119942-99-3

Basic information

• Product Name: PHOSPHORAMIDON
• Synonyms: N-(A-RHAMNOPYRANOSYLOXYHYDROXYPHOSPHINYL)-LEU-TRP;N-(ALPHA-RHAMNOPYRANOSYLOXYHYDROXYPHOSPHINYL)-LEU-TRP-OH;PHOSPHORAMIDON;N-(alpha-rhamnopyranosylphos.)-L-leucyl-L-tryp. disod. salt;N-(A-rhamnopyranosyloxyhydroxy-*phosphinyl)-leu-T;N-(ALPHA-RHAMNOPYRANOSYLPHOS.)-L-LEUCYL&;PHOSPHATIDYL DIPEPTIDE;n-(α-rhamno-pyranosyl-oxy-hydroxy-phosphinyl)-leu-trp disodium salt
• CAS NO: 119942-99-3
• Molecular Formula: C23H32N3O10P.2Na
• Molecular Weight: 587.47
• EINECS: 252-996-3
• Product Categories: Chiral Reagents;Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals;Phosphorylating and Phosphitylating Agents;Pepetides;peptides;inhibitor
• Mol File: 119942-99-3.mol
• Article Data: 0

Chemical Properties

• Appearance: White to pale yellow/Solid
• Storage Temp.: −20°C
• Solubility: H2O: 1 mM Stock solution stable for 1 month at –20&#
• 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.
• BRN: 8105669
• CAS DataBase Reference: PHOSPHORAMIDON(CAS DataBase Reference)
• NIST Chemistry Reference: PHOSPHORAMIDON(119942-99-3)
• EPA Substance Registry System: PHOSPHORAMIDON(119942-99-3)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• F: 10-21
• Hazardous Substances Data: 119942-99-3(Hazardous Substances Data)

Usage

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

Different sources of media describe the Uses of 119942-99-3 differently. You can refer to the following data:
1. An endothelin-converting enzyme inhibitor, attenuates lipopolysaccharide-induced acute lung injury.
2. Phosphoramidon is an inhibitor of NEP 24.11 and NEP2. It is an inhibitor of the enzyme thermolysin, a membrane metallo-endopeptidase inhibitor, and an endothelin converting enzyme inhibitor.

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.

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

InChI:InChI=1/C23H34N3O10P.Na/c1-11(2)8-16(26-37(33,34)36-23-20(29)19(28)18(27)12(3)35-23)21(30)25-17(22(31)32)9-13-10-24-15-7-5-4-6-14(13)15;/h4-7,10-12,16-20,23-24,27-29H,8-9H2,1-3H3,(H,25,30)(H,31,32)(H2,26,33,34);