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Chemical name: N-epsilon-azido-L-lysine // Synonyms: 6-azido-L-norleucine, L-azidonorleucine, H-Nle(6-N3)-OH, (S)-6-azido-2-amino-hexanoic acid, L-azidolysine, Anl, Epsilon-azido-L-norleucine, H-Lys(N3)-OH
|Molecular weight:||172,19 g/mol|
H-Lys(N3)-OH is incorporated into proteins that can be further selectively modified using Staudinger ligation or Click-chemistry.
Presentation and Detection of Azide Functionality in Bacterial Cell Surface Proteins; A. J. Link, M. K. S. Vink, D. A. Tirrell; J. Am. Chem. Soc. 2004; 126(34): 10598-10602. https://doi.org/10.1021/ja047629c.
Discovery of aminoacyl-tRNA synthetase activity through cell-surface display of noncanonical amino acids; A. J. Link, M. K. S. Vink, N. J. Agard, J. A. Prescher, C. R. Bertozzi, D. A. Tirrell; PNAS 2006; 103(27): 10180-10185. https://doi.org/10.1073/pnas.0601167103.
Discovery of Escherichia coli methionyl-tRNA synthetase mutants for efficient labeling of proteins with azidonorleucine in vivo; I. C. Tanrikulu, E. Schmitt, Y. Mechulam, W. A. Goddard III, D. A. Tirrell; PNAS 2009; 106(36): 15285-15290. https://doi.org/10.1073/pnas.0905735106.
Orthogonal Alkynyl Amino Acid Reporter for Selective Labeling of Bacterial Proteomes during Infection; M. Grammel, M. M. Zhang, H. C. Hang; Angew. Chem. Int. Ed. 2010; 49(34): 5970-5974. https://doi.org/10.1002/anie.201002050.
Site-Specifically Phosphorylated Lysine Peptides; J. Bertran-Vicente, R. A. Serwa, M. Schümann, P. Schmieder, E. Krause, C. P. R. Hackenberger; J. Am. Chem. Soc. 2014; 136(39): 13622-13628. https://doi.org/10.1021/ja507886s.
Remote C-H Hydroxylation by an alpha-Ketoglutarate-Dependent Dioxygenase Enables Efficient Chemoenzymatic Synthesis of Manzacidin C and Proline Analogs; C. R. Zwick, H. Renata; J. Am. Chem. Soc. 2018; 140(3): 1165-1169. https://doi.org/10.1021/jacs.7b12918.
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