phosphoramidon

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/10/22 16:57:47」(JST)

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Not to be confused with phosphamidon.

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 Y
ChEBI	CHEBI:45353 N
ChEMBL	ChEMBL479579 N
ChemSpider	392848 N
ECHA InfoCard	100.048.164
EC Number	252-996-3
Jmol 3D model	Interactive image
KEGG	C00563 N
PubChem	445114
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 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
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	543.51 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).
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, a membrane metallo-endopeptidase inhibitor, and an endothelin converting enzyme inhibitor. 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

External links

• The MEROPS online database for peptidases and their inhibitors: Phosphoramidon

UpToDate Contents

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• 1. 心不全におけるエンドセリンの役割 role of endothelin in heart failure

English Journal

• Structure of Gentlyase, the neutral metalloprotease of Paenibacillus polymyxa.

• Ruf A, Stihle M, Benz J, Schmidt M, Sobek H.SourcepRED Pharma Research and Early Development, Small Molecule Research, Discovery Technologies, F. Hoffmann-La Roche Ltd, CH-4070 Basel, Switzerland.
• Acta crystallographica. Section D, Biological crystallography.Acta Crystallogr D Biol Crystallogr.2013 Jan;69(Pt 1):24-31. doi: 10.1107/S0907444912041169. Epub 2012 Dec 20.
• Gentlyase is a bacterial extracellular metalloprotease that is widely applied in cell culture and for tissue dissociation and that belongs to the family of thermolysin-like proteases. The structure of thermolysin has been known since 1972 and that of Bacillus cereus neutral protease since 1992. Howe
• PMID 23275160

• Dynamic changes in the secondary structure of ECE-1 and XCE account for their different substrate specificities.

• Ul-Haq Z, Iqbal S, Moin ST.AbstractABSTRACT: BACKGROUND: X-converting enzyme (XCE) involved in nervous control of respiration, is a member of the M13 family of zinc peptidases, for which no natural substrate has been identified yet. In contrast, it's well characterized homologue endothelin-converting enzyme-1 (ECE-1) showed broad substrate specificity and acts as endopeptidase as well as dipeptidase. To explore the structural differences between XCE and ECE-1, homology model of XCE was built using the complex structure of ECE-1 with phosphoramidon (pdb-id: 3DWB) as template. Phosphoramidon was docked into the binding site of XCE whereas phosphate oxygen of the inhibitor was used as water molecule to design the apo forms of both enzymes. Molecular dynamics simulation of both enzymes was performed to analyze the dynamic nature of their active site residues in the absence and presence of the inhibitor.
• BMC bioinformatics.BMC Bioinformatics.2012 Nov 1;13(1):285. [Epub ahead of print]
• ABSTRACT: BACKGROUND: X-converting enzyme (XCE) involved in nervous control of respiration, is a member of the M13 family of zinc peptidases, for which no natural substrate has been identified yet. In contrast, it's well characterized homologue endothelin-converting enzyme-1 (ECE-1) showed broad sub
• PMID 23113990

• Neurogenic airway microvascular leakage induced by toluene inhalation in rats.

• Sakamoto T, Kamijima M, Miyake M.SourceDepartment of Hygiene, Yamaguchi University Graduate School of Medicine, Kogushi 1-1-1, Ube 755-8505, Japan. sakamoto@yamaguchi-u.ac.jp
• European journal of pharmacology.Eur J Pharmacol.2012 Jun 15;685(1-3):180-5. doi: 10.1016/j.ejphar.2012.04.035. Epub 2012 Apr 24.
• Toluene is a representative airborne occupational and domestic pollutant that causes eye and respiratory tract irritation. We investigated whether a single inhalation of toluene elicits microvascular leakage in the rat airway. We also evaluated the effects of CP-99,994, a tachykinin NK(1) receptor a
• PMID 22554773

Japanese Journal

• Purification and characterization of an eggshell membrane decomposing protease from Pseudomonas aeruginosa strain ME-4(ENZYMOLOGY, PROTEIN ENGINEERING, AND ENZYME TECHNOLOGY)

• Cheng Minyi,Takenaka Shinji,Aoki Shunsuke,Murakami Shuichiro,Aoki Kenji
• Journal of bioscience and bioengineering 107(4), 373-378, 2009-04
• … The isolated enzyme was a metalloprotease and was strongly inhibited by EDTA, o-phenanthroline, and phosphoramidon. …
• NAID 110007225812

• Great Increase in Antinociceptive Potency of [Leu^5]Enkephalin After Peptidase Inhibition

• AKAHORI Kazuhito,KOSAKA Kenya,JIN Xing Lu,ARAI Yoshiharu,YOSHIKAWA Masanobu,KOBAYASHI Hiroyuki,OKA Tetsuo
• Journal of pharmacological sciences 106(2), 295-300, 2008-02-20
• … Previous in vitro studies have shown that the degradation of [Leu5]enkephalin during incubation with cerebral membrane preparations is almost completely prevented by a mixture of three peptidase inhibitors: amastatin, captopril, and phosphoramidon. …
• NAID 10024318545

Related Links

• Phosphoramidon - Wikipedia, the free encyclopedia

Phosphoramidon. 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 ...

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