Bis(NHS)PEG5

• Bis(NHS)PEG5 [B3728]
• Benzylamine (= BnNH₂) [B0406]
• Triethylamine (= Et₃N) [T0424]
• Acetonitrile

To a solution of triethylamine (4.7 mL, 34.2 mmol) and benzylamine (620 µL, 5.6 mmol) in acetonitrile (39 mL) was added bis(NHS)PEG5 (1.0 g, 1.9 mmol) dissolved in acetonitrile (39 mL) at room temperature and stirred for 17 hours. The reaction mixture was washed with brine (30 mL), and the organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude product was purified by silica gel chromatography (dichloromethane:methanol = 8:1) to afford bis(Bn)PEG5 (638 mg, 66% yield) as a colorless clear oil.

The reaction solution was monitored by UPLC.

Bis(Bn)PEG5

¹H NMR (400 MHz, CDCl₃); δ 8.37 (t, J = 6.0 Hz, 2H), 7.33-7.21 (m, 10H), 4.27 (d, J = 6.0 Hz, 2H), 3.63 (t, J = 6.4 Hz, 2H), 3.49 (s, 16H), 3.35 (s, 2H), 2.38 (t, J = 6.4 Hz, 4H).

• Immunoactivity of Protein Conjugates of Carba Analogues from Neisseria meningitidis A Capsular Polysaccharide
• Q. GaO, M. Tontini, G. Brogioni, A. Nilo, S. Filippini, C. Harfouche, L. Polito, M. R. Romano, P. Costantino, F. Berti, R. Adamo, L. Lay, ACS Chem. Biol. 2013, 8, 2561.