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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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$214.00
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5 MG
$214.00
25 MG
$824.00

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

$214.00

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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.[1]

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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000417331
0000417333
0000411626
0000411626
0000417333

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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
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
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
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
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.
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