36357-77-4

Basic information

• Product Name: PHOSPHORAMIDON
• Synonyms: eucyl)-;l-tryptophan,n-(n-(((6-deoxy-alpha-l-mannopyranosyl)oxy)hydroxyphosphinyl)-l-l;n-(n-(((6-deoxy-alpha-l-mannopyranosyl)oxy)hydroxyphosphinyl)-l-leucyl)-l-tr;yptophan;PHOSPHORAMIDON;PHOSPHORAMIDON DISODIUM SALT DIHYDRATE;PHOSPHORAMIDON SODIUM SALT;N-(A-RHAMNOPYRANOSYLOXYHYDROXYPHOSPHINYL)-LEU-TRP
• CAS NO: 36357-77-4
• Molecular Formula: C₂₃H₃₄N₃O₁₀P
• Molecular Weight: 543.5
• EINECS: 252-996-3
• Product Categories: Pepetides;peptides
• Mol File: 36357-77-4.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• Density: 1.48 g/cm³
• Storage Temp.: −20°C
• Solubility: H2O: 1 mM Stock solution stable for 1 month at –20&#
• PKA: -0.66±0.50(Predicted)
• CAS DataBase Reference: PHOSPHORAMIDON(CAS DataBase Reference)
• NIST Chemistry Reference: PHOSPHORAMIDON(36357-77-4)
• EPA Substance Registry System: PHOSPHORAMIDON(36357-77-4)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• F: 10-21
• Hazardous Substances Data: 36357-77-4(Hazardous Substances Data)

Usage

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.

Upstream product

• 56361-75-2 N-Phospho-L-leucyl-L-tryptophan 
• 2147-59-3 thymidine 5'-diphospho-β-L-rhamnose 

Downstream Products

• 7658-10-8 6-Deoxy-L-talose 
• 5156-22-9 L-leucyl-L-tryptophan 

Relevant articles and documents

Biosynthetic reconstitution of deoxysugar phosphoramidate metalloprotease inhibitors using an N-P-bond-forming kinase

Phosphoramidon is a potent metalloprotease inhibitor and a widespread tool in cell biology research. It contains a dipeptide backbone that is uniquely linked to a 6-deoxysugar via a phosphoramidate bridge. Herein, we report the identification of a gene cluster for the formation of phosphoramidon and its detailed characterization. In vitro reconstitution of the biosynthesis established TalE as a phosphoramidate-forming kinase and TalC as the glycosyltransferase which installs the l-rhamnose moiety by phosphoester linkage.