Upgrading Nature’s Tools: Expression Enhancement and Preparative Utility of the Halogenase RebH

James T. Payne; Jared C. Lewis

doi:10.1055/s-0033-1341024

Synlett, Inhaltsverzeichnis

Synlett 2014; 25(10): 1345-1349
DOI: 10.1055/s-0033-1341024

synpacts

Upgrading Nature’s Tools: Expression Enhancement and Preparative Utility of the Halogenase RebH

James T. Payne

Department of Chemistry, University of Chicago, Chicago, IL 60637, USA Fax: +1(773)7020805 eMail: jaredlewis@uchicago.edu

,

Jared C. Lewis*

Department of Chemistry, University of Chicago, Chicago, IL 60637, USA Fax: +1(773)7020805 eMail: jaredlewis@uchicago.edu

› Institutsangaben

Abstract

Alle Artikel dieser Rubrik

Abstract

Enzymes often excel at performing green, selective chemical reactions, and thus offer key advantages over many chemocatalytic processes. We recently reported the enhanced expression of a regioselective halogenase, RebH, in E. coli, as well as its use in the preparative halogenation of a range of substrates. These improvements have made it possible to begin directed evolution to improve further the activity and substrate scope of RebH. Chemistry is in need of a regioselective halogenation catalyst, and this work illustrates the potential and recent gains made towards using enzymes for this goal.

Key words

halogenation - catalysis - enzymes - directed evolution - protein engineering

Volltext

Referenzen

References and Notes

1a Gribble GW. J. Chem. Educ. 2004; 81: 1441
1b Gribble GW. Chemosphere 2003; 52: 289

2 Herrera-Rodriguez LN, Khan F, Robins KT, Meyer H.-P. Chem. Today 2011; 29: 31
3 Suzuki A. J. Organomet. Chem. 1999; 576: 147
4 Wipf P, Lim S. J. Am. Chem. Soc. 1995; 117: 558
5 Garg NK, Caspi DD, Stoltz BM. J. Am. Chem. Soc. 2004; 126: 9552
6 Anderson BA, Becke LM, Booher RN, Flaugh ME, Harn NK, Kress TJ, Varie DL, Wepsiec JP. J. Org. Chem. 1997; 62: 8634

7a Bunders CA, Minvielle MJ, Worthington RJ, Ortiz M, Cavanagh J, Melander C. J. Am. Chem. Soc. 2011; 133: 20160
7b Sims JJ, Donnell MS, Leary JV, Lacy GH. Antimicrob. Agents Chemother. 1975; 7: 320

8 Degterev A, Hitomi J, Germscheid M, Ch’en IL, Korkina O, Teng X, Abbott D, Cuny GD, Yuan C, Wagner G, Hedrick SM, Gerber SA, Lugovskoy A, Yuan J. Nat. Chem. Biol. 2008; 4: 313
9 Smith BM, Smith JM, Tsai JH, Schultz JA, Gilson CA, Estrada SA, Chen RR, Park DM, Prieto EB, Gallardo CS, Sengupta D, Dosa PI, Covel JA, Ren A, Webb RR, Beeley NR. A, Martin M, Morgan M, Espitia S, Saldana HR, Bjenning C, Whelan KT, Grottick AJ, Menzaghi F, Thomsen WJ. J. Med. Chem. 2008; 51: 305
10 Sun H, Keefer CE, Scott DO. Drug Metab. Lett. 2011; 5: 232
11 Sasson Y. Formation of Carbon-Halogen Bonds (Cl, Br, I). In Patai’s Chemistry of Functional Groups. Wiley–VCH; Weinheim: 2009
12 Smith K, El-Hiti GA. Curr. Org. Synth. 2004; 1: 253-274
13 Podgoršek A, Zupan M, Iskra J. Angew. Chem. Int. Ed. 2009; 48: 8424
14 Robbins DW, Boebel TA, Hartwig JF. J. Am. Chem. Soc. 2010; 132: 4068

15a Vaillancourt FH, Yeh E, Vosburg DA, Garneau-Tsodikova S, Walsh CT. Chem. Rev. 2006; 106: 3364
15b Butler A, Sandy M. Nature 2009; 460: 848

16 van Pée K.-H, Patallo EP. Appl. Microbiol. Biotechnol. 2006; 70: 631
17 Yeh E, Blasiak LC, Koglin A, Drennan CL, Walsh CT. Biochemistry 2007; 46: 1284
18 Woodley J. Trends Biotechnol. 2008; 26: 321

For recent reviews, see:

19a Shivange A, Marienhagen J, Mundhada H, Schenk A, Schwaneberg U. Curr. Opin. Chem. Biol. 2009; 13: 19
19b Bommarius A, Blum J, Abrahamson M. Curr. Opin. Chem. Biol. 2011; 15: 194
19c Romero P, Arnold F. Nat. Rev. Mol. Cell Biol. 2009; 10: 866

20 Keller S, Wage T, Hohaus K, Hӧlzer M, Eichhorn E, van Pée K.-H. Angew. Chem. Int. Ed. 2000; 39: 2300
21 Yeh E, Garneau S, Walsh CT. Proc. Natl. Acad. Sci. U.S.A. 2005; 102: 3960
22 Roy AB, Grüschow S, Cairns N, Goss RJ. M. J. Am. Chem. Soc. 2010; 132: 12243
23 Hӧlzer M, Burd W, Reissig H.-U, van Pée K.-H. Adv. Synth. Catal. 2001; 343: 591
24 Runguphan W, Qu X, O’Connor SE. Nature 2010; 468: 461
25 Glenn WS, Nims E, O’Connor SE. J. Am. Chem. Soc. 2011; 133: 19346
26 Mayhew M, da Silva AC. R, Martin J, Erdjument-Bromage H, Tempst P, Hartl FU. Nature 1996; 379: 420
27 Payne JT, Andorfer MC, Lewis JC. Angew. Chem. Int. Ed. 2013; 52: 5271
28 Cabrita L, Dai W, Bottomley SP. BMC Biotechnol. 2006; 6: 12
29 Wichmann R, Vasic-Racki D. Adv. Biochem. Engin./Biotechnol. 2005; 92: 225
30 Lang A, Polnick S, Nicke T, William P, Patallo EP, Naismith JH, van Pée K.-H. Angew. Chem. Int. Ed. 2011; 50: 2951
31 Bloom JD, Labthavikul ST, Otey CR, Arnold FH. Proc. Natl. Acad. Sci. U.S.A. 2006; 103: 5869
32 Poor, C. B.; Andorfer, M. C.; Lewis, J. C. Improving the Halogenase Activity and Stability of RebH via Directed Evolution; manuscript submitted for publication.