(2S,4R)-N-[(1S)-2-hydroxy-1-[(3R,4S,5R,6R)-3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl]propyl]-1-methyl-4-propylpyrrolidine-2-carboxamide → Lincomycin
反応式
[CH3:1][CH2:2][CH2:3][C@H:4]1[CH2:8][N:7]([CH3:9])[C@H:6]([C:10]([NH:12][C@@H:13]([CH:25]([OH:27])[CH3:26])[CH:14]2[O:19][C@H:18]([S:20][CH3:21])[C@H:17]([OH:22])[C@@H:16]([OH:23])[C@H:15]2[OH:24])=[O:11])[CH2:5]1.CCC1CN(C)C(C(NC(C(O)C)C2OC(SC)C(O)C(O)C2O)=O)C1>>[CH3:1][CH2:2][CH2:3][C@H:4]1[CH2:8][N:7]([CH3:9])[C@H:6]([C:10]([NH:12][C@H:13]([C@H:25]([OH:27])[CH3:26])[C@H:14]2[O:19][C@H:18]([S:20][CH3:21])[C@H:17]([OH:22])[C@@H:16]([OH:23])[C@H:15]2[OH:24])=[O:11])[CH2:5]1参加物
3
実験手順
A crude crystalline lincomycin A preparation contained 20% of lincomycin B; the remaining solid material was primarily A. This starting material is used for twenty 18 g runs over two Prep PAK C18 cartridges eluted isocratically with (2:1) water-methanol. Pool cuts are made. The B rich pool is concentrated to an aqueous to which enough methanol is added to make a mobile phase; this is reinjected into the Prep 500. Rich eluent from the second hpplc is concentrated as before and rechromatographed a third time. Yield: 24 g of ~99% pure lincomycin B and ca. 125 g of highly pure lincomycin A. The entire isolation scheme is outlined in Chart 2.