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Key Documents

52131

Sigma-Aldrich

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

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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
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
Hyungjin Eoh et al.
Tuberculosis (Edinburgh, Scotland), 89(1), 1-11 (2008-09-17)
Tuberculosis (TB) is still a major public health problem, compounded by the human immunodeficiency virus (HIV)-TB co-infection and recent emergence of multidrug-resistant (MDR) and extensively drug resistant (XDR)-TB. Novel anti-TB drugs are urgently required. In this context, the 2C-methyl-d-erythritol 4-phosphate

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