Phosphoramidon

Phosphoramidon
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
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 [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

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.

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