, diluted with CHCl3 (10 mL), and washed with brine (three mL). The phases had been separated, and also the aqueous layer was extracted with CHCl3 (2 5 mL). The combined organic layers have been dried more than Na2SO4, along with the volatiles were removed under lowered stress. Purification of your residue by flash column chromatography (ten MeOH in CHCl3) afforded triazole (S)-10 as a white paste (28 mg, 77 ): Rf = 0.20 (10 CH3OH in CHCl3); the poor solubility of this amphiphilic compound at room temperature prevented us from acquiring trusted optical rotation data; max (film) 3332br (O-H, N-H), 1672s (CO) cm-1; 1H NMR (500 MHz, CDCl3/CD3OD, two:1) 0.84 (t, J = six.9 Hz, 6H, two CH2CH3), 1.17-1.36 (stack, 70H), 1.38-1.46 (stack, 2H), 1.52-1.75 [stack, 4H, C(12)H2 (middle of stack), C(14)HaHb (LHS of stack), C(14)HaHb (RHS of stack)], 2.01-2.09 [stack, 1H, C(three)HaHb], two.10- 2.22 [stack, 3H, C(three)HaHb, C(11)H2], two.71 [d, J = 12.eight Hz, 1H, C(18)HaH b], two.89 [dd, J = 12.8, 5.0 Hz, 1H, C(18)HaHb], three.13-3.19 [m, 1H, C(15)H], three.33-3.38 [stack, 2H, C(9)H2], three.47-3.71 [stack, 18H, such as C(1) HaHb, C(4)H2], three.73 [dd, J = ten.0, 5.0 Hz, 1H, C(1)HaHb], 3.75-3.79 (m, 1H), 4.17-4.22 [m, 1H, C(two)H], four.30 [dd, J = 7.8, 4.three Hz, 1H, C(16)H], four.48 [dd, J = 7.eight, four.8 Hz, 1H, C(17)H], 4.65 [s, 2H, C(three)H2], 5.27 [dd, J = eight.five, 6.five Hz, 1H, C(2)H], 7.99 [s, 1H, C(1)H], exchangeable hydrogens not observed; 13C NMR (125 MHz, CDCl3/CD3OD, two:1) 14.three [CH3, C(18), C(26) (resonance overlap)], 23.two (CH2), 26.1 [CH2, C(12)], 26.two (CH2), 26.4 (CH2), 28.8 [CH2, C(14)], [29.1, 29.5, 29.87, 29.90, 30.1, 30.19, 30.22, 32.five (CH2, alkyl chain, some resonance overlap)], 36.2 [CH2, C(11)], 39.8 [CH2, C(9)], 40.eight [CH2, C(18)], 51.three [CH, C(two)], 56.three [CH, C(15)], 60.9 [CH, C(17)], 62.6 [CH, C(16)], 63.9 [CH2, C(four)], 64.7 [CH, C(2)], 64.eight [CH2, C(3)], 70.17 [CH2, C(4)], 70.24 (CH2), 70.five (CH2), 70.6 (CH2), 70.8 (CH), 70.99 (CH2), 71.03 (CH2), 72.5 (CH), 72.Ofatumumab 8 (CH), 73.4 [CH2, C(1)], 75.0 [CH, C(3)], 123.3 [CH, C(1)], 145.three [C, C(2)], 165.1 (C, NHCONH), 169.1 [C, C(1)], 175.2 [C, C(ten)]; MS (TOF ES+) m/z 1276.8 ([M + Na]+, one hundred ), 649.9 (7), 398.1 (five); HRMS (TOF ES+) calcd for C67H127N7O12SNa [M + Na]+ 1276.9161, located 1276.9166. Fluor 488-Labeled -GalCer (11) (1:1 mixture of regioisomers inside the label). A CuSO4 option (6 L of a 0.five M option, three mol) as well as a sodium ascorbate solution (13 L of a 1.0 M answer, 13 mol) have been added to a resolution of azide 22 (1.4 mg, 1.Calcitonin (human) 7 mol) and alkyne 23 (1.PMID:23489613 0 mg, 1.7 mol) within a t-BuOH/H2O mixture (0.five mL, 1:1) at area temperature.dx.doi.org/10.1021/bc300556e | Bioconjugate Chem. 2013, 24, 586-Bioconjugate Chemistry The reaction mixture was heated for ten h at 50 , diluted with CHCl3 (5 mL), and washed with brine (1.5 mL). The phases had been separated, along with the aqueous layer was extracted with CHCl3 (2 2.5 mL). The combined organic layers had been dried over Na2SO4, as well as the volatiles had been removed under lowered stress. Purification of the residue by flash column chromatography (CHCl3/MeOH/H2O, 65:25:4) afforded triazole 11 as a red solid (1.4 mg, 59 , 1:1, mixture of regioisomers inside the label): Rf = 0.32 (CHCl3/MeOH/H2O, 65:25:4); 1H NMR (400 MHz, CDCl3/CD3OD, 2:1) 0.83 (t, J = six.7 Hz, 3H), 0.84 (t, J = six.7 Hz, 3H), 1.10-1.39 (stack, 44H), 1.40-1.65 (m, 1H), 1.65-1.89 (m, 1H), 1.92-2.03 (stack, 5H), 2.12-2.30 (1H, m), 2.66-2.79 (stack, 2H), three.46- three.79 (stack, 22H), three.86 (dd, J = 10.eight, 4.8 Hz, 1H), three.90 (br s, 1H), four.12-4.22 (m, 1H), 4.55-4.67 (m, 2H), 4.88 (d, J = three.six Hz, 1H), five.21-5.41 (stac.