YAKUGAKU ZASSHI
Online ISSN : 1347-5231
Print ISSN : 0031-6903
ISSN-L : 0031-6903
Studies on the Hypotensive Constituents of Marine Algae. II
Synthesis of Laminine and Related Compounds
Tsunematsu TakemotoKoji DaigoNobuya Takagi
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1964 Volume 84 Issue 12 Pages 1180-1182

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Abstract
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 N2-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°, C13H24O10N2⋅1/2H2O, colorless needles). Besides, trimethyl-(5-amino-1-carboxypentyl)-ammonium oxalate, m.p. 200°, [α]D +8.4° (H2O), C20H42O8N2⋅4H2O, colorless needles, L-lysine betaine dipicrate, m.p. 217° (decomp.), C24H32O16N8, yellow platelets, trimethyl-(4-amino-4-carboxybutyl)-ammonium dioxalate, m.p. 111-113°, [α]D+11.0° (H2O), C12H22O10N2⋅H2O and trimethyl-(3-amino-3-carboxypropyl)-ammonium oxalate, m.p. 181° (decomp.), [α]D+10.4° (H2O), C9H18O6N2 were synthesized.
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