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Merck

F8682

Sigma-Aldrich

Fosmidomycin sodium salt hydrate

≥95% (NMR)

Sinónimos:

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

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About This Item

Fórmula empírica (notación de Hill):
C4H10NO5P · xNa+ · yH2O
Número de CAS:
Peso molecular:
183.10 (anhydrous free acid basis)
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

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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


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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)
Anne-Sophie Messiaen et al.
International journal of antimicrobial agents, 38(3), 261-264 (2011-07-05)
The Burkholderia cepacia complex (BCC) is a group of 17 closely related opportunistic pathogens that are able to infect the respiratory tract of cystic fibrosis patients. BCC bacteria are intrinsically resistant to many antibiotics and are therefore difficult to eradicate.
Brian Bae et al.
The Journal of biological chemistry, 286(41), 36132-36141 (2011-08-26)
The enzyme FrbF from Streptomyces rubellomurinus has attracted significant attention due to its role in the biosynthesis of the antimalarial phosphonate FR-900098. The enzyme catalyzes acetyl transfer onto the hydroxamate of the FR-900098 precursors cytidine 5'-monophosphate-3-aminopropylphosphonate and cytidine 5'-monophosphate-N-hydroxy-3-aminopropylphosphonate. Despite
Matthew A DeSieno et al.
Chemical communications (Cambridge, England), 47(36), 10025-10027 (2011-08-11)
The Fe(II) and α-ketoglutarate-dependent hydroxylase FrbJ was previously demonstrated to utilize FR-900098 synthesizing a second phosphonate FR-33289. Here we assessed its ability to hydroxylate other possible substrates, generating a library of potential antimalarial compounds. Through a series of bioassays and

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