2667-02-9

Basic information

• Product Name: PHE-PHE-PHE-PHE ACETATE SALT
• Synonyms: PHE-PHE-PHE-PHE ACETATE SALT;TETRA-L-PHENYLALANINE ACETATE SALT;phe-phe-phe-phe acetate;Tetra-L-phenylalanine
• CAS NO: 2667-02-9
• Molecular Formula: C₃₆H₃₈N₄O₅
• Molecular Weight: 666.76
• Mol File: 2667-02-9.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• Storage Temp.: −20°C
• CAS DataBase Reference: PHE-PHE-PHE-PHE ACETATE SALT(CAS DataBase Reference)
• NIST Chemistry Reference: PHE-PHE-PHE-PHE ACETATE SALT(2667-02-9)
• EPA Substance Registry System: PHE-PHE-PHE-PHE ACETATE SALT(2667-02-9)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 2667-02-9(Hazardous Substances Data)

Upstream product

• 5241-58-7 L-Phenylalanine amide 
• 302-72-7 rac-Ala-OH 
• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 962-39-0 L-Phenylalanine benzyl ester 
• 70669-39-5 Phe-Phe-OBzl 
• 66617-58-1 N-(tert-butoxycarbonyl)-L-phenylalanine benzyl ester 
• 16879-80-4 tert-butyl ((S)-1-oxo-1-(((S)-3-oxo-1,4-diphenylbutan-2-yl)amino)-3-phenylpropan-2-yl)carbamate 
• 69700-83-0 Boc-L-Phe-L-Phe-L-Phe-OBzl 
• 35661-40-6 N-Fmoc L-Phe 

Relevant articles and documents

Bioconjugates of Co(III) complexes with Schiff base ligands and cell penetrating peptides: Solid phase synthesis, characterization and antiproliferative activity

In this work we synthesized a chelating Schiff base by a single condensation of salicylaldehyde with 3,4-diamino benzoic acid (1). This ligand was used further for complexation to CoCl2·6H2O under nitrogen. In the next step, three six-coordinate Co(III) complexes were synthesized by coordinating this complex with imidazole (2), 2-methyimidazole (3) and N-Boc-L-histidine methyl ester (4) (Boc: tert.-butoxycarbonyl) in axial positions with simultaneous oxidation of Co(II) to Co(III) under ambient environment. All Co(III) complexes were characterized by multinuclear NMR spectroscopy (1H, 13C and 59Co NMR), FT-IR, mass spectrometry and HPLC. The Co(III) complexes were conjugated to three different cell penetrating peptides: FFFF (P1), RRRRRRRRRGAL (P2) and FFFFRRRRRRRRRGAL (P3). Standard solid-phase peptide chemistry was used for the synthesis of cell penetrating peptides. Coupling of N-terminal peptides with the cobalt complexes, possessing a carboxylic group on the tetradentate Schiff base ligand, afforded Co(III)-peptide bioconjugates, which were purified by semi-preparative HPLC and characterized by analytical HPLC and mass spectrometry. The antiproliferative activity of the synthesized compounds was studied against different human tumour cell lines: lung cancer A549, liver cancer HepG2 and normal human fibroblasts GM5657T, in comparison with the activity of cisplatin as a reference drug. The bioconjugate 21 containing the Co complex 4 and the combined phenylalanine and polyarginine cell penetrating sequence P3 shows better activity against the liver cancer line HepG2 than the parent Co(III) complex 4.

Biomimetic peptide bond formation in water with aminoacyl phosphate esters

Aminoacyl phosphates, biomimetic analogues of aminoacyl adenylates, react efficiently with amino acid esters to form dipeptides with retention of stereochemical integrity. The reactions are selective and occur readily in the presence of nucleophiles other than amino groups on their side chains. Aminoacyl phosphate esters that lack an amino-protecting group are also suitable for peptide bond formation, leading to a simplified overall process.

Biomimetic protecting-group-free 2′, 3′-selective aminoacylation of nucleosides and nucleotides

Aminoacyl phosphate monoesters can be prepared free of an amino-protecting group and used directly in lanthanum-promoted selective monoacylation of either the 2′ or 3′-hydroxyl of nucleosides and nucleotides. For example, phenylalanyl ethyl phosphate rapi