title: A convenient preparation of N (ε)-methyl-L-lysine derivatives and its application to the synthesis of histone tail peptides.
abstract: A convenient route is established for the preparation of N (α)-Fmoc-N (ε)-(Boc, methyl)-L-lysine and N (α)-Fmoc-N (ε)-dimethyl-L-lysine as building blocks to be used for the synthesis of methylated peptides. This methodology is based on the use of malonate derivatives and dibromobutane to produce key intermediates, L-2-amino-6-bromohexanoic acid derivatives, which could be modified to the required group at the ε-position. Fmoc-protection is accessible, so these compounds can be used in solution as well as in solid-phase peptide synthesis. Also the peptides containing these methylated lysines have been proved to resist the action of trypsin and lysyl endopeptidase. Thus, this new method could be considered as an improvement of the synthesis of N (ε)-methyl-L-lysine derivatives.
authors.affiliation: Graduate School of Life Science and Systems Engineering, Kyushu Institute of Technology, Wakamatsu, Kitakyushu, 808-0196, Japan.
authors.forename: Hongfang
authors.initials: H
authors.lastname: Chi
authors.forename: Md Shahidul
authors.initials: MS
authors.lastname: Islam
authors.forename: Tienabe K
authors.initials: TK
authors.lastname: Nsiama
authors.forename: Tamaki
authors.initials: T
authors.lastname: Kato
authors.forename: Norikazu
authors.initials: N
authors.lastname: Nishino
mesh_terms: D006657:Histones / Q000138:chemical synthesis* / Q000737:chemistry; D008239:Lysine / Q000031:analogs & derivatives / Q000737:chemistry*; D015394:Molecular Structure; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry; D060327:Solid-Phase Synthesis Techniques / Q000379:methods*
chemical_list: D006657:Histones; D010455:Peptides; D008239:Lysine