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R7385

Sigma-Aldrich

Phosphoramidon disodium salt

powder, ≥97% (HPLC)

Synonym(s):

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

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0.5 MG
$73.35
1 MG
$149.00
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$307.28
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$557.60
25 MG
$1,122.00

$73.35

List Price$86.30Save 15%

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0.5 MG
$73.35
1 MG
$149.00
5 MG
$307.28
10 MG
$557.60
25 MG
$1,122.00

About This Item

Empirical Formula (Hill Notation):
C23H32N3Na2O10P
CAS Number:
119942-99-3
Molecular Weight:
587.47
Beilstein/REAXYS Number:
8105669
MDL number:
MFCD00077870
UNSPSC Code:
12352202
PubChem Substance ID:
24278681
NACRES:
NA.77

$73.35

List Price$86.30Save 15%

In StockDetails

Product Name

Phosphoramidon disodium salt, ≥97% (HPLC)

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.[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.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
0000375068
0000369853
0000369853
0000316588
0000375068

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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
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)
Christoph Nicolaus et al.
Journal of ethnopharmacology, 196, 94-103 (2016-12-14)
Calendula officinalis (pot marigold) flower extracts have a long-lasting tradition in ethnopharmacology. Currently, the European Medicines Agency (EMA) has approved its lipophilic and aqueous alcoholic extracts as traditional medicinal products for the treatment of minor inflammation of the skin and
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)
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