ArticleProceedings of the National Academy of Sciences of the United States of America2009
A dedicated thioesterase of the Hotdog-fold family is required for the biosynthesis of the naphthoquinone ring of vitamin K1.
Article in Proceedings of the National Academy of Sciences of the United States of America, 2009. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 29 papers.
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Who cites it
29 citing papers in PubMed, 62 citations in OpenAlex.
- Gut microbiota of liver transplantation recipients.Scientific reports · 2017Trial
- Vitamin K in photosynthetic organisms.Planta · 2026Review
- Quinol C-methyltransferases from extant species of early cyanobacterial lineages shed light on the emergence of plastoquinone in oxygenic phototrophs.Photosynthesis research · 2025Article
- The evolution of strictly monofunctional naphthoquinol C-methyltransferases is vital in cyanobacteria and plastids.The Plant cell · 2023Article
- Boosting vegetation, biochemical constituents, grain yield and anti-cancer performance of cultivated oat (Avena sativa L) in calcareous soil using oat extracts coated inside nanocarriers.BMC plant biology · 2022Article
- Thioesterase enzyme families: Functions, structures, and mechanisms.Protein science : a publication of the Protein Society · 2022Article
- Inferred Subcellular Localization of Peroxisomal Matrix Proteins ofFrontiers in plant science · 2022Article
- Bioactive Metabolites Produced by Cyanobacteria for Growth Adaptation and Their Pharmacological Properties.Biology · 2021Review
- Evolution of Ycf54-independent chlorophyll biosynthesis in cyanobacteria.Proceedings of the National Academy of Sciences of the United States of America · 2021Article
- Allosteric regulation of menaquinone (vitamin KThe Journal of biological chemistry · 2020Article
- Prenylquinones in Human Parasitic Protozoa: Biosynthesis, Physiological Functions, and Potential as Chemotherapeutic Targets.Molecules (Basel, Switzerland) · 2019Review
- Completion of the cytosolic post-chorismate phenylalanine biosynthetic pathway in plants.Nature communications · 2019Article
- Isolation and characterization of mutants corresponding to the MENA, MENB, MENC and MENE enzymatic steps of 5'-monohydroxyphylloquinone biosynthesis in Chlamydomonas reinhardtii.The Plant journal : for cell and molecular biology · 2017Article
- AnFrontiers in microbiology · 2017Article
- A Methyl 4-Oxo-4-phenylbut-2-enoate withACS infectious diseases · 2016Article
- Biosynthesis and molecular actions of specialized 1,4-naphthoquinone natural products produced by horticultural plants.Horticulture research · 2016Review
- Genomic Analysis of the Human Gut Microbiome Suggests Novel Enzymes Involved in Quinone Biosynthesis.Frontiers in microbiology · 2016Article
- Divergence of substrate specificity and function in the Escherichia coli hotdog-fold thioesterase paralogs YdiI and YbdB.Biochemistry · 2014Article
- The futalosine pathway played an important role in menaquinone biosynthesis during early prokaryote evolution.Genome biology and evolution · 2014Article
- Chlamydia exploit the mammalian tryptophan-depletion defense strategy as a counter-defensive cue to trigger a survival state of persistence.Frontiers in cellular and infection microbiology · 2014Review
Corrections and comments
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Authors and funding
4 authors at 1 institution in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Phylloquinone (vitamin K(1)) is a bipartite molecule that consists of a naphthoquinone ring attached to a phytyl side chain. The coupling of these 2 moieties depends on the hydrolysis of the CoA thioester of 1,4-dihydroxy-2-naphthoate (DHNA), which forms the naphthalenoid backbone. It is not known whether such a hydrolysis is enzymatic or chemical. In this study, comparative genomic analyses identified orthologous genes of unknown function that in most species of cyanobacteria cluster with predicted phylloquinone biosynthetic genes. The encoded approximately 16-kDa proteins display homology with some Hotdog domain-containing CoA thioesterases that are involved in the catabolism of 4-hydroxybenzoyl-CoA and gentisyl-CoA (2,5-dihydroxybenzoyl-CoA) in certain soil-dwelling bacteria. The Synechocystis ortholog, encoded by gene slr0204, was expressed as a recombinant protein and was found to form DHNA as reaction product. Unlike its homologs in the Hotdog domain family, Slr0204 showed strict substrate specificity. The Synechocystis slr0204 knockout was devoid of DHNA-CoA thioesterease activity and accumulated DHNA-CoA. As a result, knockout cells contained 13-fold less phylloquinone than their wild-type counterparts and displayed the typical photosensitivity to high light associated to phylloquinone deficiency in cyanobacteria.
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