The thioesterase domain from the pimaricin and erythromycin biosynthetic pathways can catalyze hydrolysis of simple thioester substrates

Bioorganic and Medicinal Chemistry Letters

Volumn 17, Issue 11, 2007, Pages 3034-3037

  Sharma, Krishna K ^a   Boddy, Christopher N ^a  

^a SYRACUSE UNIVERSITY   (United States)

Author keywords

Acyl enzyme intermediate; Antibiotics; Biosynthesis; Hydrolysis; Polyketides; Thioesterase

Indexed keywords

ERYTHROMYCIN; ERYTHRONOLIDE DERIVATIVE; NATAMYCIN; THIOL ESTER HYDROLASE;

ARTICLE; CATALYSIS; DRUG HYDROLYSIS; DRUG ISOLATION; DRUG STRUCTURE; ENZYME SPECIFICITY; PROTEIN DOMAIN; STEREOCHEMISTRY;

BIOSYNTHETIC PATHWAYS; CATALYSIS; CYSTEAMINE; ERYTHROMYCIN; ESTERS; HYDROLYSIS; NATAMYCIN; POLYKETIDE SYNTHASES; PROTEIN STRUCTURE, TERTIARY; RECOMBINANT PROTEINS; SUBSTRATE SPECIFICITY; SULFUR COMPOUNDS; THIOLESTER HYDROLASES;

EID: 34247853435     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2007.03.060     Document Type: Article

References (23)

1. Hill A.M. Nat. Prod. Rep. 23 (2006) 256
2. Floss H.G. J. Biotechnol. 124 (2006) 242
3. Weissman K.J., and Leadlay P.E. Nat. Rev. Microbiol. 3 (2005) 925
4. Cane D.E., Walsh C.T., and Khosla C. Science 282 (1998) 63
5. Aparicio J.F., Fouces R., Olivera N., Mendes M.V., and Martin J.F. Chem. Biol. 7 (2000) 895
6. Kohli R.M., and Walsh C.T. Chem. Commun. (2003) 297
7. Gokhale R.S., Hunziker D., Cane D.E., and Khosla C. Chem. Biol. 6 (1999) 117
8. Lu H., Tsai S.-C., Khosla C., and Cane D.E. Biochemistry 41 (2002) 12590
9. Weissman K.J., Smith C.J., Hanefeld U., Aggarwal R., Bycroft M., Staunton J., and Leadlay P.F. Angew. Chem. Int. Ed 37 (1998) 1437
10. Chan P.C.-M., Chong J.M., and Kousha K. Tetrahedron 50 (1994) 2703
11. Evans D.A., Bartroli J., and Shih T.L. J. Am. Chem. Soc. 103 (1981) 2127
12. Evans D.A., Ng H.P., Clark J.S., and Rieger D.L. Tetrahedron 48 (1992) 2127
13. Gilbert I.H., Ginty M., O'Neill J.A., Simpson T.J., Staunton J., and Willis C.L. Bioorg. Med. Chem. Lett. 15 (1995) 1587
14. Oikawa Y., Sugano K., and Yonemitsu O. J. Org. Chem. 43 (1978) 2087
15. Arthur C., Cox R.J., Crosby J., Rahman M.M., Simpson T.J., Soulas F., Spogli R., Szafranska A.E., Westcott J., and Winfield C.J. Chem. Bio. Chem. (2002) 253
16. The pim TE did not hydrolyze the pimaricin. pim TE (2.0 mM) was treated with pimaricin (2.0 mM) in 50 mM phosphate buffer at pH 8.0. LCMS analysis of the reaction showed no hydrolysis after 24 h at 37 °C.
17. Boddy C.N., Schneider T.L., Hotta K., Walsh C.T., and Khosla C. J. Am. Chem. Soc. 125 (2003) 3428
18. Samel S.A., Bjorn W., Marahiel M.A., and Essen L.-O. J. Mol. Biol. 359 (2006) 876
19. Tseng C.C., Bruner S.D., Kohli R.M., Marahiel M.A., Walsh C.T., and Sieber S.A. Biochemistry 41 (2002) 13350
20. Trauger J.W., Kohli R.M., Mootz H.D., Marahiel M.A., and Walsh C.T. Nature 407 (2000) 215
21. Trauger J.W., Kohli R.M., and Walsh C.T. Biochemistry 40 (2001) 7092
22. Kohli R.M., Walsh C.T., and Burkart M.D. Nature 418 (2002) 658
23. Boddy C.N., Hotta K., Tse M.L., Watts R.E., and Khosla C. J. Am. Chem. Soc. 126 (2004) 7436