Key Documents

View All Documentation

R7385

Phosphoramidon disodium salt

Name: Phosphoramidon disodium salt
Brand: SIGMA

powder, ≥97% (HPLC)

Synonym(s):

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

Select a Size

Change View

About This Item

Empirical Formula (Hill Notation):

C₂₃H₃₂N₃Na₂O₁₀P

CAS Number:

119942-99-3

Molecular Weight:

587.47

NACRES:

NA.77

PubChem Substance ID:

24278681

UNSPSC Code:

12352202

MDL number:

MFCD00077870

Beilstein/REAXYS Number:

8105669

Technical Service

Need help? Our team of experienced scientists is here for you.

Let Us Assist

Product Name

Phosphoramidon disodium salt, ≥97% (HPLC)

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

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.

Storage Class

11 - Combustible Solids

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number

0000526516

WXBF6432V

720409

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

The relationships between enzyme inhibitors and function of mammalian cells.

T Aoyagi et al.

Acta biologica et medica Germanica, 40(10-11), 1523-1529 (1981-01-01)

We have been searching for enzyme inhibitors in culture filtrates of microbes and have found leupeptin, antipain, chymostatin, elastatinal, pepstatin, hydroxypepstatin, pepstanone and phosphoramidon as specific inhibitors of serine, thiol, carboxyl and metallo proteases. We found significant activities of aminopeptidases

Thermolysin and Related Bacillus Metallopeptidases

Handbook of Proteolytic Enzymes, 1, 540-553 (2013)

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)

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)

Smart cleaning properties of a multi tolerance keratinolytic protease from an extremophilic Bacillus tequilensis hsTKB2: prediction of enzyme modification site

Paul T, et al.

Waste and biomass valorization, 5(6), 931-945 (2014)

View All Related Papers

Global Trade Item Number

SKU	GTIN
R7385-10MG	04061833274057
R7385-.5MG	04061833274040
R7385-1MG	04061826676806
R7385-25MG	04061833274064
R7385-5MG	04061833274071

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service