带有 N-未取代 1,2,3-三唑-4-基部分的荧光 5-嘧啶核苷和 8-嘌呤核苷。
Fluorescent 5-Pyrimidine and 8-Purine Nucleosides Modified with an N-Unsubstituted 1,2,3-Triazol-4-yl Moiety.
机构信息
Department of Chemistry and Biochemistry , Florida International University , Miami , Florida 33199 , United States.
出版信息
J Org Chem. 2019 Mar 15;84(6):3624-3631. doi: 10.1021/acs.joc.8b03135. Epub 2019 Mar 6.
Abstract
The Cu(I)- or Ag(I)-catalyzed cycloaddition between 8-ethynyladenine or guanine nucleosides and TMSN gave 8-(1- H-1,2,3-triazol-4-yl) nucleosides in good yields. On the other hand, reactions of 5-ethynyluracil or cytosine nucleosides with TMSN led to the chemoselective formation of triazoles via Cu(I)-catalyzed cycloaddition or vinyl azides via Ag(I)-catalyzed hydroazidation. These nucleosides with a minimalistic triazolyl modification showed excellent fluorescent properties with 8-(1- H-1,2,3-triazol-4-yl)-2'-deoxyadenosine (8-TrzdA), exhibiting a quantum yield of 44%. The 8-TrzdA 5'-triphosphate was incorporated into duplex DNA containing a one-nucleotide gap by DNA polymerase β.
摘要
Cu(I)或 Ag(I)催化的 8-乙炔基腺嘌呤或鸟嘌呤核苷与 TMSN 的环加成反应以高产率得到 8-(1-H-1,2,3-三唑-4-基)核苷。另一方面，5-乙炔基尿嘧啶或胞嘧啶核苷与 TMSN 的反应通过 Cu(I)催化的环加成反应选择性地生成三唑，或通过 Ag(I)催化的水合叠氮化反应生成乙烯基叠氮化物。这些具有最小化三唑基修饰的核苷具有优异的荧光性质，其中 8-(1-H-1,2,3-三唑-4-基)-2'-脱氧腺苷(8-TrzdA)的量子产率为 44%。8-TrzdA 5'-三磷酸通过 DNA 聚合酶β掺入含有一个核苷酸缺口的双链 DNA 中。
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