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Phosphoramidon

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Not to be confused with phosphamidon.
Phosphoramidon
Skeletal formula of phosphoramidon
Space-filling model of the phosphoramidon molecule
Names
IUPAC name (2S)-2-oxyphosphoryl]amino]-4-methylpentanoyl]amino]-3-(1H-indol-3-yl)propanoic acid
Other names N-hydroxyphosphinyl]-L-leucyl]-L-tryptophan
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.048.164 Edit this at Wikidata
EC Number
  • 252-996-3
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C23H34N3O10P/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)/t12-,16-,17-,18-,19+,20+,23-/m0/s1Key: ZPHBZEQOLSRPAK-XLCYBJAPSA-N
  • InChI=1/C23H34N3O10P/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)/t12-,16-,17-,18-,19+,20+,23-/m0/s1Key: ZPHBZEQOLSRPAK-XLCYBJAPBL
SMILES
  • O=C(O)(NC((CC(C)C)NP(O1O(C)(O)(O)1O)(O)=O)=O)CC2=CNC3=C2C=CC=C3
Properties
Chemical formula C23H34N3O10P
Molar mass 543.510 g·mol
Appearance White to slightly yellow solid
Solubility in water Soluble as sodium salt
Solubility in DMSO and methanol Soluble as sodium salt
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Phosphoramidon is a chemical compound derived from cultures of Streptomyces tanashiensis. It is an inhibitor of the enzyme thermolysin, of the membrane metallo-endopeptidase, and of the endothelin converting enzyme. Chemically, phosphoramidon differs from its closely related peptidase inhibitor talopeptin by a single stereocenter.

Because of its enzyme inhibitory properties, phosphoramidon is widely used as a biochemical tool.

References

  1. ^ Phosphoramidon, Enzo Life Sciences
  2. Kitagishi K, Hiromi K (1984). "Binding between thermolysin and its specific inhibitor, phosphoramidon". Journal of Biochemistry. 95 (2): 529–34. PMID 6715312.
  3. ^ Phosphoramidon at PubChem

External links

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