caa a22 4500 463186176 CHVBK 20180406164853.0 cr unu---uuuuu 170326e20070701xx s 000 0 eng 10.1007/s00726-006-0442-7 doi (NATIONALLICENCE)springer-10.1007/s00726-006-0442-7 Concise preparation of N α-Fmoc- N ɛ-(Boc, methyl)-lysine and its application in the synthesis of site-specifically lysine monomethylated peptide [Elektronische Daten] [Z.-P. Huang, J.-T. Du, X.-Y. Su, Y.-X. Chen, Y.-F. Zhao, Y.-M. Li] Summary.: A concise preparation of N α-Fmoc-N ɛ-(Boc, methyl)-lysine and its application in the synthesis of site-specifically lysine monomethylated peptide is described. N α-Fmoc-N ɛ-(Boc, methyl)-lysine is obtained, via consecutive reductive benzylation and reductive methylation in a one-pot reaction, followed by debenzylation through catalytic hydrogenolysis and Boc protection in another one-pot reaction. A peptide containing monomethylated lysine is successfully synthesized by incorporating N α-Fmoc-N ɛ-(Boc, methyl)-lysine as a building block via solid-phase peptide synthesis. Springer-Verlag, 2006 Keywords: Lysine - Methylation - Benzylation - Monomethylated peptide - Synthesis nationallicence Fmoc : 9-fluorenylmethoxycarbonyl nationallicence Boc : tert-butyloxycarbonyl nationallicence TFA : trifluoroacetic acid nationallicence DIEA : N,N-diisopropylethylamine nationallicence DMF : N,N-dimethylformamide nationallicence TEA : triethylamine nationallicence HBTU : 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluroniumhexafluorophosphate nationallicence HOBt : hydroxybenzotriazole nationallicence SPPS : solid-phase peptide synthesis nationallicence ESI-MS : electrospray ionization-mass spectrometry nationallicence RP-HPLC : reversed-phase high-performance liquid chromatography nationallicence Huang Z.-P Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University, Beijing, China aut Du J.-T Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University, Beijing, China aut Su X.-Y Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University, Beijing, China aut Chen Y.-X Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University, Beijing, China aut Zhao Y.-F Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University, Beijing, China aut Li Y.-M Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University, Beijing, China aut Amino Acids Springer-Verlag 33/1(2007-07-01), 85-89 0939-4451 33:1<85 2007 33 726 https://doi.org/10.1007/s00726-006-0442-7 text/html Onlinezugriff via DOI 1 research-article jats NATIONALLICENCE 856 40 https://doi.org/10.1007/s00726-006-0442-7 text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Huang Z.-P Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University, Beijing, China aut NATIONALLICENCE 700 1- Du J.-T Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University, Beijing, China aut NATIONALLICENCE 700 1- Su X.-Y Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University, Beijing, China aut NATIONALLICENCE 700 1- Chen Y.-X Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University, Beijing, China aut NATIONALLICENCE 700 1- Zhao Y.-F Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University, Beijing, China aut NATIONALLICENCE 700 1- Li Y.-M Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University, Beijing, China aut NATIONALLICENCE 773 0- Amino Acids Springer-Verlag 33/1(2007-07-01), 85-89 0939-4451 33:1<85 2007 33 726 Metadata rights reserved Springer special CC-BY-NC licence nationallicence BK010053 XK010053 XK010000 NATIONALLICENCE NATIONALLICENCE NL-springer