A convenient preparation of N super( epsilon )-methyl-l-lysine derivatives and its application to the synthesis of histone tail peptides

A convenient route is established for the preparation of N super( alpha )-Fmoc-N super( epsilon )-(Boc, methyl)-l-lysine and N super( alpha )-Fmoc-N super( epsilon )-dimethyl-l-lysine as building blocks to be used for the synthesis of methylated peptides. This methodology is based on the use of malo...

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Bibliographic Details
Published in:Amino acids 2014-05, Vol.46 (5), p.1305-1311
Main Authors: Chi, Hongfang, Islam, MdShahidul, Nsiama, Tienabe K, Kato, Tamaki, Nishino, Norikazu
Format: Article
Language:English
Subjects:
Accessibility
Amino acids
Derivatives
Histones
Lysine
Peptides
Synthesis
Trypsin
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Summary:A convenient route is established for the preparation of N super( alpha )-Fmoc-N super( epsilon )-(Boc, methyl)-l-lysine and N super( alpha )-Fmoc-N super( epsilon )-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 epsilon -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 super( epsilon )-methyl-l-lysine derivatives.
ISSN:0939-4451
1438-2199
DOI:10.1007/s00726-014-1690-6