Phosphoramidon

Phosphoramidon is a chemical compound derived from cultures of Streptomyces tanashiensis. It is an inhibitor of the enzyme thermolysin,[2] of the membrane metallo-endopeptidase,[3] and of the endothelin converting enzyme.[3] Chemically, phosphoramidon differs from its closely related peptidase inhibitor talopeptin by a single stereocenter.

Not to be confused with phosphamidon.
Phosphoramidon
Skeletal formula of phosphoramidon
Space-filling model of the phosphoramidon molecule
Names
IUPAC name
(2S)-2-[[(2S)-2-[[hydroxy-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyphosphoryl]amino]-4-methylpentanoyl]amino]-3-(1H-indol-3-yl)propanoic acid
Other names
N-[N-[[(6-deoxy-α-L-mannoopyranosyl)oxy]hydroxyphosphinyl]-L-leucyl]-L-tryptophan
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.048.164
EC Number
  • 252-996-3
KEGG
UNII
  • 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/s1 ☒N
    Key: ZPHBZEQOLSRPAK-XLCYBJAPSA-N ☒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/s1
    Key: ZPHBZEQOLSRPAK-XLCYBJAPBL
  • O=C(O)[C@@H](NC([C@H](CC(C)C)NP(O[C@@H]1O[C@@H](C)[C@H](O)[C@@H](O)[C@H]1O)(O)=O)=O)CC2=CNC3=C2C=CC=C3
Properties
C23H34N3O10P
Molar mass 543.510 g·mol−1
Appearance White to slightly yellow solid
Soluble as sodium salt[1]
Solubility in DMSO and methanol Soluble as sodium salt[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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
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