Journal
TETRAHEDRON LETTERS
Volume 50, Issue 7, Pages 818-821Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2008.12.005
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Funding
- Scientific Research from the Ministry of Education, Sport, Science and Technology of Japan [20380069]
- Japan Society for the Promotion of Science [17GS0420]
- Grants-in-Aid for Scientific Research [20380069] Funding Source: KAKEN
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In one of the peptide condensation methods termed thioester method, an amino protecting group is required in the lysine side chain. In this study, to investigate the efficiency of the pyruvoyl group as an amino protecting group, we synthesized N(alpha)-fluorenylmethoxycarbonyl (Fmoc)-N(epsilon)-pyruvoyl-lysine and introduced it into peptides and glycopeptides by the ordinary Fmoc-based solid phase peptide synthesis. The pyruvoyl peptide could be condensed with a peptide thioester by the thioester method, and this protecting group was easily removed by o-phenylenediamine treatment without significant side reactions. (C) 2008 Elsevier Ltd. All rights reserved.
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