[NH:1]([C:20]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:21])[C@H:2]([C:10]([O:12]CC1C=CC=CC=1)=O)[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Cl.[NH2:31][CH2:32][C:33]([NH2:35])=[O:34].CCN(CC)CC>CN(C=O)C.O.CCOC(C)=O>[NH:1]([C:20]([O:22][CH2:23][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)=[O:21])[C@H:2]([C:10]([NH:31][CH2:32][C:33]([NH2:35])=[O:34])=[O:12])[CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1To a solution of Z-L-Phe-OBn (25, 19.2 mg, 0.05 mmol) in DMF (0.25 mL) and water (0.144 mL), glycinamide hydrochloride (31, 17 mg, 0.15 mmol) and Et3N (0.15 mmol, 0.0625 mL) were added, followed by the addition of S166C—S-inden-oxaz(S,R) (ME-n, 0.106 mL, 0.5 mg of active enzyme in 10 mM MES buffer (pH 5.8) including 1 mM CaCl2). The reaction was stirred for one hour at room temperature. The mixture was diluted with AcOEt and washed with 1 M KHSO4 (1 mL×1) and brine (1 mL×1), and the organic layer was dried over MgSO4. After evaporation, the residue was purified by preparative TLC (CH2Cl2/MeOH=90/10) to afford Z-L-Phe-Gly-NH2 (33, 17.8 mg, quantitative).
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