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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

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0.5 mg

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1 mg

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5 mg

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10 mg
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25 mg
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About This Item

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

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Product Name

Phosphoramidon disodium salt, ≥97% (HPLC)

biological source

Streptomyces sp.

Quality Segment

assay

≥97% (HPLC)

form

powder

input

general use sample(s)

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.

Compare Similar Items

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Show Differences

1 of 1

This Item
N7255525276670107
description

≥97% (HPLC)

description

phosphatase substrate

description

Inhibits some metalloendopeptidases.

description

Donor substrate for N-acetylglucosaminyltransferases. Useful in the synthesis of aryl azide derivatives that can be used in the affinity labeling of glycosyltransferase and UDP-HexNAc pyrophosphorylase.

biological source

Streptomyces sp.

biological source

-

biological source

-

biological source

-

assay

≥97% (HPLC)

assay

-

assay

-

assay

≥95% (HPLC)

Quality Level

200

Quality Level

200

Quality Level

100

Quality Level

100

form

powder

form

powder

form

lyophilized solid

form

crystalline powder

storage temp.

−20°C

storage temp.

−20°C

storage temp.

2-8°C

storage temp.

−20°C

solubility

H2O: 50 mg/mL

solubility

water: 50 mg/mL, clear, colorless to very faintly yellow

solubility

DMSO: 10 mg/mL, methanol: soluble, water: soluble

solubility

water: 50 mg/mL


Storage Class

11 - Combustible Solids

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)



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