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79849

Sigma-Aldrich

(±)-Mevalonic acid 5-phosphate lithium salt hydrate

95% (TLC)

Synonym(s):

(±)-MVAP-Li, rac-5-Phosphomevalonate lithium salt

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About This Item

Empirical Formula (Hill Notation):
C6H13O7P · xLi+ · yH2O
Molecular Weight:
228.14 (free acid basis)
UNSPSC Code:
12352204
PubChem Substance ID:
329768653
NACRES:
NA.32

Quality Level

100

Assay

95% (TLC)

form

powder or crystals

impurities

≤15% water

relevant disease(s)

Alzheimer′s disease; autoimmune diseases

storage temp.

2-8°C

SMILES string

OC(CC(C)(O)CCOP(O)(O)=O)=O.[H]O[H].[Li+]

InChI

1S/C6H13O7P.3Li.H2O/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);;;;1H2/q;3*+1;/p-3

InChI key

VYTYNAKRCDFACM-UHFFFAOYSA-K

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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D N Skilleter et al.
The Biochemical journal, 124(2), 407-417 (1971-09-01)
1. Phosphomevalonate kinase and 5-pyrophosphomevalonate decarboxylase have been purified from the freeze-dried latex serum of the commercial rubber tree Hevea brasiliensis. 2. The phosphomevalonate kinase was acid- and heat-labile and required the presence of a thiol to maintain activity. 3.
Inhibition of hepatic cholesterol biosynthesis by 3,5-dihydroxy-3,4,4-trimethylvaleric acid and its site of action.
F H Hulcher
Archives of biochemistry and biophysics, 146(2), 422-427 (1971-10-01)
John L Andreassi et al.
Biochemistry, 48(27), 6461-6468 (2009-06-03)
The galacto-, homoserine-, mevalonate-, phosphomevalonate-kinase (GHMP) superfamily encompases a wide-range of protein function. Three members of the family (mevalonate kinase, phosphomevalonate kinase, and diphosphomevalonate decarboxylase) comprise the mevalonate pathway found in S. pneumoniae and other organisms. We have determined the
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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