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1,3-二酮修饰核苷酸和 DNA 与含精氨酸的肽和蛋白质的交联。

1,3-Diketone-Modified Nucleotides and DNA for Cross-Linking with Arginine-Containing Peptides and Proteins.

机构信息

Institute of Organic Chemistry and Biochemistry, Czech Academy of Sciences, Flemingovo nam. 2, 16610, Prague 6, Czech Republic.

Department of Organic Chemistry, Faculty of Science, Charles University in Prague, Hlavova 8, 12843, Prague 2, Czech Republic.

出版信息

Angew Chem Int Ed Engl. 2021 Aug 2;60(32):17383-17387. doi: 10.1002/anie.202105126. Epub 2021 Jul 2.

DOI:10.1002/anie.202105126
PMID:34107150
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC8362068/
Abstract

Linear or branched 1,3-diketone-linked thymidine 5'-O-mono- and triphosphate were synthesized through CuAAC click reaction of diketone-alkynes with 5-azidomethyl-dUMP or -dUTP. The triphosphates were good substrates for KOD XL DNA polymerase in primer extension synthesis of modified DNA. The nucleotide bearing linear 3,5-dioxohexyl group (HDO) efficiently reacted with arginine-containing peptides to form stable pyrimidine-linked conjugates, whereas the branched 2-acetyl-3-oxo-butyl (PDO) group was not reactive. Reaction with Lys or a terminal amino group formed enamine adducts that were prone to hydrolysis. This reactive HDO modification in DNA was used for bioconjugations and cross-linking with Arg-containing peptides or proteins (e.g. histones).

摘要

线性或支化的 1,3-二酮连接的胸苷 5'-O-单和三磷酸酯通过二酮-炔与 5-叠氮甲基-dUMP 或 -dUTP 的 CuAAC 点击反应合成。三磷酸酯是 KOD XL DNA 聚合酶在修饰 DNA 的引物延伸合成中的良好底物。带有线性 3,5-二氧代己基的核苷酸（HDO）与含精氨酸的肽有效反应，形成稳定的嘧啶连接的缀合物，而支化的 2-乙酰基-3-氧代丁基（PDO）基团则没有反应性。与赖氨酸或末端氨基反应形成烯胺加合物，容易水解。这种在 DNA 中的反应性 HDO 修饰用于与含精氨酸的肽或蛋白质（例如组蛋白）进行生物偶联和交联。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d508/8362068/0b8fb01526a2/ANIE-60-17383-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d508/8362068/e8a10bf22432/ANIE-60-17383-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d508/8362068/8a1ed69eaf49/ANIE-60-17383-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d508/8362068/0b8fb01526a2/ANIE-60-17383-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d508/8362068/e8a10bf22432/ANIE-60-17383-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d508/8362068/8a1ed69eaf49/ANIE-60-17383-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d508/8362068/0b8fb01526a2/ANIE-60-17383-g002.jpg

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