title: Tetrazine-Containing Amino Acid for Peptide Modification and Live Cell Labeling.
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.
authors.affiliation: Institute of Biochemistry and Molecular Biology, School of Life Sciences, Lanzhou University, Lanzhou, China.
authors.forename: Zhongqiu
authors.initials: Z
authors.lastname: Ni
authors.affiliation: The Core Laboratory of the First Affiliated Hospital, Lanzhou University, Lanzhou, China.|Key Laboratory for Gastrointestinal Diseases of Gansu Province, Lanzhou University, Lanzhou, China.
authors.forename: Lanxia
authors.initials: L
authors.lastname: Zhou
authors.affiliation: Institute of Biochemistry and Molecular Biology, School of Life Sciences, Lanzhou University, Lanzhou, China.
authors.forename: Xu
authors.initials: X
authors.lastname: Li
authors.affiliation: Institute of Biochemistry and Molecular Biology, School of Life Sciences, Lanzhou University, Lanzhou, China.
authors.forename: Jing
authors.initials: J
authors.lastname: Zhang
authors.affiliation: Institute of Biochemistry and Molecular Biology, School of Life Sciences, Lanzhou University, Lanzhou, China.|Key Laboratory of Preclinical Study for New Drugs of Gansu Province, Lanzhou University, Lanzhou, China.
authors.forename: Shouliang
authors.initials: S
authors.lastname: Dong
mesh_terms: D000596:Amino Acids / Q000737:chemistry*; D000818:Animals; D006573:Heterocyclic Compounds, 1-Ring / Q000737:chemistry* / Q000493:pharmacokinetics*; D006801:Humans; D007413:Intestinal Mucosa / Q000378:metabolism*; D008175:Lung Neoplasms / Q000378:metabolism* / Q000473:pathology; D008297:Male; D051379:Mice; D010446:Peptide Fragments / Q000737:chemistry*; D010649:Phenylalanine / Q000031:analogs & derivatives* / Q000737:chemistry / Q000493:pharmacokinetics; D014018:Tissue Distribution; D014407:Tumor Cells, Cultured
chemical_list: D000596:Amino Acids; D006573:Heterocyclic Compounds, 1-Ring; D010446:Peptide Fragments; C000598289:tetrazine dye 10; D010649:Phenylalanine