4.3. Synthesis of TPEARG
The synthetic route was display in Figure S8. 347 mg, 1 mmol
1-(4-Aminophenyl)-1,2,2-triphenylethene and 649 mg, 1 mmol
Nα-Fmoc-Nω-(2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl)-L-arginine
was dissolved to 10 mL tetrahydrofuran(THF), then stirred in room
temperature under nitrogen protection for 10 min. 277 mg, 1 mmol
4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride was
added into the solution and reacted for another 3 h. Then, the THF was
removed by vacuum distillation. Then, the solid was added in to 5 mL
piperidine and 5 mL dichloromethane(DCM), then stirred in room
temperature under nitrogen protection for 2 h. The solvent was removed
by vacuum distillation. After that, 1 mL trifluoroacetic acid and 9 mL
DCM was added to the solid mixture and stirred for 1h. TPEARG was
purified by chromatography on silica gel with dichloromethane/
methanol(10:1) as faint yellow powder(9%). HRMS (ESI): m/z calcd for
C32H33N5O
[M]+ 504.2757, found in 504.2686.1H NMR (400 MHz, Methanol-d 4) δ
7.77 (d, J = 7.5 Hz, 1H), 7.63 (t, J = 7.3 Hz, 1H), 7.30
(ddd, J = 24.7, 16.3, 6.3 Hz, 4H), 7.07 (s, 4H), 7.00 (d,J = 12.2 Hz, 2H), 6.91 (s, 0H), 4.38 (d, J = 6.7 Hz, 1H),
4.18 (t, J = 8.8 Hz, 1H), 3.99 (s, 1H), 2.93 (s, 1H), 2.51 (d,J = 24.9 Hz, 3H), 2.02 (s, 2H), 1.40 (s, 3H), 0.88 (d, J =
4.3 Hz, 1H). 13C NMR (101 MHz, CDCl3)
δ 175.79, 170.45, 166.45, 161.24, 152.52, 145.08, 142.69, 140.92,
139.86, 133.39, 128.98, 128.71, 126.99, 121.71, 116.38, 110.92, 105.08,
64.55, 60.68, 49.63, 47.12, 39.51, 34.88, 29.54, 28.30, 28.10, 21.67,
18.16, 12.71, 11.58, 0.75, 0.37.