{{위키데이터 속성 추적}}
{{chembox
| verifiedrevid = 477199926
| Name=(E)-4-하이드록시-3-메틸뷰트-2-엔일 피로인산<br>(''E'')-4-Hydroxy-3-methyl-but-2-enyl pyrophosphate
| ImageFile = HMB-PP.svg
| ImageSize = 190px
| ImageName = Chemical structure of HMB-PP
| ImageFile1 = HMBPP-3D-balls.png
| ImageSize1 = 240px
| ImageName1 = Ball-and-stick model, shown here as a 3- ion
| IUPACName = (''E'')-4-hydroxy-3-methylbut-2-enoxy-oxidophosphoryl phosphate
| OtherNames = (''E'')-4-hydroxy-dimethylallyl pyrophosphate<br>HDMAPP<br>(''E'')-4-Hydroxy-3-methyl-but-2-enyl diphosphate<br>HMBDP
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 15664
| ChemSpiderID = 4445244
| InChI = 1/C5H12O8P2/c1-5(4-6)2-3-12-15(10,11)13-14(7,8)9/h2,6H,3-4H2,1H3,(H,10,11)(H2,7,8,9)/b5-2+
| InChIKey = MDSIZRKJVDMQOQ-GORDUTHDBB
| SMILES1 = O=P(OP(=O)(O)O)(OC/C=C(/CO)C)O
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C5H12O8P2/c1-5(4-6)2-3-12-15(10,11)13-14(7,8)9/h2,6H,3-4H2,1H3,(H,10,11)(H2,7,8,9)/b5-2+
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = MDSIZRKJVDMQOQ-GORDUTHDSA-N
| CASNo_Ref = {{cascite|correct|??}}
| CASNo = 
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 145233
| PubChem = 21597501
| SMILES = CC(=CCOP(=O)([O-])OP(=O)([O-])[O-])CO}}
|Section2={{Chembox Properties
| C=5 | H=12 | O=8 | P=2
| Appearance = 
| Density = 
| MeltingPt = 
| BoilingPt = 
| Solubility = }}
|Section3={{Chembox Hazards
| MainHazards = 
| FlashPt = 
| AutoignitionPt = }}
}}
'''(''E'')-4-하이드록시-3-메틸뷰트-2-엔일 피로인산'''({{llang|en|(''E'')-4-hydroxy-3-methyl-but-2-enyl pyrophosphate}}, '''HMB-PP''', '''HMBPP''')은 [[아이소프레노이드]] [[생합성]]의 [[비메발론산 경로]]에서의 [[대사 중간생성물]]이다.<ref name="Rohmer">{{저널 인용| last1 = Rohmer | first1 = M | title = The discovery of a mevalonate-independent pathway for isoprenoid biosynthesis in bacteria, algae and higher plants | journal = Natural Product Reports | volume = 16 | issue = 5 | pages = 565–74 | year = 1999 | pmid = 10584331 | doi=10.1039/a709175c | last2 = Rohmer | first2 = Michel}}</ref><ref name="Poulter">{{저널 인용| last1 = Fox | first1 = DT | last2 = Poulter | first2 = CD | title = Synthesis of (E)-4-hydroxydimethylallyl diphosphate. An intermediate in the methyl erythritol phosphate branch of the isoprenoid pathway | journal = The Journal of Organic Chemistry | volume = 67 | issue = 14 | pages = 5009–10 | year = 2002 | pmid = 12098326 | doi=10.1021/jo0258453}}</ref> [[(E)-4-하이드록시-3-메틸뷰트-2-엔일 피로인산 생성효소|(''E'')-4-하이드록시-3-메틸뷰트-2-엔일 피로인산 생성효소]](HMB-PP 생성효소, IspG)는 [[2-C-메틸에리트리톨 2,4-사이클로피로인산|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 [[4-하이드록시-3-메틸뷰트-2-엔일 피로인산 환원효소]](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.<ref name="Eisenreich">{{저널 인용| last1 = Eisenreich | first1 = W | last2 = Bacher | first2 = A | last3 = Arigoni | first3 = D | last4 = Rohdich | first4 = F | title = Biosynthesis of isoprenoids via the non-mevalonate pathway | url = https://archive.org/details/sim_cellular-and-molecular-life-sciences_2004-06_61_12/page/1401 | journal = Cellular and Molecular Life Sciences | volume = 61 | issue = 12 | pages = 1401–26 | year = 2004 | pmid = 15197467 | doi = 10.1007/s00018-004-3381-z }}</ref>

(''E'')-4-하이드록시-3-메틸뷰트-2-엔일 피로인산은 말초 [[혈액]]의 주요 γδ T 세포 집단인 사람의 Vγ9/Vδ2 T 세포에 대한 생리적인 활성인자([[비펩타이드 항원]])이다. (''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.<ref>{{저널 인용|title = Activation of human γδ T cells by cytosolic interactions of BTN3A1 with soluble phosphoantigens and the cytoskeletal adaptor Periplakin|vauthors=Rhodes DA, Chen HC, Price AJ, Keeble AH, Davey MS, James LC, Eberl M, Trowsdale J|date = 2015|journal = J Immunol|doi = 10.4049/jimmunol.1401064|pmid = 25637025|access-date =|pmc=4337483|volume=194|issue=5|pages=2390–8}}</ref>

== 같이 보기 ==
* [[비메발론산 경로]]
* [[2-C-메틸에리트리톨 2,4-사이클로피로인산|2-''C''-메틸에리트리톨 2,4-사이클로피로인산]] (MEcPP)

== 각주 ==
{{각주}}

== 외부 링크 ==
* {{MeshName|4-hydroxy-3-methylbut-2-enyl+pyrophosphate}}

{{스테로이드 대사 중간생성물들}}

[[분류:생체분자]]
[[분류:물질대사]]
[[분류:유기 인산염]]
[[분류:헤미테르펜]]