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F8682

Sigma-Aldrich

Fosmidomycin sodium salt hydrate

≥95% (NMR)

Synonyme(s) :

(3-(Formylhydroxyamino)propyl)phosphonic acid sodium salt, (3-(N-Hydroxyformamido)propyl)phosphonic acid sodium salt, FR 31564

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About This Item

Formule empirique (notation de Hill):
C4H10NO5P · xNa+ · yH2O
Numéro CAS:
66508-53-0
Poids moléculaire :
183.10 (anhydrous free acid basis)
Code UNSPSC :
12352200
Nomenclature NACRES :
NA.77

Niveau de qualité

100

Pureté

≥95% (NMR)

Forme

powder

Conditions de stockage

desiccated

Couleur

white to beige

Solubilité

H2O: 20 mg/mL, clear

Température de stockage

−20°C

InChI

1S/C4H10NO5P/c6-4-5(7)2-1-3-11(8,9)10/h4,7H,1-3H2,(H2,8,9,10)

Clé InChI

GJXWDTUCERCKIX-UHFFFAOYSA-N

Application

Fosmidomycin sodium salt hydrate has been used as an inhibitor of 1-deoxy-D-xylulose 5-phosphate reductoisomerase in a study to determine monotropin carvacrol biosynthesis in Satureja khuzistanica plant.

Actions biochimiques/physiologiques

Fosmidomycin is an inhibitor of 1-deoxy-D-xylulose 5-phosphate reductoisomerase (DXR) (MEP synthase): an antimalarial compound. 1-deoxy-D-xylulose 5-phosphate reductoisomerase (DXR) is an enzyme involved in the first step in the nonmevalonate pathway for isoprenoid biosynthesis in Gram-negative, Gram-positive bacteria, plants, and the parasite causing the most virulent form of malaria, Plasmodium falciparum (Mammals produce isoprenoids via the mevalonate pathway).

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Certificats d'analyse (COA)

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USP

USP

1286322

Fosfomycin tromethamine

Lovastatin United States Pharmacopeia (USP) Reference Standard

USP

1370600

Lovastatin

Lovastatin Pharmaceutical Secondary Standard; Certified Reference Material

Supelco

PHR1285

Lovastatin

Lovastatin European Pharmacopoeia (EP) Reference Standard

L0790000

Lovastatin

Karin Brücher et al.
Journal of medicinal chemistry, 55(14), 6566-6575 (2012-06-27)
Specific inhibition of enzymes of the non-mevalonate pathway is a promising strategy for the development of novel antiplasmodial drugs. α-Aryl-substituted β-oxa isosteres of fosmidomycin with a reverse orientation of the hydroxamic acid group were synthesized and evaluated for their inhibitory
Christoph T Behrendt et al.
Journal of medicinal chemistry, 54(19), 6796-6802 (2011-08-27)
Reverse hydroxamate-based inhibitors of IspC, a key enzyme of the non-mevalonate pathway of isoprenoid biosynthesis and a validated antimalarial target, were synthesized and biologically evaluated. The binding mode of one derivative in complex with EcIspC and a divalent metal ion
Emily R Jackson et al.
Current topics in medicinal chemistry, 12(7), 706-728 (2012-01-31)
Isoprene biosynthesis is an essential component of metabolism. Two pathways are known for the production of five-carbon (isoprene) intermediates: the mevalonate and nonmevalonate pathways. As many pathogenic organisms rely exclusively on the nonmevalonate pathway (NMP) for isoprenoids and humans do
Robert R Junker et al.
Journal of chemical ecology, 37(12), 1323-1331 (2011-12-14)
In their natural environment, plants are synchronously confronted with mutualists and antagonists, and thus benefit from signals that contain messages for both functional groups of interaction partners. Floral scents are complex blends of volatiles of different chemical classes, including benzenoids
Catherine Zinglé et al.
Bioorganic & medicinal chemistry letters, 22(21), 6563-6567 (2012-10-03)
Fosmidomycin derivatives in which the hydroxamic acid group has been replaced by several bidentate chelators as potential hydroxamic alternatives were prepared and tested against the DXR from Escherichia coli. These results illustrate the predominant role of the hydroxamate functional group
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