Laboratory Evolution of Robust and Enantioselective Baeyer−Villiger Monooxygenases for Asymmetric Catalysis

Manfred T. Reetz; Sheng Wu

doi:10.1021/ja906212k

journal article Oct 06, 2009

Laboratory Evolution of Robust and Enantioselective Baeyer−Villiger Monooxygenases for Asymmetric Catalysis

Manfred T. Reetz

Sheng Wu

Journal of the American Chemical Society Vol. 131 No. 42 pp. 15424-15432 · American Chemical Society (ACS)

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References

111

[1]

Reviews of Baeyer−Villiger reactions:

[2]

Krow G. R. Org. React. (N. Y.) (1993) 10.1002/0471264180.or043.03

[3]

Renz M. Org. Chem. (1999)

[4]

ten Brink G.-J. Chem. Rev. (2004) 10.1021/cr030011l

[5]

Bolm C. Angew. Chem. (1994) 10.1002/ange.19941061820

[6]

Angew. Chem., Int. Ed. Engl. (1994) 10.1002/anie.199418481

[7]

Gusso A. Organometallics (1994) 10.1021/om00021a019

[8]

Uchida T. Tetrahedron Lett. (2001) 10.1016/s0040-4039(01)01445-9

[9]

Ito K. Synlett (2003) 10.1055/s-2003-38377

[10]

Strukul G. Angew. Chem. (1998) 10.1002/(sici)1521-3757(19980504)110:9<1256::aid-ange1256>3.0.co;2-v

[11]

Angew. Chem., Int. Ed. (1998) 10.1002/(sici)1521-3773(19980518)37:9<1198::aid-anie1198>3.0.co;2-y

[12]

Frison J.-C. Tetrahedron (2006) 10.1016/j.tet.2005.12.080

[13]

Colladon M. Synlett (2006)

[14]

Murahashi S.-I. Angew. Chem. (2002) 10.1002/1521-3757(20020703)114:13<2472::aid-ange2472>3.0.co;2-b

[15]

Angew. Chem., Int. Ed. (2002) 10.1002/1521-3773(20020703)41:13<2366::aid-anie2366>3.0.co;2-s

[16]

Imada Y. Angew. Chem. (2005) 10.1002/ange.200462429

[17]

Angew. Chem., Int. Ed. (2005) 10.1002/anie.200462429

[18]

Wang B. J. Org. Chem. (2006) 10.1021/jo061341j

[19]

Peris G. Org. Lett. (2008) 10.1021/ol8010248

[20]

Malkov A. V. J. Org. Chem. (2008) 10.1021/jo800246g

[21]

Xu S. Angew. Chem. (2008) 10.1002/ange.200705932

[22]

Angew. Chem., Int. Ed. (2008) 10.1002/anie.200705932

[23]

Reviews of Baeyer-Villiger Monooxygenases as catalysts in organic chemistry(6):

[24]

Kayser M. M. Tetrahedron (2009) 10.1016/j.tet.2008.10.039

[25]

Stewart J. D. Curr. Org. Chem. (1998) 10.2174/1385272802666220128191443

[26]

cFlitsch, S. and Grogan, G.InEnzyme Catalysis in Organic Synthesis;Drauz, K. and Waldmann, H., Eds.Wiley-VCH:Weinheim, 2002; Vol.2, pp1202−1245.

[27]

Alphand V. Trends Biotechnol. (2003) 10.1016/s0167-7799(03)00144-6

[28]

Brzostowicz P. C. Appl. Environ. Microbiol. (2003) 10.1128/aem.69.1.334-342.2003

[29]

Mihovilovic M. D. Curr. Org. Chem (2006) 10.2174/138527206777698002

[30]

Wohlgemuth R. Eng. Life Sci. (2006) 10.1002/elsc.200620155

[31]

Kamerbeek N. M. Adv. Synth. Catal. (2003) 10.1002/adsc.200303014

[32]

Taschner M. J. J. Am. Chem. Soc. (1988) 10.1021/ja00228a053

[33]

Taschner M. J. Tetrahedron: Asymmetry (1993) 10.1016/s0957-4166(00)80248-7

[34]

Taschner M. J. J. Chem. Soc., Chem. Commun. (1992) 10.1039/c39920001384

[35]

Isolation, characterization and/or mechanistic studies of CHMOs and other BVMOs:

[36]

Turfitt G. E. Biochem. J. (1948) 10.1042/bj0420376

[37]

Donoghue N. A. Eur. J. Biochem. (1976) 10.1111/j.1432-1033.1976.tb10220.x

[38]

Schwab J. M. J. Am. Chem. Soc. (1983) 10.1021/ja00352a044

[39]

Walsh C. T. Angew. Chem. (1988) 10.1002/ange.19881000305

[40]

Angew. Chem., Int. Ed. Engl. (1988) 10.1002/anie.198803331

[41]

Brzostowicz P. C. Appl. Environ. Microbiol. (2003) 10.1128/aem.69.1.334-342.2003

[42]

Sheng D. Biochemistry (2001) 10.1021/bi011153h

[43]

Zhao H. Curr. Opin. Biotechnol. (2003) 10.1016/j.copbio.2003.09.007

[44]

van der Donk W. A. Curr. Opin. Biotechnol. (2003) 10.1016/s0958-1669(03)00094-6

[45]

de Gonzalo G. Chem. Commun. (Cambridge, U. K.) (2005) 10.1039/b504921k

[46]

Hollmann F. Angew. Chem. (2007) 10.1002/ange.200605169

[47]

Angew. Chem., Int. Ed. (2007) 10.1002/anie.200605169

[48]

Hollmann F. Trends Biotechnol. (2006) 10.1016/j.tibtech.2006.02.003

[49]

Urlacher V. B. Curr. Opin. Chem. Biol. (2006) 10.1016/j.cbpa.2006.02.001

[50]

Zambianchi F. Biotechnol. Bioeng. (2002) 10.1002/bit.10207

Showing 50 of 111 references

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Details

Published: Oct 06, 2009
Vol/Issue: 131(42)
Pages: 15424-15432

Authors

M

Manfred T. Reetz

Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, 45470 Mülheim an der Ruhr, Germany

S

Sheng Wu

Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, 45470 Mülheim an der Ruhr, Germany

Cite This Article

Manfred T. Reetz, Sheng Wu (2009). Laboratory Evolution of Robust and Enantioselective Baeyer−Villiger Monooxygenases for Asymmetric Catalysis. Journal of the American Chemical Society, 131(42), 15424-15432. https://doi.org/10.1021/ja906212k

Laboratory Evolution of Robust and Enantioselective Baeyer−Villiger Monooxygenases for Asymmetric Catalysis

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