52131
2-C-Methyl-D-erythritol 4-phosphate lithium salt
≥98% (TLC)
Synonym(s):
MEP
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About This Item
Empirical Formula (Hill Notation):
C5H11O7P · xLi+
CAS Number:
Molecular Weight:
214.11 (free acid basis)
UNSPSC Code:
12352106
PubChem Substance ID:
NACRES:
NA.25
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Quality Level
Assay
≥98% (TLC)
storage temp.
−20°C
SMILES string
O=P(O)(O)OC[C@H](O)[C@@](O)(C)CO.C
InChI
1S/C5H13O7P/c1-5(8,3-6)4(7)2-12-13(9,10)11/h4,6-8H,2-3H2,1H3,(H2,9,10,11)/t4-,5+/m1/s1
InChI key
XMWHRVNVKDKBRG-UHNVWZDZSA-N
Application
2-C-Methyl-D-erythritol 4-phosphate (MEP), the product of reductoisomerase IspC and first committed MEP pathway intermediate, is used to study the non-mevalonate MEP pathway for the biosynthesis of isoprenoids. MEP is used as a precursor for the synthesis of 4-diphosphocytidyl-2-C-methyl D-erythritol (CDP-ME), a key intermediate of the non-mevalonate pathway.
Biochem/physiol Actions
Metabolite intermediate specific to the non-mevalonate MEP pathway, generally found in prokaryotes, as precursor to isoprenoids as well as non-isoprenoids like vitamins. As this pathway is not present in humans, it is of interest for the development of bacterium-specific drugs in the search for treatments of infectious diseases.
Packaging
Bottomless glass bottle. Contents are inside inserted fused cone.
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Certificates of Analysis (COA)
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Tomohisa Kuzuyama et al.
Proceedings of the Japan Academy. Series B, Physical and biological sciences, 88(3), 41-52 (2012-03-28)
Isoprenoids are a diverse group of molecules found in all organisms, where they perform such important biological functions as hormone signaling (e.g., steroids) in mammals, antioxidation (e.g., carotenoids) in plants, electron transport (e.g., ubiquinone), and cell wall biosynthesis intermediates in
J Kipchirchir Bitok et al.
ACS chemical biology, 7(10), 1702-1710 (2012-07-31)
There is significant progress toward understanding catalysis throughout the essential MEP pathway to isoprenoids in human pathogens; however, little is known about pathway regulation. The present study begins by testing the hypothesis that isoprenoid biosynthesis is regulated via feedback inhibition
Sinéad Heuston et al.
Microbiology (Reading, England), 158(Pt 6), 1389-1401 (2012-04-03)
Isoprenoid biosynthesis is essential for cell survival. Over 35 000 isoprenoid molecules have been identified to date in the three domains of life (bacteria, archaea and eukaryotes), and these molecules are involved in a wide variety of vital biological functions. Isoprenoids
Andréa Hemmerlin et al.
Progress in lipid research, 51(2), 95-148 (2011-12-27)
When compared to other organisms, plants are atypical with respect to isoprenoid biosynthesis: they utilize two distinct and separately compartmentalized pathways to build up isoprene units. The co-existence of these pathways in the cytosol and in plastids might permit the
Sina I Odejinmi et al.
Tetrahedron, 68(43), 8937-8941 (2012-10-11)
2-C-methyl-D-erythritol-4-phosphate (MEP) is a key chemical intermediate of the non-mevalonate pathway for isoprenoid biosynthesis employed by many pathogenic microbes. MEP is also the precursor for the synthesis of 4-diphosphocytidyl-2-C-methyl D-erythritol (CDP-ME), another key intermediate of the non-mevalonate pathway. As this
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