Fmoc-Orn(Boc)-OH

Description

Fmoc-Orn(Boc)-OH is an ornithine-containing amino acid building block. It has been used to conjugate ornithine to GFP-labeled peptides, enhancing cell permeability when compared to unconjugated GFP-labeled peptides. This compound is useful in preparing cyclic peptides and special arginine derivates.

Chemical Properties

White powder

Uses

Fmoc-Orn(Boc)-OH is a biochemical reagent. It can be used as a biomaterial or organic compound in life science-related research.

Preparation

2 mmol L-Orn was weighted and dissolved in 15 ml of acetonitrile; 16 mmol Boc2O was dissolved in acetonitrile and added dropwise to an acetonitrile solution of ornithine, to react and generate a complex; 10 ml 20% sodium bicarbonate aqueous solution was added, and 2 g of anhydrous sodium carbonate and an appropriate amount of 8-hydroxyquinoline were added in batches; the mixture was stirred and reacted at room temperature for 4 hours to remove copper ions in the complex; then 2 mmol Fmoc-OSu was added to the aforesaid solution, followed by stirring at room temperature for 2 hours; the resultant was recrystallized with an ethyl acetate/petroleum ether mixed solvent, to obtain a peptide head intermediate Fmoc-Orn(Boc)-OH.

reaction suitability

Reaction type: Fmoc solid-phase peptide synthesis

Solubility in organics

DMF: 20 mg/ml, DMF:PBS (pH 7.2) (1:5): 0.16 mg/ml, DMSO: 10 mg/ml, Ethanol: 10 mg/ml