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R7385

Sigma-Aldrich

Phosphoramidon disodium salt

≥97% (HPLC)

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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

biological source

Streptomyces sp.

Quality Level

200

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

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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.

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.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Thermolysin and Related Bacillus Metallopeptidases
Handbook of Proteolytic Enzymes, 1, 540-553 (2013)
Phosphoramidon inhibits the integral membrane protein zinc metalloprotease ZMPSTE24
Goblirsch BR, et al.
Acta crystallographica. Section D, Structural biology, 74(Pt 8), 739-739 (2018)
Deacetylation of TFEB promotes fibrillar A beta degradation by upregulating lysosomal biogenesis in microglia
Bao J, et al.
Protein & cell, 7(6), 417-433 (2016)
J R Wu-Wong et al.
Molecular pharmacology, 44(2), 422-429 (1993-08-01)
Endothelin (ET) is generated from prepro-ET by dibasic pair proteolysis, followed by specific proteolytic cleavage between Trp21 and Val22. Currently, intense research efforts are focused on the investigation of a metalloprotease-like ET-converting enzyme that is inhibited by phosphoramidon but not
SIRT1 facilitates amyloid beta peptide degradation by upregulating lysosome number in primary astrocytes
Li MZ, et al.
Neural Regeneration Research, 13(11), 2005-2005 (2018)
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