L-Azidohomoalanine hydrochloride

L-Azidohomoalanine hydrochloride is an azide-containing unnatural amino acid^[1]. As a structural analog of methionine, L-Azidohomoalanine hydrochloride can be specifically incorporated into newly synthesized proteins during protein synthesis, and catalyzed by wild-type methionyl-tRNA synthetase (MetRS) without affecting protein degradation rates^[2][3]. L-Azidohomoalanine hydrochloride requires methionine-free medium for efficient labeling, and the incorporation efficiency competes with endogenous methionine levels^[4]. L-Azidohomoalanine hydrochloride is mainly used in the BONCAT (bioorthogonal noncanonical amino acid tagging) technology, which utilizes the chemical reaction of its azide group with alkyne or phosphine reagents to achieve fluorescent imaging, affinity purification, or mass spectrometry quantification of newly synthesized proteins, applicable to proteome dynamics studies from cells to live animals^[5][6][7].

References:
[1] Lang K, Chin JW. Cellular incorporation of unnatural amino acids and bioorthogonal labeling of proteins. Chem Rev. 2014;114(9):4764-4806.
[2] Dieterich DC, Link AJ, Graumann J, Tirrell DA, Schuman EM. Selective identification of newly synthesized proteins in mammalian cells using bioorthogonal noncanonical amino acid tagging (BONCAT). Proc Natl Acad Sci U S A. 2006;103(25):9482-9487.
[3] Wang J, Zhang J, Lee YM, et al. Nonradioactive quantification of autophagic protein degradation with L-azidohomoalanine labeling. Nat Protoc. 2017;12(2):279-288.
[4] Ma Y, McClatchy DB, Barkallah S, Wood WW, Yates JR 3rd. Quantitative analysis of newly synthesized proteins. Nat Protoc. 2018;13(8):1744-1762.
[5] Kern M, Ferreira-Cerca S. Differential Translation Activity Analysis Using Bioorthogonal Noncanonical Amino Acid Tagging (BONCAT) in Archaea. Methods Mol Biol. 2022;2533:229-246.
[6] Hatzenpichler R, Scheller S, Tavormina PL, Babin BM, Tirrell DA, Orphan VJ. In situ visualization of newly synthesized proteins in environmental microbes using amino acid tagging and click chemistry. Environ Microbiol. 2014;16(8):2568-2590.
[7] Hou Z, Han X, Wang Z, Ghazanfar S, Yang J, Liu H. A terminal alkyne and disulfide functionalized agarose resin specifically enriches azidohomoalanine labeled nascent proteins. J Chromatogr B Analyt Technol Biomed Life Sci. 2021;1165:122527.

L-Azidohomoalanine hydrochloride是一种含叠氮基团的非天然氨基酸^[1]。L-Azidohomoalanine hydrochloride作为甲硫氨酸的结构类似物，可在蛋白质合成过程中由野生型甲硫氨酰-tRNA合成酶（MetRS）催化，特异地整合到新合成的蛋白质中，且不影响蛋白质降解速率^[2][3]。L-Azidohomoalanine hydrochloride需要无甲硫氨酸培养基才能实现高效标记，其整合效率与内源性甲硫氨酸水平呈竞争关系^[4]。L-Azidohomoalanine hydrochloride主要用于BONCAT（生物正交非规范氨基酸标记）技术，利用其叠氮基团与炔基或膦酯试剂的化学反应，实现新合成蛋白质的荧光成像、亲和纯化或质谱定量，适用于从细胞到活体动物的蛋白质组动态研究^[5][6][7]。