Lysine methylation within the N-terminal tail region of histones is associated with various biological processes ranging from transcriptional regulation to epigenetic silencing. In order to investigate biological functions of methylation, specific lysine dimethylated and trimethylated peptides derived from histone H3 N-terminal tail have been successfully synthesized by incorporating N α-Fmoc-N ε-dimethyl-lysine or N α-Fmoc-N ε-trimethyl-lysine as building blocks via solid-phase peptide synthesis. Facile synthesis of N α-Fmoc-N ε-dimethyl-lysine and N α-Fmoc-N ε-trimethyl-lysine have been presented. Reductive methylation of N α-Fmoc-lysine gives N α-Fmoc-N ε-dimethyl-lysine. Quaternisation of N α-Fmoc-lysine or N α-Fmoc-N ε-dimethyl-lysine produces N α-Fmoc-N ε-trimethyl-lysine as an iodide salt.
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Abbreviations
- Fmoc:
-
9-fluorenylmethoxycarbonyl
- ESI-MS:
-
electrospray ionization-mass spectroscopy
- HBTU:
-
2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluroniumhexafluorophosphate
- DIEA:
-
diisopropylethylamine
- HOBt:
-
1-hydroxybenzotriazole
- TFA:
-
trifluoroacetic acid
- RP-HPLC:
-
reversed-phase high-performance liquid chromatography.
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The authors would like to thank the financial supports from the National Natural Science Foundation of China (No. 20472041, No. 20532020 and NSFCBIC 20320130046).
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Huang, ZP., Du, JT., Zhao, YF. et al. Synthesis of Site-Specifically Dimethylated and Trimethylated Peptides Derived from Histone H3 N-Terminal Tail. Int J Pept Res Ther 12, 187–193 (2006). https://doi.org/10.1007/s10989-005-9006-z
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DOI: https://doi.org/10.1007/s10989-005-9006-z