Description
Fmoc-12-aminododecanoic acid is an alkane chian with terminal Fmoc-protected amine and carboxylic acid groups. The compound can be used as a PROTAC linker in the synthesis of PROTACs. The Fmoc group can be deprotected under basic condition to obtain the free amine which can be used for further conjugations. The terminal carboxylic acid can react with primary amine groups in the presence of activators (e.g. EDC, or HATU) to form a stable amide bond.
Chemical Properties
White to off-white powder
Uses
12-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)dodecanoic Acid has been used as a reactant for the preparation of pro-apoptotic peptide functionalized gold nanoparticles as a new anti-cancer strategy of damaging mitochondria.
reaction suitability
reaction type: Fmoc solid-phase peptide synthesis
Synthesis
GENERAL STEPS: 9-Fluorenylmethyl-N-succinimidyl carbonate (Fmoc-OSu, 6.55 g, 21.9 mmol) and sodium bicarbonate (NaHCO3, 2.39 g, 28.5 mmol) were added to a mixture of acetone (90 mL) and water (90 mL) of 12-aminodododecanoic acid (4.71 g, 21.9 mmol). The reaction mixture was stirred at room temperature for 20 hours. Upon completion of the reaction, the pH was adjusted to 4-5 with concentrated hydrochloric acid (HCl) to quench the reaction, followed by extraction of the resulting precipitate with ethyl acetate (EtOAc, 3 x 50 mL). The organic phases were combined, dried over anhydrous sodium sulfate (Na2SO4), filtered and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (eluent: hexane-ethyl acetate, 3:1) to afford FMOC-12-aminododecanoic acid (4.20 g, 43% yield) as a white solid. The structure of the product was confirmed by 1H NMR and 13C NMR [28].
References
[1] Molecules, 2018, vol. 23, # 6,
