دورية أكاديمية
Synthesis of 4-Cyanoindole Nucleosides, 4-Cyanoindole-2'-Deoxyribonucleoside-5'-Triphosphate (4CIN-TP), and Enzymatic Incorporation of 4CIN-TP into DNA.
| العنوان: | Synthesis of 4-Cyanoindole Nucleosides, 4-Cyanoindole-2'-Deoxyribonucleoside-5'-Triphosphate (4CIN-TP), and Enzymatic Incorporation of 4CIN-TP into DNA. |
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| المؤلفون: | Passow KT; Department of Medicinal Chemistry, University of Minnesota, Minneapolis, Minnesota., Antczak NM; Department of Health Sciences and Technology, ETH Zurich, Zurich, Switzerland., Sturla SJ; Department of Health Sciences and Technology, ETH Zurich, Zurich, Switzerland., Harki DA; Department of Medicinal Chemistry, University of Minnesota, Minneapolis, Minnesota. |
| المصدر: | Current protocols in nucleic acid chemistry [Curr Protoc Nucleic Acid Chem] 2020 Mar; Vol. 80 (1), pp. e101. |
| نوع المنشور: | Journal Article; Research Support, N.I.H., Extramural; Research Support, Non-U.S. Gov't |
| اللغة: | English |
| بيانات الدورية: | Country of Publication: United States NLM ID: 101287865 Publication Model: Print Cited Medium: Internet ISSN: 1934-9289 (Electronic) Linking ISSN: 19349270 NLM ISO Abbreviation: Curr Protoc Nucleic Acid Chem Subsets: MEDLINE |
| مواضيع طبية MeSH: | Cyanides/*chemistry , DNA/*chemistry , Deoxyribonucleosides/*chemistry , Indoles/*chemistry , Nucleosides/*chemical synthesis, Carbon-13 Magnetic Resonance Spectroscopy ; Mass Spectrometry ; Nucleosides/chemistry ; Proton Magnetic Resonance Spectroscopy |
| مستخلص: | 4-Cyanoindole-2'-deoxyribonucleoside (4CIN) is a fluorescent isomorphic nucleoside analogue with superior spectroscopic properties in terms of Stokes shift and quantum yield in comparison to the widely utilized isomorphic nucleoside analogue, 2-aminopurine-2'-deoxyribonucleoside (2APN). Notably, when inserted into single- or double-stranded DNA, 4CIN experiences substantially less in-strand fluorescence quenching compared to 2APN. Given the utility of these properties for a spectrum of research applications involving oligonucleotides and oligonucleotide-protein interactions (e.g., enzymatic processes, DNA hybridization, DNA damage), we envision that additional reagents based on 4-cyanoindole nucleosides may be widely utilized. This protocol expands on the previously published synthesis of 4CIN to include synthetic routes to both 4-cyanoindole-ribonucleoside (4CINr) and 4-cyanoindole-2'-deoxyribonucleoside-5'-triphosphate (4CIN-TP), as well as a method for the enzymatic incorporation of 4CIN-TP into DNA by a polymerase. These methods are anticipated to further enable the utilization of 4CIN in diverse applications involving DNA and RNA oligonucleotides. © 2020 by John Wiley & Sons, Inc. Basic Protocol 1: Synthesis of 4-cyanoindole-2'-deoxyribonucleoside (4CIN) and 4CIN phosphoramidite 4 Basic Protocol 2: Synthesis of 4-cyanoindole-ribonucleoside (4CINr) Basic Protocol 3: Synthesis of 4-cyanoindole-2'-deoxyribonucleoside-5'-triphosphate (4CIN-TP) Basic Protocol 4: Steady state incorporation kinetics of 2AP-TP and 4CIN-TP by a DNA polymerase. (© 2020 John Wiley & Sons, Inc.) |
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| معلومات مُعتمدة: | P30 CA077598 United States CA NCI NIH HHS; R01 GM110129 United States GM NIGMS NIH HHS |
| فهرسة مساهمة: | Keywords: 4-cyanoindole; fluorescent nucleosides; polymerase incorporation |
| المشرفين على المادة: | 0 (Cyanides) 0 (Deoxyribonucleosides) 0 (Indoles) 0 (Nucleosides) 9007-49-2 (DNA) |
| تواريخ الأحداث: | Date Created: 20200108 Date Completed: 20210503 Latest Revision: 20210503 |
| رمز التحديث: | 20240628 |
| مُعرف محوري في PubMed: | PMC6954007 |
| DOI: | 10.1002/cpnc.101 |
| PMID: | 31909864 |
| قاعدة البيانات: | MEDLINE |
| تدمد: | 1934-9289 |
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| DOI: | 10.1002/cpnc.101 |