Tryptamine → L-Lysine
Reaktionsgleichung
[NH2:1][CH2:2][CH2:3][C:4]1[C:12]2[C:7](=CC=CC=2)[NH:6]C=1.C1C=CC2N([OH:22])N=NC=2C=1.C1CCC(N=C=NC2CCCCC2)CC1.CN([CH:41]=[O:42])C>>[NH2:1][C@H:2]([C:41]([OH:42])=[O:22])[CH2:3][CH2:4][CH2:12][CH2:7][NH2:6]Komponenten
5
Versuchsvorschrift
10 mmol of a methoxycarbonyl derivative of a basic amino acid with the L-configuration is dissolved in 30 ml of DMF, 3.2 g (20 mmol) of tryptamine, 1.54 g of HOBt (10 mmol, monohydrate) and 2.1 g of DCC (10.17 mmol) is added, and the mixture is stirred at the room temperature for 24 h. A DCU precipitate is then filtered off and the solvent evaporated. The oily residue is dissolved in 150 ml of ethyl acetate and washed with 150 ml of 10% aqueous Na2CO3, water, 1% citric acid (three times) and brine. The organic layer is dried (MgSO4), filtered and evaporated to dryness. The residue is purified by column chromatography (SiO2) with O:H phase 7:3+3% MeOH, to yield amide of tetrakis(methoxycarbonyl) derivative of lysine as a dark orange oil.