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F8682

Sigma-Aldrich

Fosmidomycin sodium salt hydrate

≥95% (NMR)

Synonym(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

Empirical Formula (Hill Notation):
C4H10NO5P · xNa+ · yH2O
CAS Number:
66508-53-0
Molecular Weight:
183.10 (anhydrous free acid basis)
MDL number:
MFCD00865023
UNSPSC Code:
12352200
NACRES:
NA.77

Quality Level

100

Assay

≥95% (NMR)

form

powder

storage condition

desiccated

color

white to beige

solubility

H2O: 20 mg/mL, clear

storage temp.

−20°C

SMILES string

[P](=O)(O)(O)CCCN(O)C=O

InChI

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

InChI key

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.

Biochem/physiol Actions

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).

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

监管及禁止进口产品

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Certificates of Analysis (COA)

Lot/Batch Number
0000411626
0000411626
0000117637
0000117638
0000117637

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Miguel Lanaspa et al.
Antimicrobial agents and chemotherapy, 56(6), 2923-2928 (2012-03-21)
The combination of fosmidomycin and clindamycin (F/C) is effective in adults and older children for the treatment of malaria and could be an important alternative to existing artemisinin-based combinations (ACTs) if proven to work in younger children. We conducted an
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
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
Tami L Sivy et al.
Bioscience, biotechnology, and biochemistry, 75(12), 2376-2383 (2011-12-08)
The mevalonic acid (MVA) and methylerythritol phosphate (MEP) pathways for isoprenoid biosynthesis both culminate in the production of the two-five carbon prenyl diphosphates: dimethylallyl diphosphate (DMAPP) and isopentenyl diphosphate (IPP). These are the building blocks for higher isoprenoids, including many
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