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
References
[1] PAUL A. WENDER. Oligocarbamate Molecular Transporters: Design, Synthesis, and Biological Evaluation of a New Class of Transporters for Drug Delivery[J]. Journal of the American Chemical Society, 2002, 124 45: 13382-13383. DOI:
10.1021/ja0275109[2] AJAY KUMAR . Enhanced gene transfection efficiency by polyamidoamine (PAMAM) dendrimers modified with ornithine residues[J]. International Journal of Pharmaceutics, 2010, 392 1: Pages 294-303. DOI:
10.1016/j.ijpharm.2010.03.054
