Description
Fmoc-Pro-OH is easily dissolved in DMF or NMP. Proline fails to produce a blue-to purple color in the Kaiser test. The Isatin test may be used to test the completion of couplings to proline residues.
Chemical Properties
white to light yellow crystal powder.
Uses
L-Proline-N-Fmoc is N-Fmoc protected L-Proline (P755995) which is an amino acid and precursor (with vitamin C) for collagen, the building block of the structure of tendons, ligaments, arteries, veins and muscles. It is important in wound healing.
Preparation
To a solution of (S)-pyrrolidine-2-carboxylic acid (1 g, 8.7 mmol) in 1,4-dioxane (4 mL) and water (15 mL), K2CO3 (3.24 g, 23 mmol) was added, followed by the addition of 9-fluorenylmethyl chloroformate (2.3 g, 8.3 mmol). The resulting mixture was stirred overnight at room temperature and then treated with water (10 mL). The resulting mixture was extracted with diethyl ether (2 x 20 mL), and the aqueous phase was made acidic with 1M HCl to a pH of 2-3, followed by extraction with dichloromethane (3 x 50 mL). The combined organic layers were dried using anhydrous sodium sulfate and concentrated to yield Fmoc-Pro-OH as a white solid in a 95% yield (2.8 g).
General Description
Fmoc-Pro-OH has been instrumental in synthesizing peptides and proteins and in the development of new agents. Additionally, Fmoc-P-OH has been extensively employed in both in vivo and in vitro studies, with a focus on enzyme function, protein structure, and drug design investigations.
reaction suitability
reaction type: Fmoc solid-phase peptide synthesis
