Assembly of asperlicin peptidyl alkaloids from anthranilate and tryptophan: A two-enzyme pathway generates heptacyclic scaffold complexity in asperlicin E

Journal of the American Chemical Society

Volumn 134, Issue 42, 2012, Pages 17444-17447

  Haynes, Stuart W ^a   Gao, Xue ^b   Tang, Yi ^b   Walsh, Christopher T ^a  

^a HARVARD MEDICAL SCHOOL   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTHRANILATE; ASPERGILLUS ALLIACEUS; ASSEMBLY LINE; BIOCHEMICAL CHARACTERIZATION; BUILDING BLOCKES; EN-ROUTE; FUNGAL METABOLITES; GENE CLUSTERS; GENETIC CHARACTERIZATION; GENETIC MANIPULATIONS; MONOOXYGENASES; OXIDATIVE CYCLIZATION;

AMINO ACIDS; BIOCHEMISTRY; BIOSYNTHESIS; SCAFFOLDS;

METABOLITES;

ANTHRANILIC ACID; ASPERLICIN; ASPERLICIN E; NONRIBOSOMAL PEPTIDE SYNTHETASE; TRYPTOPHAN; UNCLASSIFIED DRUG; UNSPECIFIC MONOOXYGENASE;

ARTICLE; ASPERGILLUS ALLIACEUS; CYCLIZATION; DRUG SYNTHESIS; ENZYME ACTIVITY; GENE CLUSTER; GENETIC MANIPULATION; NONHUMAN; PROTEIN ASSEMBLY;

ALKALOIDS; BENZODIAZEPINONES; BIOCATALYSIS; MIXED FUNCTION OXYGENASES; MOLECULAR CONFORMATION; ORTHO-AMINOBENZOATES; PEPTIDES; TRYPTOPHAN;

EID: 84867755046     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja308371z     Document Type: Article

References (22)

1. Ames, B. D.; Liu, X.; Walsh, C. T. Biochemistry 2010, 49, 8564
2. Takahashi, C.; Matsushita, T.; Doi, M.; Minoura, K.; Shingu, T.; Kumeda, Y.; Numata, A. J. Chem. Soc., Perkin Trans. 1 1995, 2345
3. Yin, W. B.; Grundmann, A.; Cheng, J.; Li, S. M. J. Biol. Chem. 2009, 284, 100
4. Gao, X.; Chooi, Y. H.; Ames, B. D.; Wang, P.; Walsh, C. T.; Tang, Y. J. Am. Chem. Soc. 2011, 133, 2729
5. Chang, R.; Lotti, V.; Monaghan, R.; Birnbaum, J.; Stapley, E.; Goetz, M.; Albers-Schonberg, G.; Patchett, A.; Liesch, J.; Hensens, O. Science 1985, 230, 177
6. Liesch, J. M.; Hensens, O. D.; Zink, D. L.; Goetz, M. A. J. Antibiot. 1988, 41, 878
7. Ames, B. D.; Haynes, S. W.; Gao, X.; Evans, B. S.; Kelleher, N. L.; Tang, Y.; Walsh, C. T. Biochemistry 2011, 50, 8756
8. Ames, B. D.; Walsh, C. T. Biochemistry 2010, 49, 3351
9. Haynes, S. W.; Ames, B. D.; Gao, X.; Tang, Y.; Walsh, C. T. Biochemistry 2011, 50, 5668
10. Liu, J. F.; Kaselj, M.; Isome, Y.; Chapnick, J.; Zhang, B.; Bi, G.; Yohannes, D.; Yu, L.; Baldino, C. M. J. Org. Chem. 2005, 70, 10488
11. Gao, X.; Haynes, S. W.; Ames, B. D.; Wang, P.; Vien, L. P.; Walsh, C. T.; Tang, Y. Nat. Chem. Biol. 2012, 8, 823
12. Nayak, T.; Szewczyk, E.; Oakley, C. E.; Osmani, A.; Ukil, L.; Murray, S. L.; Hynes, M. J.; Osmani, S. A.; Oakley, B. R. Genetics 2006, 172, 1557
13. Szewczyk, E.; Nayak, T.; Oakley, C. E.; Edgerton, H.; Xiong, Y.; Taheri-Talesh, N.; Osmani, S. A.; Oakley, B. R. Nat. Protoc. 2006, 1, 3111
14. Hochlowski, J. E.; Mullally, M. M.; Spanton, S. G.; Whittern, D. N.; Hill, P.; McAlpine, J. B. J. Antibiot. 1993, 46, 380
15. Karwowski, J. P.; Jackson, M.; Rasmussen, R. R.; Humphrey, P. E.; Poddig, J. B.; Kohl, W. L.; Scherr, M. H.; Kadam, S.; McAlpine, J. B. J. Antibiot. 1993, 46, 374
16. Sun, H. H.; Barrow, C. J.; Sedlock, D. M.; Gillum, A. M.; Cooper, R. J. Antibiot. 1994, 47, 515
17. Sun, H. H.; Barrow, C. J.; Cooper, R. J. Nat. Prod. 1995, 58, 1575
18. Rahbaek, L.; Breinholt, J.; Frisvad, J. C.; Christophersen, C. J. Org. Chem. 1999, 64, 1689
19. Rahbaek, L.; Breinholt, J. J. Nat. Prod. 1999, 62, 904
20. Ookura, R.; Kito, K.; Ooi, T.; Namikoshi, M.; Kusumi, T. J. Org. Chem. 2008, 73, 4245
21. Zhang, D.; Yang, X.; Kang, J. S.; Choi, H. D.; Son, B. W. J. Antibiot. 2008, 61, 40
22. Joshi, B. K.; Gloer, J. B.; Wicklow, D. T.; Dowd, P. F. J. Nat. Prod. 1999, 62, 650