Article ; Online: A convenient preparation of N (ε)-methyl-L-lysine derivatives and its application to the synthesis of histone tail peptides.
2014 Volume 46, Issue 5, Page(s) 1305–1311
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 ... ...
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. |
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MeSH term(s) | Histones/chemical synthesis ; Histones/chemistry ; Lysine/analogs & derivatives ; Lysine/chemistry ; Molecular Structure ; Peptides/chemical synthesis ; Peptides/chemistry ; Solid-Phase Synthesis Techniques/methods |
Chemical Substances | Histones ; Peptides ; Lysine (K3Z4F929H6) |
Language | English |
Publishing date | 2014-05 |
Publishing country | Austria |
Document type | Evaluation Studies ; Journal Article |
ZDB-ID | 1121341-3 |
ISSN | 1438-2199 ; 0939-4451 |
ISSN (online) | 1438-2199 |
ISSN | 0939-4451 |
DOI | 10.1007/s00726-014-1690-6 |
Database | MEDical Literature Analysis and Retrieval System OnLINE |
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