| Identification | Back Directory | [Name]
PHOSPHORAMIDON | [CAS]
36357-77-4 | [Synonyms]
eucyl)-
yptophan
PHOSPHORAMIDON
PHOSPHORAMIDON SODIUM SALT
PHOSPHORAMIDON DISODIUM SALT DIHYDRATE
N-(A-RHAMNOPYRANOSYLOXYHYDROXYPHOSPHINYL)-LEU-TRP
N-(ALPHA-RHAMNOPYRANOSYLOXYHYDROXYPHOSPHINYL)-LEU-TRP-OH
N-(ALPHA-RHAMNOPYRANOSYLOXYHYDROXYPHOSPHINYL)-LEU-TRP 2NA
N-(ALPHA-RHAMNOPYRANOSYLOXYHYDROXYPHOSPHINYL)-LEU-TRP SODIUM SALT
N-(ALPHA-RHAMNOPYRANOSYLOXYHYDROXYPHOSPHINYL)-L-LEUCYL-L-TRYPTOPHAN
N-(ALPHA-RHAMNOPYRANOSYLPHOSPHONO)-L-LEUCYL-L-TRYPTOPHAN DISODIUM SALT
N-[N-[(6-Deoxy-α-L-mannopyranosyloxy)hydroxyphosphinyl]-L-Leu-]-L-Trp-OH
N-(ALPHA-RHAMNOPYRANOSYLOXYHYDROXYPHOSPHINYL)-L-LEUCYL-L-TRYPTOPHAN, 2NA
n-(n-(((6-deoxy-alpha-l-mannopyranosyl)oxy)hydroxyphosphinyl)-l-leucyl)-l-tr
L-Tryptophan,N-[[(6-deoxy-a-L-mannopyranosyl)oxy]hydroxyphosphinyl]-L-leucyl-
l-tryptophan,n-(n-(((6-deoxy-alpha-l-mannopyranosyl)oxy)hydroxyphosphinyl)-l-l
L-Tryptophan, N-[[(6-deoxy-α-L-mannopyranosyl)oxy]hydroxyphosphinyl]-L-leucyl-
N-(ALPHA-RHAMNOPYRANOSYLOXYHYDROXYPHOSPHINYL)-L-LEUCYL-L-TRYPTOPHAN (SODIUM SALT)
N-(ALPHA-RHAMNOPYRANOSYLOXYHYDROXY-PHOSPHINYL)-L-LEUCYL-L-TRYPTOPHAN DISODIUM SALT
N-[N-[[(6-deoxy-alpha-L-mannopyranosyl)oxy]hydroxyphosphinyl]-L-leucyl]-L-tryptophan
N-(ALPHA-RHAMNOPYRANOSYLOXYHYDROXYPHOSPHINYL)-L-LEUCYL-L-TRYPTOPHAN DISODIUM SALT DIHYDRATE | [EINECS(EC#)]
252-996-3 | [Molecular Formula]
C23H34N3O10P | [MDL Number]
MFCD00080262 | [MOL File]
36357-77-4.mol | [Molecular Weight]
543.51 |
| Chemical Properties | Back Directory | [density ]
1.48±0.1 g/cm3(Predicted) | [storage temp. ]
−20°C | [solubility ]
H2O: 1 mM Stock solution stable for 1 month at –20° C. | [pka]
-0.66±0.50(Predicted) |
| Hazard Information | Back Directory | [Uses]
Phosphoramidon, a microbial metabolite, is a specific metalloprotease thermolysin inhibitor with an IC50 of 0.4 μg/mL. Phosphoramidon also inhibits endothelin-converting enzyme (ECE), neutral endopeptidase (NEP), and angiotensin-converting enzyme (ACE) with IC50 values of 3.5, 0.034, and 78 μM, respectively[1][2][3]. | [Definition]
ChEBI: A dipeptide isolated from the cultures of Streptomyces tanashiensis. | [Enzyme inhibitor]
This glycosyl phosphoramidopeptide (FWfree-acid = 543.51 g/mol; CAS 36357-77-4), also systematically named as N-(a-rhamnopyranosyloxyhydroxyphosphinyl)- L-leucyl-L-tryptophan, is a slow-binding thermolysin inhibitor (Ki = 30 nM). Note: Phosphoramidon is an epimer of talopeptin. Stock 1 mg/mL aqueous solutions of phosphoramidon are stable for one month at –20°C. Target(s): atrolysin A; atrolysin C; bacillolysin; carboxypeptidase C, weakly inhibited; coccolysin; cytosol alanyl aminopeptidase, weakly inhibited; dactylysin; endothelin-converting enzyme; endothelin-converting enzyme 2; fungalysin; gametolysin; granzyme B; Legionella metalloendopeptidase; leucyl aminopeptidase, weakly inhibited; Listeria metalloprotease Mpl; lysine carboxypeptidase, or lysine(arginine) carboxypeptidase; carboxypeptidase N; mycolysin; neprilysin, or enkephalinase, Ki = 0.8 nM; oligopeptidase O; peptidyl-dipeptidase A, or angiotensin I-converting enzyme; pitrilysin, or protease Pi; pseudolysin, or Pseudomonas aeruginosa elastase; pyruvate decarboxylase; thermolysin (27,28,41,43- 53); urethanase; vibriolysin; and Xaa-Pro aminopeptidase, or aminopeptidase P. | [in vivo]
Phosphoramidon (0.25 mg/kg per min; i.v.) suppresses the hypertensive effect of big endothelin-1 in rats[4].
Phosphoramidon (1-30 mg/kg; i.v.; once) blocks the pressor activity of porcine big endothelin-1-(1-39) in rats[5]. | Animal Model: | Male Sprague-Dawley rats[4] | | Dosage: | 0.25 mg/kg per min | | Administration: | Intravenous injection | | Result: | Markedly suppressed the hypertensive effect of big endothelin-1. |
| [IC 50]
Microbial Metabolite | [References]
[1] Umezawa S, , et al. A new microbial metabolite phosphoramidon (isolation and structure). Tetrahedron Letters, 1972, 13(1): 97-100.
[2] Suda H, et al. A thermolysin inhibitor produced by actinomycetes: phosphoramidon. The Journal of antibiotics, 1973, 26(10): 621-623.
[3] Kukkola PJ, et al. Differential structure-activity relationships of phosphoramidon analogues for inhibition of three metalloproteases: endothelin-converting enzyme, neutral endopeptidase, and angiotensin-converting enzyme.J CardiovascPharmacol. 1995;26Suppl 3:S65-8. PMID:8587470
[4] Matsumura Y, et al. Phosphoramidon, a metalloproteinase inhibitor, suppresses the hypertensive effect of big endothelin-1. Eur J Pharmacol. 1990 Aug 21;185(1):103-6. DOI:10.1016/0014-2999(90)90216-s
[5] McMahon EG, et al. Phosphoramidon blocks the pressor activity of porcine big endothelin-1-(1-39) in vivo and conversion of big endothelin-1-(1-39) to endothelin-1-(1-21) in vitro. Proc Natl Acad Sci U S A. 1991 Feb 1;88(3):703-7. DOI:10.1073/pnas.88.3.703 |
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