- (1995) J. Biol. Chem. , vol.270 , pp. 1983-1991
- Niino, Y.S.¹ Chakraborty, S.² Brown, B.J.³ Massey, V.⁴

42
- 33749246399
- C. Breithaupt, R. Kurzbauer, H. Lilie, A. Schaller, J. Strassner, R. Huber, P. Macheroux, T. Clausen, Proc. Natl. Acad. Sci. USA 2006, 103, 14337 - 14342.
- (2006) Proc. Natl. Acad. Sci. USA , vol.103 , pp. 14337-14342
- Breithaupt, C.¹ Kurzbauer, R.² Lilie, H.³ Schaller, A.⁴ Strassner, J.⁵ Huber, R.⁶ MacHeroux, P.⁷ Clausen, T.⁸

43
- 23044455760
- K. Kitzing, T. B. Fitzpatrick, C. Wilken, J. Sawa, G. P. Bourenkov, P. Macheroux, T. Clausen, J. Biol. Chem. 2005, 280, 27904 - 27913.
- (2005) J. Biol. Chem. , vol.280 , pp. 27904-27913
- Kitzing, K.¹ Fitzpatrick, T.B.² Wilken, C.³ Sawa, J.⁴ Bourenkov, G.P.⁵ MacHeroux, P.⁶ Clausen, T.⁷

44
- 34548240307
- A. Müller, B. Hauer, B. Roche, Biotechnol. Bioeng, 2007, 98, 22 - 29.
- (2007) Biotechnol. Bioeng , vol.98 , pp. 22-29
- Müller, A.¹ Hauer, B.² Roche, B.³

45
- 38949213661
- R. M. Wittich, A. Haidour, P. van Dillewijn, J. L. Ramos, Environ. Sci. Technol, 2008, 42, 734 - 739
- (2008) Environ. Sci. Technol , vol.42 , pp. 734-739
- Wittich, R.M.¹ Haidour, A.² Van Dillewijn, P.³ Ramos, J.L.⁴

46
- 33745879474
- J. J. Griese, R. P. Jakob, S. Schwarzinger, H. Dobbek, J. Mol. Biol. 2006, 361, 140 - 152
- (2006) J. Mol. Biol. , vol.361 , pp. 140-152
- Griese, J.J.¹ Jakob, R.P.² Schwarzinger, S.³ Dobbek, H.⁴

47
- 34547162526
- J. F. Chaparro-Riggers, T. A. Rogers, E. Vazquez-Figueroa, K. M. Polizzi, A. S. Bommarius, Adv. Synth. Catal. 2007, 349, 1521 - 1531.
- (2007) Adv. Synth. Catal. , vol.349 , pp. 1521-1531
- Chaparro-Riggers, J.F.¹ Rogers, T.A.² Vazquez-Figueroa, E.³ Polizzi, K.M.⁴ Bommarius, A.S.⁵

48
- 0030867134
- J. R. Snape, N. A. Walkley, A. P. Morby, S. Nicklin, G. F. White, J. Bacteriol. 1997, 179, 7796 - 7802
- (1997) J. Bacteriol. , vol.179 , pp. 7796-7802
- Snape, J.R.¹ Walkley, N.A.² Morby, A.P.³ Nicklin, S.⁴ White, G.F.⁵

49
- 0030039535
- G. F. White, J. R. Snape, S. Nicklin, Appl. Environ. Microbiol. 1996, 62, 637 - 642.
- (1996) Appl. Environ. Microbiol. , vol.62 , pp. 637-642
- White, G.F.¹ Snape, J.R.² Nicklin, S.³

50
- 0032491154
- J. Buckman, S. M. Miller, Biochemistry 1998, 37, 14326 - 14336.
- (1998) Biochemistry , vol.37 , pp. 14326-14336
- Buckman, J.¹ Miller, S.M.²

51
- 0025718748
- K. Saito, D. J. Thiele, M. Davio, O. Lockridge, V. Massey, J. Biol. Chem. 1991, 266, 20720 - 20724
- (1991) J. Biol. Chem. , vol.266 , pp. 20720-20724
- Saito, K.¹ Thiele, D.J.² Davio, M.³ Lockridge, O.⁴ Massey, V.⁵

52
- 0027401725
- K. Stott, K. Saito, D. J. Thiele, V. Massey, J. Biol. Chem. 1993, 268, 6097 - 6106
- (1993) J. Biol. Chem. , vol.268 , pp. 6097-6106
- Stott, K.¹ Saito, K.² Thiele, D.J.³ Massey, V.⁴

53
- 0028963408
- Y. S. Niino, S. Chakraborty, B. J. Brown, V. Massey, J. Biol. Chem. 1995, 270, 1983 - 1991.
- (1995) J. Biol. Chem. , vol.270 , pp. 1983-1991
- Niino, Y.S.¹ Chakraborty, S.² Brown, B.J.³ Massey, V.⁴

54
- 77950570908
- K. Durchschein, B. Ferreira-da Silva, S. Wallner, P. Macheroux, W. Kroutil, S. M. Glueck, K. Faber, Green Chem. 2010, 12, 616 - 619.
- (2010) Green Chem. , vol.12 , pp. 616-619
- Durchschein, K.¹ Silva, B.F.² Wallner, S.³ MacHeroux, P.⁴ Kroutil, W.⁵ Glueck, S.M.⁶ Faber, K.⁷

55
- 85026873969
- K. W. C. Poon, P. A. Albiniak, G. B. Dudley, Org. Synth. 2007, 84, 295 - 299.
- (2007) Org. Synth. , vol.84 , pp. 295-299
- Poon, K.W.C.¹ Albiniak, P.A.² Dudley, G.B.³

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.