Both natural laminine and the synthesized substances, according to the A method: methylation of copper complex of L-lysine by dimethylsulfate, and to the B method: methylation of N
2-acetyl-L-lysine, followed by hydrolysis, were in good agreement in every respect. The reaction between 6-chloro-2-aminohexanoic acid and trimethylamine gave DL-laminine (oxalate, m.p. 129-130°, C
13H
24O
10N
2⋅1/2H
2O, colorless needles). Besides, trimethyl-(5-amino-1-carboxypentyl)-ammonium oxalate, m.p. 200°, [α]
D +8.4° (H
2O), C
20H
42O
8N
2⋅4H
2O, colorless needles, L-lysine betaine dipicrate, m.p. 217° (decomp.), C
24H
32O
16N
8, yellow platelets, trimethyl-(4-amino-4-carboxybutyl)-ammonium dioxalate, m.p. 111-113°, [α]
D+11.0° (H
2O), C
12H
22O
10N
2⋅H
2O and trimethyl-(3-amino-3-carboxypropyl)-ammonium oxalate, m.p. 181° (decomp.), [α]
D+10.4° (H
2O), C
9H
18O
6N
2 were synthesized.
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