A dedicated thioesterase of the Hotdog-fold family is required for the biosynthesis of the naphthoquinone ring of vitamin K 1

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

Volumn 106, Issue 14, 2009, Pages 5599-5603

  Widhalm, Joshua R ^a   Oostende, Chloëvan ^a   Furt, Fabienne ^a   Basset, Gilles J C ^a  

^a UNIVERSITY OF NEBRASKA LINCOLN   (United States)

Author keywords

Cyanobacteria; Isoprenoids; Photosynthesis; Phylloquinone

Indexed keywords

1,4 DIHYDROXY 2 NAPHTHOATE; 4 HYDROXYBENZOYL COENZYME A; COENZYME A; GENTISYL COENZYME A; NAPHTHOQUINONE; PHYTOMENADIONE; THIOL ESTER HYDROLASE; UNCLASSIFIED DRUG;

ARTICLE; BACTERIAL GENE; BIOSYNTHESIS; CHEMICAL STRUCTURE; CONTROLLED STUDY; CYANOBACTERIUM; ENZYME ACTIVITY; GENE EXPRESSION; GENE FUNCTION; GENE IDENTIFICATION; GENOMICS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; NONHUMAN; PHOTOSENSITIVITY; PRIORITY JOURNAL; PROTEIN DEGRADATION; SEQUENCE HOMOLOGY; SLR0204 GENE; SYNECHOCYSTIS;

CYANOBACTERIA; HYDROLYSIS; METABOLIC NETWORKS AND PATHWAYS; MUTATION; NAPHTHOLS; NAPHTHOQUINONES; SUBSTRATE SPECIFICITY; THIOLESTER HYDROLASES; VITAMIN K 1;

CYANOBACTERIA; SYNECHOCYSTIS;

EID: 65249118266     PISSN: 00278424     EISSN: 10916490     Source Type: Journal    
DOI: 10.1073/pnas.0900738106     Document Type: Article

References (30)

1. Sakuragi Y, Bryant DA (2006) in Photosystem I: The Light-Driven Plastocyanin:Ferredoxin Oxidoreductase. Advances in Photosynthesis and Respiration, ed Golbeck JH (Springer, Dordrecht), pp 205-222.
2. Collins MD, Jones D (1981) Distribution of isoprenoid quinone structural types in bacteria and their taxonomic implications. Microbiol Rev 45:316-354.
3. - double quinone mutant. Biochim Biophys Acta 461:84-100.
4. Fromme P, Grotjohann I (2006) in Photosystem I: The Light-Driven Plastocyanin:Ferredoxin Oxidoreductase. Advances in Photosynthesis and Respiration, ed Golbeck JH (Springer, Dordrecht), pp 47-69.
5. Vermeer C, et al. (2004) Beyond deficiency: Potential benefits of increased intakes of vitamin K for bone and vascular health. Eur J Nutr 43:325-335.
6. Ichikawa T, Horie-Inoue K, Ikeda K, Blumberg B, Inoue S (2006) Steroid and xenobiotic receptor SXR mediates vitamin K2-activated transcription of extracellular matrixrelated genes and collagen accumulation in osteoblastic cells. J Biol Chem 281:16927-16934.
7. HiratsukaT, etal. (2008) An alternative menaquinone biosynthetic pathway operating in microorganisms. Science 321:1670-1673.
8. 2) and ubiquinone (coenzyme Q): A perspective on enzymatic mechanisms. Vitam Horm 61:173-218.
9. Johnson TW, et al. (2000) Recruitment of a foreign quinone into the A(1) site of photosystem I. I. Genetic and physiological characterization of phylloquinone biosynthetic pathway mutants in Synechocystis sp. pcc 6803. J Biol Chem 275:8523-8530.
10. Wade Johnson T, et al. (2003) The menD and menE homologues code for 2-succinyl- 6-hydroxyl-2,4-cyclohexadiene-1-carboxylate synthase and O-succinylbenzoic acid- CoA ligase in the phylloquinone biosynthetic pathway of Synechocystis sp. PCC 6803. Biochim Biophys Acta 1557:67-76.
11. Sakuragi Y, etal. (2002) Insertional inactivation of the menG gene, encoding 2-phytyl- 1,4-naphthoquinone methyltransferase of Synechocystis sp. PCC 6803, results in the incorporation of 2-phytyl-1,4-naphthoquinone into the A(1) site and alteration of the equilibrium constant between A(1) and F(X) in photosystem I. Biochemistry 41:394-405.
12. Shimada H, et al. (2005) Inactivation and deficiency of core proteins of photosystems I and II caused by genetical phylloquinone and plastoquinone deficiency but retained lamellar structure in a T-DNA mutant of Arabidopsis. Plant J 41:627-637.
13. Gross J, etal. (2006) A plant locus essential for phylloquinone (vitamin K1) biosynthesis originated from a fusion of four eubacterial genes. J Biol Chem 281:17189-17196.
14. 1) methylation affects prenyl quinone distribution, photosystem I abundance, and anthocyanin accumulation in the Arabidopsis AtmenG mutant. J Biol Chem 281:40461-40472.
15. Kim HU, van Oostende C, Basset GJ, Browse J (2008) The AAE14 gene encodes the Arabidopsis o-succinylbenzoyl-CoA ligase that is essential for phylloquinone synthesis and photosystem I function. Plant J 54:272-283.
16. Lefebvre-Legendre L, et al. (2007) Loss of phylloquinone in Chlamydomonas affects plastoquinone pool size and photosystem II synthesis. J Biol Chem 282:13250-13263.
17. 2) biosynthesis: Nucleotide sequence and expression of the menB gene from Escherichia coli. J Bacteriol 174:5057-5062.
18. Truglio JJ, et al. (2003) Crystal structure of Mycobacterium tuberculosis MenB, a key enzyme in vitamin K2 biosynthesis. J Biol Chem 278:42352-42360.
19. Jiang M, et al. (2008) Identification and characterization of (1R,6R)-2-succinyl-6- hydroxy-2,4-cyclohexadiene-1-carboxylate synthase in the menaquinone biosynthesis of Escherichia coli. Biochemistry 47:3426-3434.
20. Overbeek R, Fonstein M, D'Souza M, Pusch GD, Maltsev N (1999) The use of gene clusters to infer functional coupling. Proc Natl Acad Sci USA 96: 2896-2901
21. Dillon SC, Bateman A (2004) The Hotdog fold: Wrapping up a superfamily of thioesterases and dehydratases. BMC Bioinf 5:109.
22. Thoden JB, Holden HM, Zhuang Z, Dunaway-Mariano D (2002) X-ray crystallographic analyses of inhibitor and substrate complexes of wild-type and mutant 4-hydroxybenzoyl-CoA thioesterase. J Biol Chem 277:27468-27476.
23. Zhuang Z, Song F, Takami H, Dunaway-Mariano D (2004) The BH1999 protein of Bacillus haloduransC-125isgentisyl-coenzymeAthioesterase. J Bacteriol 186:393-399.
24. Song F, Zhuang Z, Dunaway-Mariano D (2007) Structure-activity analysis of base and enzyme-catalyzed 4-hydroxybenzoyl coenzyme A hydrolysis. Bioorg Chem 35:1-10.
25. Dansette P, Azerad R (1970) A new intermediate in naphthoquinone and menaquinone biosynthesis. Biochem Biophys Res Commun 40:1090-1095.
26. Chang K-H, Liang P-H, Beck W, Scholten JD, Dunaway-Mariano D (1992) Isolation and characterization of the three polypeptide components of 4-chlorobenzoate dehalogenase from Pseudomonas sp. strain CBS-3. Biochemistry 31:5605-5610.
27. Roser W (1884) About phtalylderivatives (Transl. From German). II. Ber Deut Chem Ges 17:2770-2775.
28. Williams JGK (1988) Construction of specific mutations in photosystem II photosynthetic reaction centerby genetic engineering methods in Synechocystis 6803. Methods Enzymol 167:766-778.
29. Sattler SE, Cahoon EB, Coughlan SJ, DellaPenna D (2003) Characterization of tocopherol cyclases from higher plants and cyanobacteria. Evolutionary implications for tocopherol synthesis and function. Plant Physiol 132:2184-2195.
30. Oostende C,Widhalm JR, BassetGJ (2008) Detection and quantificationof vitamin K(1) quinol in leaf tissues. Phytochemistry 69:2457-2462.