Opportunities for merging chemical and biological synthesis

Current Opinion in Biotechnology

Volumn 30, Issue , 2014, Pages 1-8

  Wallace, Stephen ^a   Balskus, Emily P ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BIOCOMPATIBILITY; BIOSYNTHESIS; MANUFACTURE; METABOLISM; MOLECULES;

BIOLOGICAL CATALYSTS; CHEMICAL AND BIOLOGICALS; CHEMICAL MANUFACTURES; CHEMICAL PRODUCTION; COMMODITY CHEMICALS; DESIGN PRINCIPLES; MICROBIAL METABOLISM; ORTHOGONAL TECHNOLOGIES;

ORGANIC CHEMICALS;

BIOCATALYSIS; BIOCHEMISTRY; BIOCOMPATIBILITY; BIOENGINEERING; BIOSYNTHESIS; BIOTECHNOLOGY; CATALYST; CELL METABOLISM; CHEMICAL BOND; CHEMICAL INTERACTION; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; ENZYME ACTIVITY; ENZYME MECHANISM; IN VITRO STUDY; IN VIVO STUDY; MEDICAL RESEARCH; MICROBIAL METABOLISM; MOLECULAR BIOLOGY; MOLECULAR SIZE; NONHUMAN; ORGANIC CHEMISTRY; PRIORITY JOURNAL; REVIEW; CATALYSIS; METABOLIC ENGINEERING; PROCEDURES; PROTEIN ENGINEERING; SYNTHESIS;

CATALYSIS; CHEMISTRY TECHNIQUES, SYNTHETIC; CHEMISTRY, ORGANIC; METABOLIC ENGINEERING; PROTEIN ENGINEERING;

EID: 84898915058     PISSN: 09581669     EISSN: 18790429     Source Type: Journal    
DOI: 10.1016/j.copbio.2014.03.006     Document Type: Review

References (55)

1. Nicolaou K.C. The emergence of the structure of the molecule and the art of its synthesis. Angew Chem Int Ed 2013, 52:131-146.
2. Nicolaou K.C., Hale C.R.H., Nilewski C., Ioannidou H.A. Constructing molecular complexity and diversity: total synthesis of natural products of biological and medicinal importance. Chem Soc Rev 2012, 41:5185-5238.
3. Schreiber S. Organic synthesis toward small-molecule probes and drugs. Proc Natl Acad Sci U S A 2011, 108:6699-6702.
4. Keasling J. Manufacturing molecules through metabolic engineering. Science 2010, 330:1355-1358.
5. Carothers J.M., Goler J.A., Keasling J.D. Chemical synthesis using synthetic biology. Curr Opin Biotechnol 2009, 20:498-503.
6. Chen Y., Nielsen J. Advances in metabolic pathway and strain engineering paving the way for sustainable production of chemical building blocks. Curr Opin Biotechnol 2013, 24:965-972.
7. Rabinovitch-Deere C.A., Oliver J.W.K., Rodriguez G.M., Atsumi S. Synthetic biology and metabolic engineering approaches to produce biofuels. Chem Rev 2013, 113:4611-4632.
8. Na D., Park J.H., Jang Y.-S., Lee J.W., Lee S.Y. Systems metabolic engineering of Escherichia coli for chemicals, materials, biofuels, and pharmaceuticals. Systems Metabolic Engineering 2012, 117-149. Springer, Netherlands. C. Wittmann, S.Y. Lee (Eds.).
9. Wang M., Si T., Zhao H. Biocatalyst development by directed evolution. Bioresour Technol 2012, 115:117-125.
10. Bornscheuer U.T., Huisman G.W., Kazlauskas R.J., Lutz S., Moore J.C., Robins K. Engineering the third wave of biocatalysis. Nature 2012, 485:185-194.
11. Khersonsky O., Roodvelt C., Tawfik D.S. Enzyme promiscuity: evolutionary and mechanistic aspects. Curr Opin Chem Biol 2006, 10:498-508.
12. Malpartida F., Hopwood D.A. Molecular cloning of the whole biosynthetic pathway of a Streptomyces antibiotic and its expression in a heterologous host. Nature 1984, 309:462-464.
13. Prather K.L.J., Martin C.H. De novo biosynthetic pathways: rational design of microbial chemical factories. Curr Opin Biotechnol 2008, 19:468-474.
14. Paddon C.J., Westfall P.J., Pitera D.J., Benjamin K., Fisher K., McPhee D., Leavell M.D., Tai A., Main A., Eng D., et al. High-level semi-synthetic production of the potent antimalarial artemisinin. Nature 2013, 496:528-532.
15. Conforth J.W. Chem. Br. 1975, 11:342. (Talking Point).
16. Keasling J.D., Mendoza A., Baran P.S. Synthesis: a constructive debate. Nature 2012, 492:188-189.
17. Hafner E.W., Wellner D. Demonstration of imino acids as products of the reactions catalyzed by d- and l-amino acid oxidases. Proc Natl Acad Sci U S A 1971, 68:987-991.
18. Allen J.V., Williams J.M.J. Dynamic kinetic resolution with enzyme and palladium combinations. Tetrahedron Lett 1996, 37:1859-1862.
19. Kim M.-J., Ahn Y., Park J. Dynamic kinetic resolutions and asymmetric transformations by enzymes coupled with metal catalysis. Curr Opin Biotechnol 2002, 13:578-587.
20. Martin-Matute B., Backvall J.E. Dynamic kinetic resolution catalyzed by enzymes and metals. Curr Opin Chem Biol 2007, 11:226-232.
21. Denard C.A., Huang H., Bartlett M.J., Lu L., Tan Y., Zhao H., Hartwig J.F. Cooperative tandem catalysis by an organometallic complex and a metalloenzyme. Angew Chem Int Ed 2013, 52:465-469.
22. 2+ and enzymes - analysis and potential remedies. J Mol Catal B Enzym 2010, 63:149-156.
23. Brooks R.R., Watterson J.R. Nobel Metals and Biological Systems 1992, vol 180. CRC Press, Boca Ranton, FL, USA.
24. Wang Z.J., Clary K.N., Bergman R.G., Raymond K.N., Toste F.D. A supramolecular approach to combining enzymatic and transition metal catalysis. Nat Chem 2013, 5:100-103.
25. Breslow R., Overman L.E. An "artificial enzyme" combining a metal catalytic group and a hydrophobic binding cavity. J Am Chem Soc 1970, 92:1075-1077.
26. Yoshizawa M., Klosterman J.K., Fujita M. Functional molecular flasks: new properties and reactions within discrete, self-assembled hosts. Angew Chem Int Ed 2009, 48:3418-3438.
27. Wiester M.J., Ulmann P.A., Mirkin C.A. Enzyme mimics based upon supramolecular coordination chemistry. Angew Chem Int Ed 2010, 50:114-137.
28. Bhabak K.P., Bhuyan B.J., Mugesh G. Bioinorganic and medicinal chemistry: aspects of gold(I)-protein complexes. Dalton Trans 2011, 10:2099-2111.
29. Kohler V., Wilson Y.M., Durrenberger M., Ghislieri D., Churakova E., Quinto T., Knorr L., Haussinger D., Hollmann F., Turner N.J., Ward T.R. Synthetic cascades are enabled by combining biocatalysts with artificial metalloenzymes. Nat Chem 2013, 5:93-99.
30. Khersonsky O., Tawfik D.S. Enzyme promiscuity: a mechanistic and evolutionary perspective. Ann Rev Biochem 2010, 79:471-505.
31. Gatti-Lafranconi P., Hollfelder F. Flexibility and reactivity in promiscuous enzymes. ChemBioChem 2013, 14:285-292.
32. Wilson M.E., Whitesides G.M. Conversion of a protein to a homogeneous asymmetric hydrogenation catalyst by site specific modification with a diphosphinerhodium(I) moiety. J Am Chem Soc 1978, 100:306-307.
33. Ward T.R. Artificial metalloenzymes based on the biotin-streptavidin technology: enantioselective catalysis and beyond. Acc Chem Res 2011, 44:47-57.
34. Lewis J.C. Artificial metalloenzymes and metallopeptide catalysts for organic synthesis. ACS Catal 2013, 3:2954-2975.
35. Hyster T.K., Knorr L., Ward T.R., Rovis T. Biotinylated Rh(III) complexes in engineered streptavidin for accelerated asymmetric CH activation. Science 2012, 338:500-503.
36. Zimbron J.M., Heinisch T., Schmid M., Hamels D., Nogueira E.S., Schirmer T., Ward T.R. A duel anchoring strategy for the localization and activation of artificial metalloenzymes based on the biotin-streptavidin technology. J Am Chem Soc 2013, 135:5384-5388.
37. Schwizer F., Kohler V., Durrenberger M., Knorr L., Ward T.R. Genetic optimization of the catalytic efficiency of artificial imine reductases based on the biotin-streptavidin technology. ACS Catal 2013, 3:1752-1755.
38. Monnard F.W., Nogueira E.S., Heinisch T., Schirmer T., Ward T.R. Human carbonic anhydrase II as host protein for the creation of artificial metalloenzymes: the asymmetric transfer hydrogenation of imines. Chem Sci 2013, 4:3269-3274.
39. Coelho P.S., Brustard E.M., Kannan A., Arnold F.H. Olefin cyclopropanation via carbene transfer catalyzed by engineered cytochrome P450 enzymes. Science 2013, 339:307-309.
40. Coelho P.S., Wang Z.J., Ener M.E., Baril S.A., Kannan A., Arnold F.H., Brustard E.M. A serine-substituted P450 catalyzes highly efficient carbene transfer to olefins in vivo. Nat Chem Biol 2013, 9:485-487.
41. McIntosh J.A., Coelho P.S., Farwell C.C., Wang Z.J., Lewis J.C., Brown T.R., Arnold F.H. Enantioselective intramolecular CH amination catalyzed by engineered cytochrome P450 enzymes in vitro and in vivo. Angew Chem Int Ed 2013, 52:9309-9312.
42. Wang Z.J., Peck N.E., Renata H., Arnold F.H. Cytochrome P450-catalysed insertion of carbenoids into NH bonds. Chem Sci 2014, 5:598-601.
43. Matthews M.L., Chang W., Layne A.P., Miles L.A., Krebs C., Bollinger J.M. Direct nitration and azidation of aliphatic carbons by an iron-dependent halogenase. Nat Chem Biol 2014, 10:209-215.
44. Neuberg C., Hirsch J. Uber den Verlauf der alkoholischen-Garung bei alkalischer Reaktion. II. Garung mit lebender Hefe in alkalischen Losungen. Biochem Z 1919, 96:175-202.
45. Neuberg C., Hirsch J. Die dritte Vergarungform des Zurkers. Biochem Z 1919, 100:304-322.
46. 3Na. Greene's Protective Groups in Organic Synthesis 2006, John Wiley & Sons, Inc., Hoboken, New Jersey, USA. 4th ed.
47. Kaspar H.F., Holland A.J., Mountfort D.O. Simultaneous butyrate oxidation by Syntrophomonas wolfei and catalytic olefin reduction in absence of interspecies hydrogen transfer. Arch Microbiol 1987, 147:334-339.
48. Vigh L., Los D.A., Horvath I., Murata N. The primary signal in the biological perception of temperature: Pd-catalyzed hydrogenation of membrane lipids stimulated the expression of the desA gene in Synechocystis PCC6803. Proc Natl Acad Sci U S A 1993, 90:9090-9094.
49. Robbins D.W., Hartwig J.F. A simple, multidimensional approach to high-throughput discovery of catalytic reactions. Science 2011, 333:1423-1427.
50. McNally A., Prier C.K., MacMillan D.W. Discovery of an α-amino CH arylation reaction using the strategy of accelerated serendipity. Science 2011, 334:1114-1117.
51. Lang K., Chin J.W. Bioorthogonal reactions for labeling proteins. ACS Chem Biol 2014, 9:16-20.
52. Sletten E.M., Bertozzi C.R. Bioorthogonal chemistry: fishing for selectivity in a sea of functionality. Angew Chem Int Ed 2009, 48:6974-6998.
53. Patterson D.M., Nazarova L.A., Prescher J.A. Finding the right (bioorthogonal) chemistry. ACS Chem Biol 2014, 9:592-605.
54. Bertozzi C.R. A decade of bioorthogonal chemistry. Acc Chem Res 2011, 44:651-653.
55. Lee Y., Umeano A., Balskus E.P. Rescuing auxotrophic microorganisms with nonenzymatic chemistry. Angew Chem Int Ed 2013, 52:11800-11803.