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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:
Molecular Weight:
183.10 (anhydrous free acid basis)
MDL number:
UNSPSC Code:
12352200
NACRES:
NA.77

Quality Level

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

Related Categories

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.
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


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Jordi Pérez-Gil et al.
The Journal of biological chemistry, 287(19), 15803-15809 (2012-03-24)
Most bacteria use the 2-C-methyl-D-erythritol 4-phosphate (MEP) pathway for the synthesis of their essential isoprenoid precursors. The absence of the MEP pathway in humans makes it a promising new target for the development of much needed new and safe antimicrobial
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Fosmidomycin derivatives in which the hydroxamic acid group has been replaced by several bidentate chelators as potential hydroxamic alternatives were prepared and tested against the DXR from Escherichia coli.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
Sarah Ponaire et al.
European journal of medicinal chemistry, 51, 277-285 (2012-03-13)
Since Mycobacterium tuberculosis sets up several multiple anti-tuberculosis drug resistance mechanisms, development of new drugs with innovative target is urgent. The methylerythritol phosphate pathway (MEP) involved in the biosynthesis of essential metabolites for the survival of mycobacteria, represents such a
The expression of 1-deoxyhezylolose 5-phosphate reductase isomerase and its relation with monotropene carvacrol biosynthesis in Khuzestan Satureja plant
Ramak P, et al.
Journal of Plant Biology, 27(4), 622-634 (2015)
Jan-Ytzen van der Meer et al.
Natural product reports, 29(7), 721-728 (2012-05-05)
Due to the increase in resistance of Plasmodium spp. against available antimalarials, there is a need for new, effective and innovative drugs. The non-mevalonate pathway for the biosynthesis of the universal isoprenoid precursors, which is absent in humans, is suggested

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