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07841

Sigma-Aldrich

(R)-Mevalonic acid 5-phosphate lithium salt

95% (TLC)

Synonym(s):

(R)-3-Hydroxy-3-methyl-5-phosphonooxy-pentanoic acid lithium salt, (R)-5-Phosphomevalonate lithium salt, R-MVAP-Li

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About This Item

Empirical Formula (Hill Notation):
C6H13O7P · xLi+
CAS Number:
73566-35-5
Molecular Weight:
228.14 (free acid basis)
UNSPSC Code:
12352106
NACRES:
NA.25

Quality Level

100

assay

95% (TLC)

optical activity

[α]/D -3.2±0.5°, c = 0.1 in 0.2 M HCl

storage temp.

−20°C

SMILES string

[P](=O)([O-])([O-])OCC[C@@](O)(CC(=O)[O-])C

InChI

1S/C6H13O7P/c1-6(9,4-5(7)8)2-3-13-14(10,11)12/h9H,2-4H2,1H3,(H,7,8)(H2,10,11,12)/p-3/t6-/m1/s1

InChI key

OKZYCXHTTZZYSK-ZCFIWIBFSA-K

Related Categories

Application

Mevalonic acid 5-phosphate (M5P) may be used as a reference material in assays for the separation or detection of mevalonic acid 5-phosphate. Mevalonic acid 5-phosphate is the immediate precursor of isopentenyl pyrophosphate (IPP) and the mevalonate pathway which leads to isoprenoid biosynthesis. Mevalonic acid 5-phosphate may be used as a substrate to identify and characterize phosphomevalonate kinase(s).

Biochem/physiol Actions

Metabolite of the mevalonate pathway, which plays a key role in the biosynthesis of sterols, dolichol, heme and ubiquinone. Of interest for research in the disease areas oncology, autoimmune diseases, artherosclerosis and Alzheimer disease, as well as for inherited deficiencies of mevalonate kinase.

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

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Certificates of Analysis (COA)

Lot/Batch Number
BCBT5717
1426964V
1426964

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Molecular docking and NMR binding studies to identify novel inhibitors of human phosphomevalonate kinase.
Boonsri P, Neumann TS, et al.
Biochemical and Biophysical Research Communications (2012)
Timothy J Herdendorf et al.
Biochemistry, 45(10), 3235-3242 (2006-03-08)
Phosphomevalonate kinase (PMK) catalyzes a key step in isoprenoid/sterol biosynthesis, converting mevalonate 5-phosphate and ATP to mevalonate 5-diphosphate and ADP. To expedite functional and structural study of this enzyme, an expression plasmid encoding His-tagged human PMK has been constructed and
Andrew L Olson et al.
Journal of the American Chemical Society, 132(7), 2102-2103 (2010-02-02)
Phosphomevalonate kinase (PMK) catalyzes phosphoryl transfer from adenosine triphosphate (ATP) to mevalonate 5-phosphate (M5P) on the pathway for synthesizing cholesterol and other isoprenoids. To permit this reaction, its substrates must be brought proximal, which would result in a significant and
Andrew L Olson et al.
Proteins, 75(1), 127-138 (2008-09-19)
Phosphomevalonate kinase (PMK) catalyzes an essential step in the mevalonate pathway, which is the only pathway for synthesis of isoprenoids and steroids in humans. PMK catalyzes transfer of the gamma-phosphate of ATP to mevalonate 5-phosphate (M5P) to form mevalonate 5-diphosphate.

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