含亲水性叠氮化物的氨基酸提高 SPAAC 反应中肽的溶解性
Hydrophilic Azide-Containing Amino Acid to Enhance the Solubility of Peptides for SPAAC Reactions.
机构信息
Chemical Biology Laboratory, Center for Cancer Research, National Cancer Institute, National Institutes of Health, Frederick, Maryland 21702, United States.
出版信息
Org Lett. 2022 Oct 14;24(40):7378-7382. doi: 10.1021/acs.orglett.2c02906. Epub 2022 Oct 3.
Abstract
We report a new positively charged azidoamino acid for strain-promoted azide-alkyne cycloaddition (SPAAC) applications that overcomes possible solubility limitations of commonly used azidolysine, especially in systems with numerous ligation sites. The residue is easily synthesized, is compatible with Fmoc-based solid-phase peptide synthesis employing a range of coupling conditions, and offers efficient second-order rate constants in SPAAC ligations employing DBCO (0.34 M s) and BCN (0.28 M s).
摘要
我们报道了一种新型的带正电荷的叠氮氨基酸，用于应变促进的叠氮-炔环加成（SPAAC）应用，克服了常用的叠氮赖氨酸可能存在的溶解度限制，尤其是在具有多个连接点的系统中。该残基易于合成，与采用多种偶联条件的 Fmoc 固相肽合成兼容，并在采用 DBCO（0.34 M s）和 BCN（0.28 M s）的 SPAAC 连接中提供高效的二级速率常数。
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