Unprecedented acetoacetyl-coenzyme A synthesizing enzyme of the thiolase superfamily involved in the mevalonate pathway

Proceedings of the National Academy of Sciences of the United States of America

Volumn 107, Issue 25, 2010, Pages 11265-11270

  Okamura, Eiji ^a   Tomita, Takeo ^a   Sawa, Ryuichi ^b   Nishiyama, Makoto ^a   Kuzuyama, Tomohisa ^a  

^a UNIVERSITY OF TOKYO   (Japan)

^b INSTITUTE OF MICROBIAL CHEMISTRY   (Japan)

Author keywords

Acetoacetyl CoA; Streptomyces; Terpenoid

Indexed keywords

ACETYL COENZYME A ACETYLTRANSFERASE; COENZYME A; MALONYL COENZYME A; MEVALONIC ACID; NPHT7 ENZYME; UNCLASSIFIED DRUG; ACETOACETYL COA SYNTHASE, STREPTOMYCES; ACETOACETYL COENZYME A; ACETOACETYL-COA SYNTHASE, STREPTOMYCES; ACYL COENZYME A; BACTERIAL PROTEIN; HYDROXYBUTYRIC ACID; HYDROXYMETHYLGLUTARYL COENZYME A SYNTHASE; LONG CHAIN FATTY ACID COENZYME A LIGASE; POLY(3 HYDROXYBUTYRIC ACID); POLY-BETA-HYDROXYBUTYRATE; POLYESTER; RECOMBINANT PROTEIN; TERPENE;

ARTICLE; BACTERIAL STRAIN; CARBOXY TERMINAL SEQUENCE; ENZYME ACTIVITY; ENZYME PURIFICATION; ENZYME SYNTHESIS; ESCHERICHIA COLI; IN VIVO STUDY; PRIORITY JOURNAL; PROTEIN EXPRESSION; STREPTOMYCES; AMINO ACID SEQUENCE; CHEMISTRY; ENZYMOLOGY; GENE EXPRESSION REGULATION; GENETICS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; KINETICS; METABOLISM; MOLECULAR GENETICS; MULTIGENE FAMILY; PHYSIOLOGY; SEQUENCE HOMOLOGY;

ESCHERICHIA COLI; STREPTOMYCES; STREPTOMYCES SP.;

ACYL COENZYME A; AMINO ACID SEQUENCE; BACTERIAL PROTEINS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; COENZYME A LIGASES; ESCHERICHIA COLI; GENE EXPRESSION REGULATION, BACTERIAL; HYDROXYBUTYRATES; HYDROXYMETHYLGLUTARYL-COA SYNTHASE; KINETICS; MEVALONIC ACID; MOLECULAR SEQUENCE DATA; MULTIGENE FAMILY; POLYESTERS; RECOMBINANT PROTEINS; SEQUENCE HOMOLOGY, AMINO ACID; STREPTOMYCES; TERPENES;

EID: 77954919291     PISSN: 00278424     EISSN: 10916490     Source Type: Journal    
DOI: 10.1073/pnas.1000532107     Document Type: Article

References (31)

1. Haapalainen AM, Merilainen G, Wierenga RK (2006) The thiolase superfamily: condensing enzymes with diverse reaction specificities. Trends Biochem Sci 31:64-71.
2. Heath RJ, Rock CO (2002) The Claisen condensation in biology. Nat Prod Rep 19:581-596.
3. Austin MB, Noel JP (2003) The chalcone synthase superfamily of type III polyketide synthases. Nat Prod Rep 20:79-110.
4. Jiang C, Kim SY, Suh DY (2008) Divergent evolution of the thiolase superfamily and chalcone synthase family. Mol Phylogenet Evol 49:691-701.
5. Davies C, Heath RJ, White SW, Rock CO (2000) The 1.8 A crystal structure and active-site architecture of beta-ketoacyl-acyl carrier protein synthase III (FabH) from Escherichia coli. Structure 8:185-195.
6. Qiu X, et al. (2001) Refined structures of beta-ketoacyl-acyl carrier protein synthase III. J Mol Biol 307:341-356.
7. Musayev F, Sachdeva S, Scarsdale JN, Reynolds KA, Wright HT (2005) Crystal structure of a substrate complex of Mycobacterium tuberculosis beta-ketoacyl-acyl carrier protein synthase III (FabH) with lauroyl-coenzyme A. J Mol Biol 346:1313-1321.
8. Qiu X, et al. (2005) Crystal structure and substrate specificity of the beta-ketoacyl-acyl carrier protein synthase III (FabH) from Staphylococcus aureus. Protein Sci 14:2087-2094.
9. White SW, Zheng J, Zhang YM , Rock CO (2005) The structural biology of type II fatty acid biosynthesis. Annu Rev Biochem 74:791-831.
10. Takahashi S, Kuzuyama T, Seto H (1999) Purification, characterization, and cloning of a eubacterial 3-hydroxy-3-methylglutaryl coenzyme A reductase, a key enzyme involved in biosynthesis of terpenoids. J Bacteriol 181:1256-1263.
11. Takagi M, Kuzuyama T, Takahashi S, Seto H (2000) A gene cluster for the mevalonate pathway from Streptomyces sp. Strain CL 190. J Bacteriol 182:4153-4157.
12. Kaneda K, Kuzuyama T, Takagi M, Hayakawa Y, Seto H (2001) An unusual isopentenyl diphosphate isomerase found in the mevalonate pathway gene cluster from Streptomyces sp strain CL190. Proc Natl Acad Sci USA 98:932-937.
13. Kawasaki T, et al. (2003) A relationship between the mevalonate pathway and isoprenoid production in actinomycetes. J Antibiot (Tokyo) 56:957-966.
14. Kawasaki T, et al. (2006) Biosynthesis of a natural polyketide-isoprenoid hybrid compound, furaquinocin A: identification and heterologous expression of the gene cluster. J Bacteriol 188:1236-1244.
15. Saleh O, Gust B, Boll B, Fiedler HP, Heide L (2009) Aromatic prenylation in phenazine biosynthesis: dihydrophenazine-1-carboxylate dimethylallyltransferase from Streptomyces anulatus. J Biol Chem 284:14439-14447.
16. Zhang YM, et al. (2001) Identification and analysis of the acyl carrier protein (ACP) docking site on beta-ketoacyl-ACP synthase III. J Biol Chem 276:8231-8238.
17. Heath RJ, Rock CO (1996) Inhibition of beta-ketoacyl-acyl carrier protein synthase III (FabH) by acyl-acyl carrier protein in Escherichia coli. J Biol Chem 271:10996-11000.
18. Kuzuyama T, Dairi T, Yamashita H, Shoji Y, Seto H (2004) Heterologous mevalonate production in Streptomyces lividans TK23. Biosci Biotechnol Biochem 68:931-934.
19. Dairi T, Aisaka K, Katsumata R, Hasegawa M (1995) A self-defense gene homologous to tetracycline effluxing gene essential for antibiotic production in Streptomyces aureofaciens. Biosci Biotechnol Biochem 59:1835-1841.
20. Kieser T, Bibb MJ, Buttner MJ, Chater KF, Hopwood DA (2000) Practice Streptomyces Genetics (John Innes Foundation, Norwich, United Kingdom).
21. Kim SY, et al. (2009) Cloning and heterologous expression of the cyclooctatin biosynthetic gene cluster afford a diterpene cyclase and two p450 hydroxylases. Chem Biol 16:736-743.
22. Eckermann S, et al. (1998) New pathway to polyketides in plants. Nature 396:387-390.
23. Funa N, et al. (1999) A new pathway for polyketide synthesis in microorganisms. Nature 400:897-899.
24. Rodriguez-Villalon A, Perez-Gil J, Rodriguez-ConcepcionM(2008) Carotenoid accumulation in bacteria with enhanced supply of isoprenoid precursors by upregulation of exogenous or endogenous pathways. J Biotechnol 135:78-84.
25. Harada H, et al. (2009) Efficient synthesis of functional isoprenoids from acetoacetate through metabolic pathway-engineered Escherichia coli. Appl Microbiol Biotechnol 81:915-925.
26. Yoon SH, et al. (2006) Enhanced lycopene production in Escherichia coli engineered to synthesize isopentenyl diphosphate and dimethylallyl diphosphate from mevalonate. Biotechnol Bioeng 94:1025-1032.
27. Keasling JD (2008) Synthetic biology for synthetic chemistry. ACS Chem Biol 3:64-76.
28. Jez JM, Ferrer JL, Bowman ME, Dixon RA, Noel JP (2000) Dissection of malonyl-coenzyme A decarboxylation from polyketide formation in the reaction mechanism of a plant polyketide synthase. Biochemistry 39:890-902.
29. Han L, Lobo S, Reynolds KA (1998) Characterization of beta-ketoacyl-acyl carrier protein synthase III from Streptomyces glaucescens and its role in initiation of fatty acid biosynthesis. J Bacteriol 180:4481-4486.
30. Hayashi O, Satoh K (2006) Determination of acetyl-CoA and malonyl-CoA in germinating rice seeds using the LC-MS/MS technique. Biosci Biotechnol Biochem 70:2676-2681.
31. Middleton B (1974) The kinetic mechanism and properties of the cytoplasmic acetoacetyl-coenzyme A thiolase from rat liver. Biochem J 139:109-121.