A labeled substrate approach to discovery of biocatalytic reactions: A proof of concept transformation with N-methylindole

Journal of the American Chemical Society

Volumn 134, Issue 30, 2012, Pages 12378-12381

  Rogers, Jamie L ^a   MacMillan, John B ^a  

^a UNIVERSITY OF TEXAS SOUTHWESTERN MEDICAL CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BACTERIAL CELLS; BIOCATALYSIS; BIOCATALYTIC REACTION; INDOLE OXIDATION; LABELED SUBSTRATES; MARINE BACTERIUM; ORGANIC SUBSTRATE; ORGANIC TRANSFORMATIONS; PHARMACEUTICAL INDUSTRY; PRIMARY SCREENING; PROOF OF CONCEPT; SMALL MOLECULES;

CELL CULTURE;

SUBSTRATES;

CARBON 13; INDOLE DERIVATIVE; OXINDOLE;

ARTICLE; BACTERIAL CELL; BIOCATALYSIS; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; NONHUMAN; OXIDATION; SCREENING;

ACTINOBACTERIA; BIOCATALYSIS; BIOTRANSFORMATION; CARBON ISOTOPES; INDOLES; OXIDATION-REDUCTION; OXYGEN;

EID: 84864424508     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja304767m     Document Type: Article

References (33)

1. Schmid, A.; Dordick, J. S.; Hauer, B.; Kiener, A.; Wubbolts, M.; Witholt, B. Nature 2001, 409, 258
2. Straathof, A. J.; Panke, S.; Schmid, A. Curr. Opin. Biotechnol. 2002, 13, 548
3. Tao, J.; Xu, J. H. Curr. Opin. Chem. Biol. 2009, 13, 43
4. Pollard, D. J.; Woodley, J. M. Trends Biotechnol. 2006, 25, 66
5. Buckland, B. C.; Drew, S. C.; Connors, N. C.; Chartrain, M. M.; Lee, C.; Salmon, P. M.; Gbewonyo, K.; Zhou, W.; Gailliot, P.; Singhvi, R.; Olewinski, R. C.; Sun, W. J.; Reddy, J.; Zhang, J.; Jackey, B. A.; Taylor, C.; Goklen, K. E.; Junker, B.; Greasham, R. L. Metab. Eng. 1999, 1, 63
6. Martinez, C. A.; Hu, S.; Dumond, Y.; Tao, J.; Kelleher, P.; Tully, L. Org. Process Res. Dev. 2008, 12, 392
7. Glaser, V. Gene Eng. Biotechnol. News 2008, 28, 30
8. Hu, Y.; Legako, A. G.; Espindola, A.-P. D. M.; MacMillan, J. B. J. Org. Chem. 2012, 77, 3401
9. Pan, E.; Jamison, M.; Yousufuddin, M.; MacMillan, J. B. Org. Lett. 2012, 14, 2390
10. Hu, Y.; MacMillan, J. B. Org. Lett. 2011, 13, 6580
11. Hu, Y.; Espindola, A.-P. D. M.; Steward, N. A.; Wei, S.; Posner, B. A.; MacMillan, J. B. Bioorg. Med. Chem. 2011, 19, 5183
12. Alphand, V.; Furstoss, R. J. Mol. Catal. B: Enzym. 2000, 9, 209
13. Kanan, M. W.; Rozenman, M. M.; Sakurai, K.; Syder, T. M.; Liu, D. R. Nature 2004, 431, 545
14. McNally, A.; Prier, C. K.; MacMillan, D. W. C. Science 2011, 334, 1114
15. Robbins, D. W.; Hartwig, J. H. Science 2011, 333, 1423
16. Medici, R.; Garaycoechea, J. I.; Dettorre, L. A.; Iribarren, A. M.; Lewkowicz, E. S. Biotechnol. Lett. 2011, 33, 1999
17. Trost, B. M.; Kie, J.; Sieber, J. D. J. Am. Chem. Soc. 2011, 133, 20611
18. Ling, K.; Li, W.; Sayre, L. M. J. Am. Chem. Soc. 2008, 130, 933
19. Jimenez, J. L.; Huber, U.; Moore, R. E.; Patterson, G. M. L. J. Nat. Prod. 1999, 62, 569
20. Birch, A. L.; Wright, I. I. J. Chem. Soc., Chem Commun. 1969, 12, 644
21. Liu, J. R.; Jiang, Z. Y.; Wang, R. R.; Zheng, Y. T.; Chen, J. L.; Zhang, X. M.; Ma, Y. B. Org. Lett. 2007, 9, 4127
22. Onyeibor, O.; Croft, S. L.; Dodson, H. I.; Feiz-Haddad, M.; Kendrick, H.; Millington, N. J.; Parapini, S.; Phillips, R. M.; Seville, S.; Shnyder, S. D. J. Med. Chem. 2005, 48, 2701
23. Gaywood, A. P.; McNab, H. Synthesis 2010, 8, 1361
24. Azadi-Ardakani, M.; Alkhader, M. A.; Lipplatt, J. H.; Patel, D. I.; Smalley, R. R.; Higson, S. J. Chem. Soc., Perkin Trans. 1 1986, 6, 1107
25. Kiraz, C. I. A.; Enge, T. J.; Jimenez, L. S. J. Org. Chem. 2004, 69, 2200
26. Ganachaud, C.; Garfagnoli, V.; Tron, T.; Lacazio, G. Tetrahedron Lett. 2008, 49, 2476
27. Ensley, B. D.; Ratzkin, B. J.; Osslund, T. D.; Simon, M. J.; Wackett, L. P.; Gibson, D. T. Science 1983, 222, 167
28. Murdock, D.; Ensley, B. D.; Serdar, C.; Thalen, M. Bio/Technology 1993, 11, 381
29. Mermod, N.; Harayama, S.; Tinnis, K. N. Bio/Technology 1986, 4, 321
30. Meyer, A.; Wursten, M.; Schmidt, A.; Kohler, H-P. E.; Witholt, B. J. Biol. Chem. 2002, 277, 34161
31. Wiktop, B.; Patrick, J. B. J. Am. Chem. Soc. 1951, 73, 2188
32. Ferreira-Torres, C.; Michelleti, M.; Lye, G. J. Biosyst. Eng. 2005, 28, 83
33. Minas, W.; Bailey, J. E.; Duetz, W. Antonie Leeuwenhoek 2000, 78, 297