Canaline is a derivative of ornithine, a naturally occurring amino acid with an O-alkyl hydroxylamine side chain that is produced by arginase from Canavanine. Due to its toxicity, by its ability to form oximes with carbonyl-containing biomolecules, it is produced by legumes as protection from herbivores. L-Canaline possesses anti-tumor activity against human acute leukemia T-cells, and as a result is of interest in cancer research. It also possesses antimalarial and antineoplastic properties.
Fmoc-Can(Trt) is a unit for conventional Fmoc-SPPS of canaline (Can)-containing peptides
generally applied for oxime ligation.1,2 Surprisingly, it was recently reported that such
peptides are spontaneously cleaved into two fragments via intramolecular cyclization reaction
at Can under very specific conditions (pH ca. 4-5).3 Can will be applied to not only
traditional medicinal chemistry and oxime-based bioconjugation but also various chemical
biology-oriented research in future.
1. F. Liu, et al., ChemBioChem, 9, 2000 (2008).
2. C.M. Haney, et al., Chem. Commun., 47, 10915 (2011).
3. S. Tsuda, et al., Chem. Commun., 54, 8861 (2018).
