Expansion of enzymatic Friedel-Crafts alkylation on indoles: Acceptance of unnatural β-unsaturated allyl diphospates by dimethylallyl-tryptophan synthases

Organic Letters

Volumn 14, Issue 18, 2012, Pages 4882-4885

  Liebhold, Mike ^a   Xie, Xiulan ^a   Li, Shu Ming ^a  

^a PHILIPPS UNIVERSITY MARBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

DIMETHYLALLYLTRANSFERASE; INDOLE DERIVATIVE; TRANSFERASE; TRYPTOPHAN; TRYPTOPHAN DIMETHYLALLYLTRANSFERASE;

ALKYLATION; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; METABOLISM; NUCLEAR MAGNETIC RESONANCE;

ALKYL AND ARYL TRANSFERASES; ALKYLATION; CATALYSIS; DIMETHYLALLYLTRANSTRANSFERASE; INDOLES; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; TRYPTOPHAN;

EID: 84868218912     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol302207r     Document Type: Article

References (16)

1. (a) Heide, L. Curr. Opin. Chem. Biol. 2009, 13, 171-179.
2. (b) Yazaki, K.; Tsurumaru, Y. Phytochemistry 2009, 70, 1739-1745.
3. (c) Li, S.-M. Nat. Prod. Rep. 2010, 27, 57-78.
4. (a) Yu, X.; Liu, Y.; Xie, X.; Zheng, X.-D.; Li, S.-M. J. Biol. Chem. 2012, 287, 1371-1380.
5. (b) Yu, X.; Xie, X.; Li, S.-M. Appl. Microbiol. Biotechnol. 2011, 92, 737-748.
6. (c) Yu, X.; Li, S.-M. ChemBioChem2011, 12, 2280-2283.
7. (d) Ozaki, T.; Mishima, S.; Nishiyama, M.; Kuzuyama, T. J. Antibiot. 2009, 62, 385-92.
8. Tsai, H. F.; Wang, H.; Gebler, J. C.; Poulter, C. D.; Schardl, C. L. Biochem. Biophys. Res. Commun. 1995, 216, 119-125.
9. (a) Sanchez, J. F.; Entwistle, R.; Hung, J. H.; Yaegashi, J.; Jain, S.; Chiang, Y. M.; Wang, C. C.; Oakley, B. R. J. Am. Chem. Soc. 2011, 133, 4010-7.
10. (b) Chooi, Y. H.; Wang, P.; Fang, J.; Li, Y.; Wu, K.; Wang, P.; Tang, Y. J. Am. Chem. Soc. 2012, 134, 9428-37.
11. Woodside, A. B.; Huang, Z.; Poulter, C. D. Org. Synth. 1988, 66, 211-215.
12. (a) Kremer, A.; Westrich, L.; Li, S.-M. Microbiology 2007, 153, 3409-3416.
13. (b) Unsöld, I. A.; Li, S.-M. Microbiology 2005, 151, 1499-1505.
14. Takahashi, S.; Takagi, H.; Toyoda, A.; Uramoto, M.; Nogawa, T.; Ueki, M.; Sakaki, Y.; Osada, H. J. Bacteriol. 2010, 192, 2839-2851.
15. (a) Metzger, U.; Schall, C.; Zocher, G.; Unsöld, I.; Stec, E.; Li, S.-M.; Heide, L.; Stehle, T. Proc. Natl. Acad. Sci. U.S.A 2009, 106, 14309-14314.
16. (b) Lik, L. Y. P.; Tanner, M. E. J. Am. Chem. Soc. 2009, 131, 13932-13933.