(E)-4-Hydroxy-3-methyl-but-2-enyl pyrophosphate (original) (raw)
Le (E)-4-hydroxy-3-méthyl-but-2-ényl-pyrophosphate (HMB-PP) est un intermédiaire de la voie du méthylérythritol phosphate (voie « non mévalonique ») de biosynthèse des isoprénoïdes. C'est une voie métabolique essentielle chez les plantes, la plupart des bactéries pathogènes, par exemple chez Mycobacterium tuberculosis, ainsi que chez les protozoaires du genre Plasmodium, parasites du paludisme, mais pas chez les archées et les animaux, ce qui permet d'envisager des applications dans la recherche sur les antibiotiques, les antipaludéens et les herbicides.
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| dbo:abstract | (E)-4-Hydroxy-3-methyl-but-2-enyl pyrophosphate (HMBPP or HMB-PP) is an intermediate of the MEP pathway (non-mevalonate pathway) of isoprenoid biosynthesis. The enzyme HMB-PP synthase (GcpE, IspG) catalyzes the conversion of 2-C-methyl-D-erythritol 2,4-cyclodiphosphate (MEcPP) into HMB-PP. HMB-PP is then converted further to isopentenyl pyrophosphate (IPP) and dimethylallyl pyrophosphate (DMAPP) by HMB-PP reductase (LytB, IspH). HMB-PP is an essential metabolite in most pathogenic bacteria including Mycobacterium tuberculosis as well as in malaria parasites, but is absent from the human host. HMB-PP is the physiological activator ("phosphoantigen") for human Vγ9/Vδ2 T cells, the major γδ T cell population in peripheral blood. With a bioactivity of 0.1 nM it is 10,000-10,000,000 times more potent than any other natural compound, such as IPP or alkyl amines. HMB-PP functions in this capacity by binding the B30.2 domain of BTN3A1. (en) Le (E)-4-hydroxy-3-méthyl-but-2-ényl-pyrophosphate (HMB-PP) est un intermédiaire de la voie du méthylérythritol phosphate (voie « non mévalonique ») de biosynthèse des isoprénoïdes. C'est une voie métabolique essentielle chez les plantes, la plupart des bactéries pathogènes, par exemple chez Mycobacterium tuberculosis, ainsi que chez les protozoaires du genre Plasmodium, parasites du paludisme, mais pas chez les archées et les animaux, ce qui permet d'envisager des applications dans la recherche sur les antibiotiques, les antipaludéens et les herbicides. (fr) (E)-4-ヒドロキシ-3-メチル-2-ブテニル二リン酸（(E)-4-ヒドロキシ-3-メチル-2-ブテニルにリンさん、HMB-PP、HMBPP）もしくは(E)-4-ヒドロキシジメチルアリル二リン酸（(E)-4-ヒドロキシジメチルアリル二リン酸、HDMAPP）は、イソプレノイド生合成の非メバロン酸経路の中間生成物である。 (ja) (E)-4-하이드록시-3-메틸뷰트-2-엔일 피로인산(영어: (E)-4-hydroxy-3-methyl-but-2-enyl pyrophosphate, HMB-PP, HMBPP)은 아이소프레노이드 생합성의 비메발론산 경로에서의 대사 중간생성물이다. (HMB-PP 생성효소, IspG)는 2-C-메틸에리트리톨 2,4-사이클로피로인산(MEcPP)을 (E)-4-하이드록시-3-메틸뷰트-2-엔일 피로인산(HMB-PP)으로 전환시키는 것을 촉매한다. (E)-4-하이드록시-3-메틸뷰트-2-엔일 피로인산(HMB-PP)은 (HMB-PP 환원효소, IspH)에 의해 아이소펜테닐 피로인산(IPP)과 다이메틸알릴 피로인산(DMAPP)으로 전환된다. (E)-4-하이드록시-3-메틸뷰트-2-엔일 피로인산은 결핵균(Mycobacterium tuberculosis)을 비롯한 대부분의 병원성 세균에서 필수적인 대사산물이지만 사람에는 존재하지 않는다. (E)-4-하이드록시-3-메틸뷰트-2-엔일 피로인산은 말초 혈액의 주요 γδ T 세포 집단인 사람의 Vγ9/Vδ2 T 세포에 대한 생리적인 활성인자이다. (E)-4-하이드록시-3-메틸뷰트-2-엔일 피로인산은 0.1 nM의 극소 농도로도 생체 활성을 가지며 아이소펜테닐 피로인산(IPP)이나 알킬 아민과 같은 다른 천연 화합물보다 10,000배~10,000,000배 더 강력하다. (E)-4-하이드록시-3-메틸뷰트-2-엔일 피로인산은 BTN3A1의 B30.2 도메인에 결합하여 기능을 수행한다. (ko) |
| dbo:alternativeName | HDMAPP (en) HMBDP (en) (E)-4-Hydroxy-3-methyl-but-2-enyl diphosphate (en) (E)-4-hydroxy-dimethylallyl pyrophosphate (en) |
| dbo:iupacName | (E)-4-hydroxy-3-methylbut-2-enoxy-oxidophosphoryl phosphate (en) |
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| dbo:wikiPageWikiLink | dbc:Biomolecules dbc:Hemiterpenes dbc:Metabolism dbc:Organophosphates dbr:Malaria dbr:2-C-Methyl-D-erythritol-2,4-cyclopyrophosphate dbr:4-Hydroxy-3-methylbut-2-enyl_diphosphate_reductase dbr:4-hydroxy-3-methylbut-2-en-1-yl_diphosphate_synthase dbr:Isopentenyl_pyrophosphate dbr:Non-peptidic_antigen dbr:Dimethylallyl_pyrophosphate dbr:Mycobacterium_tuberculosis dbr:Non-mevalonate_pathway dbr:BTN3A1 dbr:Gamma/delta_T_cells dbr:Phosphoantigen dbr:Vg9/Vd2_T_cells |
| dbp:imagefile | HMB-PP.svg (en) HMBPP-3D-balls.png (en) |
| dbp:imagename | Ball-and-stick model, shown here as a 3- ion (en) Chemical structure of HMB-PP (en) |
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| dbp:othernames | -4 (xsd:integer) HDMAPP (en) HMBDP (en) |
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| dcterms:subject | dbc:Biomolecules dbc:Hemiterpenes dbc:Metabolism dbc:Organophosphates |
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| rdfs:comment | Le (E)-4-hydroxy-3-méthyl-but-2-ényl-pyrophosphate (HMB-PP) est un intermédiaire de la voie du méthylérythritol phosphate (voie « non mévalonique ») de biosynthèse des isoprénoïdes. C'est une voie métabolique essentielle chez les plantes, la plupart des bactéries pathogènes, par exemple chez Mycobacterium tuberculosis, ainsi que chez les protozoaires du genre Plasmodium, parasites du paludisme, mais pas chez les archées et les animaux, ce qui permet d'envisager des applications dans la recherche sur les antibiotiques, les antipaludéens et les herbicides. (fr) (E)-4-ヒドロキシ-3-メチル-2-ブテニル二リン酸（(E)-4-ヒドロキシ-3-メチル-2-ブテニルにリンさん、HMB-PP、HMBPP）もしくは(E)-4-ヒドロキシジメチルアリル二リン酸（(E)-4-ヒドロキシジメチルアリル二リン酸、HDMAPP）は、イソプレノイド生合成の非メバロン酸経路の中間生成物である。 (ja) (E)-4-Hydroxy-3-methyl-but-2-enyl pyrophosphate (HMBPP or HMB-PP) is an intermediate of the MEP pathway (non-mevalonate pathway) of isoprenoid biosynthesis. The enzyme HMB-PP synthase (GcpE, IspG) catalyzes the conversion of 2-C-methyl-D-erythritol 2,4-cyclodiphosphate (MEcPP) into HMB-PP. HMB-PP is then converted further to isopentenyl pyrophosphate (IPP) and dimethylallyl pyrophosphate (DMAPP) by HMB-PP reductase (LytB, IspH). HMB-PP is an essential metabolite in most pathogenic bacteria including Mycobacterium tuberculosis as well as in malaria parasites, but is absent from the human host. (en) (E)-4-하이드록시-3-메틸뷰트-2-엔일 피로인산(영어: (E)-4-hydroxy-3-methyl-but-2-enyl pyrophosphate, HMB-PP, HMBPP)은 아이소프레노이드 생합성의 비메발론산 경로에서의 대사 중간생성물이다. (HMB-PP 생성효소, IspG)는 2-C-메틸에리트리톨 2,4-사이클로피로인산(MEcPP)을 (E)-4-하이드록시-3-메틸뷰트-2-엔일 피로인산(HMB-PP)으로 전환시키는 것을 촉매한다. (E)-4-하이드록시-3-메틸뷰트-2-엔일 피로인산(HMB-PP)은 (HMB-PP 환원효소, IspH)에 의해 아이소펜테닐 피로인산(IPP)과 다이메틸알릴 피로인산(DMAPP)으로 전환된다. (E)-4-하이드록시-3-메틸뷰트-2-엔일 피로인산은 결핵균(Mycobacterium tuberculosis)을 비롯한 대부분의 병원성 세균에서 필수적인 대사산물이지만 사람에는 존재하지 않는다. (ko) |
| rdfs:label | (E)-4-Hydroxy-3-methyl-but-2-enyl pyrophosphate (en) (E)-4-Hydroxy-3-méthyl-but-2-ényl-pyrophosphate (fr) (E)-4-하이드록시-3-메틸뷰트-2-엔일 피로인산 (ko) (E)-4-ヒドロキシ-3-メチル-2-ブテニル二リン酸 (ja) |
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