17 to 3.54 (6H, br, -NHCH 2 -), 4.18 to 4.48 (6H, br, -CH 2 CH(CH2SH)O-), 5.77 (3H, br, -CH2CH(CH2SH)O-), 8.03 (3H, br, -NH-). 13C-NMR (CDCl3/CF3CO2H = 5:1, rt, σ in ppm): 10.37 (−CH(CH2 CH3)(CH2)3CH3), 13.66 (−CH(CH2CH3) (CH2)3 CH3), 22.86 (−CH(CH2CH3) (CH2CH2 CH2CH3)), 23.98 (−CH(CH2CH3) (CH2CH2CH2CH3)), 26.08 (−CH2SH), 28.67 (−CH(CH2CH3) (CH2 selleck CH2CH2CH3)), 30.79 (−CH(CH2CH3) (CH2CH2CH2CH3)), 38.88 (−CH(CH2CH3) (CH2CH2CH2CH3)), 45.70 (−CH2CH(CH2SH)O–), 47.17 (−NHCH2-), 79.22 (−CH2 CH(CH2SH)O-), 149.37 (C=O), 187.66 (C=S). IR (KBr, cm−1): 3,326 (NH), 2,573 (SH) 1,698

(C=O), 1,172 (C=S). Polycondensation of TSHs and Zn(OAc)2 (typical procedure) To a flask containing OTSH (268 mg, 201 μmol), a 1,4-dioxane solution (5.0 mL) of Zn(OAc)2 (55 mg, 300 μmol) was added under a nitrogen atmosphere. The mixture was stirred at 60°C for 24 h. The GSK3326595 supplier mixture was poured into an excess amount of methanol, and the precipitate was

collected by filtration and drying under reduced pressure after washing with cold diethyl ether (131 mg, 91.7 μmol/unit, 45.3%). 1H-NMR (CDCl3/CF3CO2H = 5:1, δ in ppm): 0.88 (9H, t, J = 7.0 Hz, -CH 3 ), 1.27 (90H, -(CH 2 )15CH3), 1.61 to 1.74 (6H, -CH2CH 2 (CH2)15-), 2.87 (6H, -CHCH 2 SH), 3.17 to 3.46 (6H, -NHCH 2 CH2-), 4.26 to 4.59 (6H, -NCH 2 CH-), 5.59 (3H, -CH2CHO-), 6.62 (3H, -(C=S)NHCH2-). 13C-NMR (CDCl3/CF3CO2H = 5:1, δ in ppm): 13.76 (−CH2 CH3), 22.64 (−(CH2)15 CH2CH3), 26.64

(−CHCH2S-), 29.18 to 31.98 (−CH2(CH2)15CH2-), 45.24 (−NCH2CH-), 49.75 (−NHCH2(CH2)15-), 76.54 to 77.17 (−CH2 CHO-), 149.15 (C=O), 183.28 (C=S). IR (KBr, cm−1): 3,344 (NH), 1,697 (C=O), 1,160 (C=S). Other TSHs were also polymerized in the same procedure: Oxymatrine (1) BTZnS: yield = 64%, IR (KBr, cm−1): 3,393 (NH), 1,696 (C=O), 1,160 (C=S).   (2) HTZnS: yield = 62%, IR (KBr, cm−1): 3,327 (NH), 1,696 (C=O), 1,163 (C=S).   (3) IAZnS: yield = 68%, IR (KBr, cm−1): 3,317 (NH), 1,698 (C=O), 1,171 (C=S).   (4) EHTZnS: yield = 62%, IR (KBr, cm−1): 3,374 (NH), 1,698 (C=O), 1,168 (C=S).   Results and discussion Synthesis of TSH monomers Five TSHs were prepared via the reaction of TDT with amines according to the previous report (Figure 1) [29]. The resulting thiols obtained from XL184 octadecylamine, benzylamine, n-hexylamine, isoamylamine, and 2-ethylhexylamine are abbreviated as OTSH, BTSH, HTSH, IATSH, and EHTSH, respectively. The isolated yields were moderate or good (OTSH 76%, BTSH 84%, HTSH 85%, IATSH 41%, and EHTSH 78%). OTSH, BTSH, HTSH, and IATSH are solid stably storable under air atmosphere, but EHTSH is an unstable viscous oil, which is gradually oxidized by oxygen. Figure 1 Synthesis of OTSH, BTSH, HTSH, IATSH, and EHTSH.