Lauric acid N-hydroxy-succinimide ester

Uses

(2,5-Dioxopyrrolidin-1-yl) dodecanoate is a biochemical reagent that can be used as a biological material or organic compound for life science related research.

Biochem/physiol Actions

Lauric acid N-hydroxysuccinimide ester may be used for the synthesis of N-acylamino acids and lipidization of polypeptides or other applications that use N-hydroxysuccinimide ester conjugation chemistry.

Synthesis

General procedure: lauric acid (12.0 g, 60 mmol) was dissolved in anhydrous ethyl acetate (100 mL), followed by slow addition of this solution to a solution of anhydrous ethyl acetate (300 mL) containing N-hydroxysuccinimide (NHS) (6.9 g, 60 mmol) and N,N'-dicyclohexylcarbodiimide (DCC) (12.4 g, 60 mmol). . The reaction mixture was stirred overnight at room temperature. After completion of the reaction, the by-product dicyclohexylurea (DCU) was removed by filtration. The filtrate was concentrated under reduced pressure to afford the white crystalline product 2,5-dioxopyrrolidin-1-yl dodecanoate (17.4 g, 95% yield). For further purification, the product was recrystallized with ethanol to give a final pure product of 16.6g.

References

[1] Journal of the American Chemical Society, 2015, vol. 137, # 24, p. 7692 - 7705
[2] Journal of the American Chemical Society, 2003, vol. 125, # 40, p. 12110 - 12111
[3] RSC Advances, 2015, vol. 5, # 81, p. 66339 - 66354
[4] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 6, p. 1763 - 1767
[5] Synthetic Communications, 2009, vol. 39, # 24, p. 4467 - 4472