| Identification | Back Directory | [Name]
PHOSPHORAMIDON | [CAS]
119942-99-3 | [Synonyms]
NSC 694280
PHOSPHORAMIDON
PhosphoraMidon sodiuM
Phophoramidon disodium
PHOSPHATIDYL DIPEPTIDE
PhosphoraMidon disodiuM sa
Phosphoramidon disodium salt
PhosphoraMidon research grade
PhosphoD23-RAMidon disodiuM salt
N-(ALPHA-RHAMNOPYRANOSYLPHOS.)-L-LEUCYL&
Phosphoramidon disodium salt, ≥97% (HPLC)
N-(α-Rhamnopyranosyloxyhydroxyphosphinyl)-Leu-Trp
N-(A-RHAMNOPYRANOSYLOXYHYDROXYPHOSPHINYL)-LEU-TRP
PHOSPHORAMIDON SODIUM SALT, FROM MICROBIAL SOURCE
N-(A-rhamnopyranosyloxyhydroxy-*phosphinyl)-leu-T
N-(ALPHA-RHAMNOPYRANOSYLOXYHYDROXYPHOSPHINYL)-LEU-TRP-OH
N-(alpha-rhamnopyranosylphos.)-L-leucyl-L-tryp. disod. salt
n-(α-rhamno-pyranosyl-oxy-hydroxy-phosphinyl)-leu-trp disodium salt
N-(α-Rhamnopyranosylphosphono)-L-leucyl-L-tryptophan disodium salt
N-(alpha-Rhamnopyranosyloxyhydroxyphosphinyl)-Leu-Trp disodium salt
N-[[(6-Deoxy-a-L-mannopyranosyl)oxy]hydroxyphosphinyl]-L-leucyl- L-tryptophan Disodium Salt
L-Tryptophan,N-[[(6-deoxy-a-L-mannopyranosyl)oxy]hydroxyphosphinyl]-L-leucyl-,sodium salt (9CI)
disodium,3-(1H-indol-3-yl)-2-[[4-methyl-2-[[oxido-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxyphosphoryl]amino]pentanoyl]amino]propanoate
N-(α-Rhamnopyranosylphosphono)-L-leucyl-L-tryptophan disodium salt, N-(α-Rhamnopyranosyloxyhydroxyphosphinyl)-Leu-Trp disodium salt | [EINECS(EC#)]
252-996-3 | [Molecular Formula]
C23H32N3O10P.2Na | [MDL Number]
MFCD00080262 | [MOL File]
119942-99-3.mol | [Molecular Weight]
587.47 |
| Chemical Properties | Back Directory | [storage temp. ]
−20°C
| [solubility ]
H2O: 1 mM Stock solution stable for 1 month at –20° C.
| [form ]
Solid | [color ]
White to pale yellow | [biological source]
Streptomyces sp. | [Water Solubility ]
H2O: 50mg/mL | [BRN ]
8105669 | [Stability:]
Stable for 2 years from date of purchase as supplied. Solutions in DMSO, methanol, or distilled water may be stored at -20°C for up to 2 months. |
| Hazard Information | Back Directory | [Description]
Phosphoramidon (119942-99-3) inhibits neutral endopeptidase 24.11 (NEP; Neprilysin; EC 3.4.24.11), Ki=2 nM.1?Also inhibits neprilysin 2 (Ki~2 nM).2?Also inhibits endothelin-converting enzyme (IC50?= 0.68 μM).3?Induces a dramatic increase in amyloid-beta levels in rodents.4 | [Uses]
An endothelin-converting enzyme inhibitor, attenuates lipopolysaccharide-induced acute lung injury. | [General Description]
Phosphoramidon [N-(α-rhamnopyranosyl-oxyhydroxyphosphinyl)-Leu-Trp] is a competitive inhibitor of several soluble zinc metalloproteases. Phosphoramidate is produced naturally by Streptomyces?tanashiensis. | [Biological Activity]
Inhibits neutral endopeptidase 24.11 (NEP, neprilysin; EC 3.4.24.11) (Ki=2nM), a cell surface zinc metalloprotease which cleaves bioactive peptides such as bradykinin, neurotensin, and enkephalin. Also inhibits neprilysin 2 (Ki~2nM). Potent inhibitor of endothelin-converting enzyme (ECE) (IC50=0.68μM). | [Biochem/physiol Actions]
Phosphoramidon can inhibit ZMPSTE24, an integral membrane protein zinc metalloprotease. It is capable of blocking thermolysin. | [References]
1) Stephenson and Kenny et al. (1987),?The hydrolysis of alpha-human atrial natriuretic peptide by pig kidney microvillar membranes is initiated by endopeptidase-24.11.; Biochem. J.,?243?183.
2) Rose?et al.?(2002),?Cell-specific activity of neprilysin 2 isoforms and enzymic specificity compared with neprilysin; Biochem. J.,?363?697
3) Ahn?et al.?(1998),?Soluble human endothelin-converting enzyme-1: expression, purification, and demonstration of pronounced pH sensitivity; Arch. Biochem. Biphys.,?359?258
4) Marr and Hafez (2014),?Amyloid-beta and Alzheimer’s disease: the role of neprilysin-2 in amyloid-beta clearance; Front. Aging Neurosci.,?6?187 |
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