Description
Benzyl (5-hydroxypentyl)carbamate is a linker capable of repairing damaged DNA by binding to the 5'-hydroxyl group on the sugar backbone. It can also bind to DNA ligands and can inhibit cell proliferation in resistant cell lines. However, benzyl (5-hydroxypentyl)carbamate is toxic to cells and can also cause DNA damage and strand breakage.
Chemical Properties
White Solid
Uses
Benzyl (5-hydroxypentyl)carbamate is a linker capable of repairing damaged DNA by binding to the 5'-hydroxyl group on the sugar backbone. Benzyl (5-hydroxypentyl)carbamate can also bind to DNA ligands and can inhibit cell proliferation in resistant cell lines. However, Benzyl (5-hydroxypentyl)carbamate is toxic to cells and can also cause DNA damage and strand breakage.
Synthesis
To a stirred mixture of 5-amino-1-pentanol (48.5 mmol, 5.0 g) and sodium bicarbonate (145.4 mmol, 12.2 g) in water (26 mL) was slowly added a solution of benzyl chloroformate (63.1 mmol, 9.0 mL) in THF (26 mL) dropwise at 0-5 °C. After the dropwise addition was completed, the reaction mixture was stirred at room temperature overnight. After completion of the reaction, the organic layer was separated by diluting the reaction mixture with EtOAc and water. The organic layer was washed with brine (2 x 30 mL), dried over anhydrous MgSO4, filtered and concentrated under reduced pressure to remove the solvent. The crude product was dispersed with a minimal amount of cyclohexane and the resulting solid was filtered and dried under vacuum to give 5-(Cbz-amino)-1-pentanol as a white solid (8.2 g, 71%).1H NMR (400 MHz, CDCl3) δ 7.35 (m, 5H), 5.09 (s, 2H), 4.8 (brs, 1H), 3.65 (m, 2H), and 3.20 (m, 2H), 1.50-1.58 (m, 6H), 1.39 (m, 2H).
References
[1] Journal of the American Chemical Society, 2006, vol. 128, # 12, p. 4058 - 4073
[2] Chemical Communications, 2010, vol. 46, # 48, p. 9119 - 9121
[3] Chemistry - A European Journal, 2010, vol. 16, # 6, p. 1754 - 1760
[4] European Journal of Organic Chemistry, 2011, # 12, p. 2346 - 2353
[5] Journal of Medicinal Chemistry, 2002, vol. 45, # 23, p. 5098 - 5111
