Concise preparation of N(alpha)-Fmoc-N(epsilon)-(Boc, methyl)-lysine and its application in the synthesis of site-specifically lysine monomethylated peptide.
A concise preparation of N(alpha)-Fmoc-N(epsilon)-(Boc, methyl)-lysine and its application in the synthesis of site-specifically lysine monomethylated peptide is described. N (alpha)-Fmoc-N(epsilon)-(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(alpha)-Fmoc-N(epsilon)-(Boc, methyl)-lysine as a building block via solid-phase peptide synthesis.
Huang
Z-P
ZP
Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University, Beijing, China.
Du
J-T
JT
Su
X-Y
XY
Chen
Y-X
YX
Zhao
Y-F
YF
Li
Y-M
YM
D000596:Amino Acids / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid; D005449:Fluorenes / Q000737:chemistry*; D008239:Lysine / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D010446:Peptide Fragments / Q000138:chemical synthesis* / Q000737:chemistry
D000596:Amino Acids; D005449:Fluorenes; C016456:N(alpha)-fluorenylmethyloxycarbonylamino acids; D010446:Peptide Fragments; D008239:Lysine