- 1,2,4-Triazine-Modified 2′-Deoxyuridine Triphosphate for Efficient Bioorthogonal Fluorescent Labeling of DNA
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In order to establish the Diels–Alder reaction with inverse electron demand for postsynthetic DNA modification, a 1,2,4-triazine-modified 2′-deoxyuridine triphosphate was synthesized. The bioorthogonally reactive 1,2,4-triazine group was attached at the 5-position of 2′-deoxyuridine by a flexible alkyl linker to facilitate its acceptance by DNA polymerases. The screening of four DNA polymerases showed successful primer extensions, using a mixture of dATP, dGTP, dCTP, and the modified 2′-deoxyuridine triphosphate, by using KOD XL or Vent polymerase. The triazine moiety was stable under the conditions of primer extension, which was evidenced by labeling with a BCN-modified rhodamine at room temperature in yields of up to 82 %. Two or three modified bases could be incorporated in quantitative yields when the modification sites were separated by three base pairs. These results establish the 1,2,4-triazene group as a bioorthogonally reactive moiety in DNA, thereby replacing the problematic 1,2,4,5-tetrazine for postsynthetic labeling by the Diels–Alder reaction with inverse electron demand.
- Peewasan, Krisana,Wagenknecht, Hans-Achim
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p. 1473 - 1476
(2017/08/09)
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- Synthesis of substituted fused pyridines, pyrazines and pyrimidines by sequential Ugi/inverse electron demand Diels-Alder transformations
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The synthesis of all four regioisomers of fused pyrrolidino-pyridines in a one-pot two-step sequential Ugi-inverse electron demand Diels-Alder reaction is described. Fused pyrrolidino-pyrazines, pyrrolidino-pyrimidines and azepinone pyridines can also be obtained in consecutive synthetic sequences.
- Akritopoulou-Zanze, Irini,Wang, Ying,Zhao, Hongyu,Djuric, Stevan W.
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scheme or table
p. 5773 - 5776
(2009/12/26)
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- Preparation of tetrahydroimidazo[2,1-a]isoquinolines and their use as inhibitors of gastric acid secretion
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A series of novel tetrahydroimidazo[2,1-a]isoquinolines was prepared based on a hetero Diels-Alder reaction between an enamine and 1,2,4-triazine as key step. A structure-activity relationship was established focussing on the influence of the substitution
- Palmer, Andreas Marc,Grobbel, Burkhard,Brehm, Christof,Zimmermann, Peter Jan,Buhr, Wilm,Feth, Martin Philipp,Holst, Hans Christof,Simon, Wolfgang Alexander
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p. 7647 - 7660
(2008/03/28)
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- Indole as a Dienophile in Inverse Electron Demand Diels-Alder Reactions: Reactions with 1,2,4-Triazines and 1,2-Diazines
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Indole reacts with 1,2,4-triazines in the absence of solvent or in the presence of limited amounts of solvent to produce β- or γ-carbolines, benzonaphthyridines, or the noncyclized 3-indoles.The combined yields of cycloadducts with tricarbalkoxytriazines exceeds 90 percent, with the production of γ-carbolines exceeding 80 percent.The regiochemistry of the adduct and the ratio of the products is determined mainly by electronic effects of the triazine substituents.Indole also ungergoes a cyclocondensation reaction with tetramethyl 1,2-diazine-3,4,5,6-tetracarboxylate to give trimethyl 5H-6-oxophenanthridine-2,3,4-tricarboxylate.
- Benson, Scott C.,Gross, Jonathan L.,Snyder, John K.
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p. 3257 - 3269
(2007/10/02)
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