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
CAS Number	36357-77-4 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:45353 ;
ChEMBL	ChEMBL479579 ;
ChemSpider	392848 ;
ECHA InfoCard	100.048.164
EC Number	252-996-3;
KEGG	C00563 ;
PubChem CID	445114;
UNII	T3G94E2LB1 ;
CompTox Dashboard (EPA)	DTXSID601317292 ;
	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/s1 Key: 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/s1 Key: ZPHBZEQOLSRPAK-XLCYBJAPBL;
	SMILES 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
Chemical formula	C23H34N3O10P
Molar mass	543.510 g·mol−1
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 [77 °F], 100 kPa). verify (what is ?) Infobox references

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]^[4] 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

^ ^a ^b Phosphoramidon, Enzo Life Sciences
^ Kitagishi K, Hiromi K (1984). "Binding between thermolysin and its specific inhibitor, phosphoramidon". Journal of Biochemistry. 95 (2): 529–34. doi:10.1093/oxfordjournals.jbchem.a134635. PMID 6715312.
^ ^a ^b Phosphoramidon at PubChem
^ Schulz, Henk; Dale, Glenn E.; Karimi-Nejad, Yasmin; Oefner, Christian (2009-01-09). "Structure of human Endothelin-converting Enzyme I Complexed with Phosphoramidon". Journal of Molecular Biology. 385 (1): 178–187. doi:10.1016/j.jmb.2008.10.052. ISSN 0022-2836.

External links

The MEROPS online database for peptidases and their inhibitors: Phosphoramidon

[Enzo-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. doi:10.1093/oxfordjournals.jbchem.a134635. PMID 6715312.

[PubChem-3] Phosphoramidon at PubChem

[4] Schulz, Henk; Dale, Glenn E.; Karimi-Nejad, Yasmin; Oefner, Christian (2009-01-09). "Structure of human Endothelin-converting Enzyme I Complexed with Phosphoramidon". Journal of Molecular Biology. 385 (1): 178–187. doi:10.1016/j.jmb.2008.10.052. ISSN 0022-2836.

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