Synthesis of Methylerythritol Phosphate Analogues and Their Evaluation as Alternate Substrates for IspDF and IspE from Agrobacterium tumefaciens
Autor: | Robert M. Coates, C. Dale Poulter, Marek Urbansky, Chad E. Davis, Christian Lherbet, Sergiy Krasutsky |
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Přispěvatelé: | Department of Chemistry, Synthèse et Physico-Chimie de Molécules d'Intérêt Biologique (SPCMIB), Institut de Chimie de Toulouse (ICT-FR 2599), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS) |
Rok vydání: | 2014 |
Předmět: |
Magnetic Resonance Spectroscopy
Erythritol 010402 general chemistry 01 natural sciences Article Catalysis Substrate Specificity chemistry.chemical_compound Hemiterpenes Organophosphorus Compounds Bacterial Proteins Multienzyme Complexes [CHIM]Chemical Sciences ComputingMilieux_MISCELLANEOUS Enzyme Assays chemistry.chemical_classification Sugar phosphates Molecular Structure biology 010405 organic chemistry Organic Chemistry Agrobacterium tumefaciens biology.organism_classification 0104 chemical sciences Chloroplast Phosphotransferases (Alcohol Group Acceptor) Cytosol Enzyme chemistry Biochemistry Sugar Phosphates Mevalonate pathway Bacteria |
Zdroj: | Journal of Organic Chemistry Journal of Organic Chemistry, American Chemical Society, 2014, 79 (19), pp.9170-9178. ⟨10.1021/jo501529k⟩ The Journal of Organic Chemistry |
ISSN: | 1520-6904 0022-3263 |
DOI: | 10.1021/jo501529k |
Popis: | The methylerythritol phosphate biosynthetic pathway, found in most Bacteria, some parasitic protists, and plant chloroplasts, converts D-glyceraldehyde phosphate and pyruvate to isopentenyl diphosphate (IPP) and dimethylallyl diphosphate (DMAPP), where it intersects with the mevalonate pathway found in some Bacteria, Archaea, and Eukarya, including the cytosol of plants. D-3-Methylerythritol-4-phosphate (MEP), the first pathway-specific intermediate in the pathway, is converted to IPP and DMAPP by the consecutive action of the IspD-H proteins. We synthesized five D-MEP analogues-D-erythritol-4-phosphate (EP), D-3-methylthrietol-4-phosphate (MTP), D-3-ethylerythritol-4-phosphate (EEP), D-1-amino-3-methylerythritol-4-phosphate (NMEP), and D-3-methylerythritol-4-thiolophosphate (MESP)-and studied their ability to function as alternative substrates for the reactions catalyzed by the IspDF fusion and IspE proteins from Agrobacterium tumefaciens, which covert MEP to the corresponding eight-membered cyclic diphosphate. All of the analogues, except MTP, and their products were substrates for the three consecutive enzymes. |
Databáze: | OpenAIRE |
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