Photocrosslinking of DNA using 4-methylpyranocarbazole nucleoside with thymine base selectivity,Organic & Biomolecular Chemistry

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Photocrosslinking of DNA using 4-methylpyranocarbazole nucleoside with thymine base selectivity
Organic & Biomolecular Chemistry ( IF 2.9 ) Pub Date : 2021-09-09 , DOI: 10.1039/d1ob01621k
Jun-Ichi Mihara ₁ , Kenzo Fujimoto ₁

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This report describes a novel photocrosslinker, 4-methylpyranocarbazole nucleoside (^MEPK), that can be induced to crosslink using visible light. Previously, we reported a visible light-responsive artificial nucleic acid, pyranocarbazole nucleoside (^PCX). ^MEPK can selectively photocrosslink to thymine bases in a complementary nucleic acid strand. It was synthesized by introducing a methyl group at the 4-position of ^PCX, and it can differentiate between thymine and cytosine. The previously reported visible light-responsive artificial nucleic acid ^PCX has a low synthetic yield. ^MEPK was synthesized by Pechmann condensation which suppressed by-product formation, making the synthesis more efficient, and resulting in a higher yield than that of ^PCX. ^MEPK is expected to have practical applications as a photocrosslinker that can be manipulated with visible light and that selectively targets thymine bases.

中文翻译：

使用具有胸腺嘧啶碱基选择性的 4-甲基吡喃咔唑核苷光交联 DNA

本报告描述了一种新型光交联剂，即 4-甲基吡喃咔唑核苷 ( ^MEP K)，可使用可见光诱导交联。此前，我们报道了一种可见光响应的人工核酸，吡喃咔唑核苷（^PC X）。^MEP K 可以选择性地与互补核酸链中的胸腺嘧啶碱基进行光交联。^{它是通过在PC} X的 4 位引入甲基而合成的，它可以区分胸腺嘧啶和胞嘧啶。先前报道的可见光响应性人工核酸^PC X 的合成产率较低。^MEP K 由Pechmann 缩合合成它抑制了副产物的形成，使合成更有效，并导致比^PC X更高的产率^。MEP K 有望作为一种可以用可见光操作并选择性靶向胸腺嘧啶碱基的光交联剂具有实际应用。

更新日期：2021-09-17

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