Tetrazine-Containing Amino Acid for Peptide Modification and Live Cell Labeling.
basic_science · Level V
Where this comes from
- Record sourced from PubMed, PMID 26536589.
- Also identified by DOI 10.1371/journal.pone.0141918 and PMC identifier 4633098.
- Licence recorded as CC BY.
- The licence permits redistribution, so the abstract is shown in full and the full text is available from the publisher.
Abstract
A novel amino acid derivative 3-(4-(1, 2, 4, 5-tetrazine-3-yl) phenyl)-2-aminopropanoic acid was synthesized in this study. The compound possessed better water-solubility and was synthesized more easily compared with the well-known and commercially available 3-(p-benzylamino)-1, 2, 4, 5-tetrazine. Tetrazine-containing amino acid showed excellent stability in biological media and might be used for cancer cell labeling. Moreover, the compound remained relatively stable in 50% TFA/DCM with little decomposition after prolonged exposure at room temperature. The compound could be utilized as phenylalanine or tyrosine analogue in peptide modification, and the tetrazine-containing peptide demonstrated more significant biological activity than that of the parent peptide. The combination of tetrazine group and amino acid offered broad development prospects of the bioorthogonal labeling and peptide synthesis.
Medical subject headings
- Amino Acids
- Heterocyclic Compounds, 1-Ring
- Intestinal Mucosa
- Lung Neoplasms
- Peptide Fragments
- Phenylalanine