A Modified Synthesis of α- N -carbobenzoxy-<scp>L</scp>-lysine and the preparation and analysis of mixtures of ε- N -methyllysines

α-N-Carbobenzoxy-L-lysine has been obtained in 37% yield by carbobenzoxylation of L-lysine in 25% excess benzaldehyde followed by passage of the solution through a cupric carbonate – alumina column. Reaction of the product in aqueous solution with diazomethane, followed by deprotection, gave a mixtu...

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Bibliographic Details
Published in:Canadian Journal of Biochemistry
Main Authors: Benoiton, N. Leo, Demayo, Ruth E., Moore, Graham J., Coggins, John R.
Format: Article in Journal/Newspaper
Language:English
Published: Canadian Science Publishing 1971
Subjects:
DML
Online Access:http://dx.doi.org/10.1139/o71-187
http://www.nrcresearchpress.com/doi/pdf/10.1139/o71-187
Description
Summary:α-N-Carbobenzoxy-L-lysine has been obtained in 37% yield by carbobenzoxylation of L-lysine in 25% excess benzaldehyde followed by passage of the solution through a cupric carbonate – alumina column. Reaction of the product in aqueous solution with diazomethane, followed by deprotection, gave a mixture of ε-N-methyllysine (MML), ε-N,ε-N-dimethyllysine (DML), and ε-N,ε-N,ε-N-trimethyllysine suitable as a standard for chromatographic purposes. It has been demonstrated that when a mixture of MML and DML emerges as one peak when chromatographed with an amino acid analyzer, the relative concentrations of the two amino acids in the mixture can be established from the 570/440 nm absorbance ratio.