16-Azidohexadecanoic acid

16-azidohexadecanoic acid can be a substrate for observing the degradation of fatty acids (FAs)^[1]. 16-azidohexadecanoic acid contains an azide group, which can undergo the copper-catalyzed azide–alkyne cycloaddition (CuAAC) reaction, often called “click chemistry”. This methodology primarily aims to identify new drug development hits^[2]. 16-azidohexadecanoic acid can be conjugated with the HIV Tat 48–60 cell permeation peptide (CPP) under standard Fmoc solid-phase peptide synthesis conditions to produce an azido lipopeptide^[3]. The 16-azidohexadecanoic acid, which features an azide group, is capable of undergoing the strain-promoted alkyne–azide cycloaddition (SPAAC) reaction with molecules that contain a dibenzocyclooctyne (DBCO) moiety, enabling covalent linkage with azide-modified dNTP to obtain the functionalized nucleotide (dC^C16N3TP). The functionalized nucleotide (dC^C16N3TP) is a key intermediate in bioconjugation^[4].

References:
[1] Pérez AJ, Bode HB. ω-Azido fatty acids as probes to detect fatty acid biosynthesis, degradation, and modification. J Lipid Res. 2014;55(9):1897-1901.
[2] Carlucci R, Lisa MN, Labadie GR. 1,2,3-Triazoles in Biomolecular Crystallography: A Geometrical Data-Mining Approach. J Med Chem. 2023;66(21):14377-14390.
[3] Eltepu L, Jayaraman M, Rajeev KG, Manoharan M. An immobilized and reusable Cu(I) catalyst for metal ion-free conjugation of ligands to fully deprotected oligonucleotides through click reaction. Chem Commun (Camb). 2013;49(2):184-186.
[4] Balintová J, Welter M, Marx A. Antibody-nucleotide conjugate as a substrate for DNA polymerases. Chem Sci. 2018;9(35):7122-7125.

16-azidohexadecanoic acid可以作为底物，观察脂肪酸（FAs）的降解情况^[1]。16-azidohexadecanoic acid含有叠氮基团，能够发生铜催化的叠氮-炔烃环加成反应（CuAAC），这种反应通常被称为“点击化学”。这种方法主要用于寻找药物开发的新靶点^[2]。在标准的Fmoc固相肽合成条件下，16-azidohexadecanoic acid可以与HIV Tat 48–60细胞穿膜肽（CPP）偶联以产生叠氮脂肽^[3]。含有叠氮基团的16-azidohexadecanoic acid能够与含有二苯并环辛炔（DBCO）基团的分子发生应变促进的炔烃-叠氮环加成（SPAAC）反应，然后与叠氮修饰的dNTP共价连接，从而获得功能化核苷酸 (dC^C16N3TP)。功能化核苷酸(dC^C16N3TP)是用于生物偶联过程的关键中间体^[4]。