FMOC-12-AMINODODECANOIC ACID Chemical Properties

Melting point:

102 °C

Boiling point:

628.8±28.0 °C(Predicted)

Density 

1.119±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

pka

4.78±0.10(Predicted)

form 

powder

color 

white

BRN 

9593537

Safety Information

Safety Statements 

22-24/25

WGK Germany 

3

FMOC-12-AMINODODECANOIC ACID Usage And Synthesis

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,

FMOC-12-AMINODODECANOIC ACID(128917-74-8)Related Product Information

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