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Iminoboronate-Mediated Peptide Cyclization with Lysine Homologues
- Source :
- Synlett. 28:1913-1916
- Publication Year :
- 2017
- Publisher :
- Georg Thieme Verlag KG, 2017.
-
Abstract
- Cyclic peptides are attracting attention of medicinal chemists due to their increased stability in biological milieu as well as improved target binding affinities. Our laboratory has recently reported a powerful cyclization strategy that takes advantage of the spontaneous and reversible conjugation of lysine and a designed amino acid AB3 to give iminoboronates. Herein we report that Dap, a short chain homologue of lysine, displays significantly higher propensity to form imino­boronates and consequently improves the efficiency of peptide cyclization. Importantly, the preferential conjugation of AB3 to Dap allows a facile synthesis of cyclic peptides with free lysine residues.
Details
- ISSN :
- 14372096 and 09365214
- Volume :
- 28
- Database :
- OpenAIRE
- Journal :
- Synlett
- Accession number :
- edsair.doi...........173d1305e256341681b30e54a0dfe720