R7385

Phosphoramidon disodium salt

powder, ≥97% (HPLC)

• Synonym(s): N-(α-Rhamno­pyranosyl­oxy­hydroxy­phosphinyl)-Leu-Trp disodium salt, N-(α-Rhamno­pyranosyl­phos­phono)-L-leucyl-L-tryptophan disodium salt
• Empirical Formula (Hill Notation): C₂₃H₃₂N₃Na₂O₁₀P
• CAS Number: 119942-99-3
• Molecular Weight: 587.47
• Beilstein: 8105669
• MDL number: MFCD00077870
• UNSPSC Code: 12352202
• PubChem Substance ID: 24278681
• NACRES: NA.77

Properties

• Product Name: Phosphoramidon disodium salt, ≥97% (HPLC)
• biological source: Streptomyces sp.
• Assay: ≥97% (HPLC)
• form: powder
• solubility: H₂O: 50 mg/mL
• storage temp.: −20°C
• SMILES string: [Na+].[Na+].CC(C)C[C@H](NP([O-])(=O)O[C@@H]1O[C@@H](C)[C@H](O)[C@@H](O)[C@H]1O)C(=O)N[C@@H](Cc2c[nH]c3ccccc23)C([O-])=O
• InChI: 1S/C23H34N3O10P.2Na/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);;/q;2*+1/p-2/t12-,16-,17-,18-,19+,20+,23-;;/m0../s1
• InChI key: OQKHVXFOYFBMDJ-ODIUWQMJSA-L

Description

General description

Phosphoramidon [N-(α-rhamnopyranosyl-oxyhydroxyphosphinyl)-Leu-Trp] is a competitive inhibitor of several soluble zinc metalloproteases.[1] Phosphoramidate is produced naturally by Streptomyces tanashiensis.[2]

Application

Identification of phosphoramidon as a metallo-endopeptidase inhibitor was used to characterize endothelin converting enzyme as a metallo-endopeptidase. Phosphoramidon increases the production of β-amyloid protein, but not amyloid precursor protein, indicating that abnormal amyloid processing in Alzheimer′s disease may be carried out by a metallo-endopeptidase.

Phosphoramidon disodium salt has been used:

• as the neprilysin (NEP) inhibitor: in amyloid beta (Aβ) uptake and degradation[3]
• to study its effect on keratinase activity[4]
• to treat primary microglia from wild-type mice[5]

Biochem/physiol Actions

Phosphoramidon can inhibit ZMPSTE24, an integral membrane protein zinc metalloprotease.[1] It is capable of blocking thermolysin.[2]

Phosphoramidon is a potent inhibitor of thermolysin and other metallo-endopeptidases. It trongly inhibits mammalian enkephalinase and it does not inhibit trypsin, papain, chymotrypsin or pepsin. It weakly inhibits collagenase.

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves