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R7385 Sigma-Aldrich

Phosphoramidon disodium salt

≥97% (HPLC)

Synonym: N-(α-Rhamno­pyranosyl­oxy­hydroxy­phosphinyl)-Leu-Trp disodium salt, N-(α-Rhamno­pyranosyl­phos­phono)-L-leucyl-L-tryptophan disodium salt

  • CAS Number 119942-99-3

  • Empirical Formula (Hill Notation) C23H32N3Na2O10P

  • Molecular Weight 587.47

  •  Beilstein/REAXYS Number 8105669

  •  MDL number MFCD00077870

  •  PubChem Substance ID 24278681

  •  NACRES NA.77

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Properties

Related Categories Biochemicals and Reagents, Broad Spectrum Inhibitors of Proteolytic Enzyme Classes, Core Bioreagents, Enzyme Inhibitors, Enzyme Inhibitors by Enzyme,
Quality Level   200
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. Phosphoramidate is produced naturally by Streptomyces tanashiensis.

Application

Phosphoramidon disodium salt has been used:
• as the neprilysin (NEP) inhibitor: in amyloid beta (Aβ) uptake and degradation
• to study its effect on keratinase activity
• to treat primary microglia from wild-type mice

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.

Packaging

0.5, 1, 5 mg in glass bottle

10, 25 mg in poly bottle

Biochem/physiol Actions

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

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.

Features and Benefits

This compound is also offered as part of Sigma′s Library of Pharmacologically Active Compounds (LOPAC®1280), a biologically annotated collection of high-quality, ready-to-screen compounds. Click here to learn more.

Legal Information

LOPAC is a registered trademark of Sigma-Aldrich Co. LLC

Safety & Documentation

Safety Information

Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles
Peer-Reviewed Papers
15

References

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