Synthesis and Anti‐HIV Activity of a Series of 6‐Modified 2′,3′‐Dideoxyguanosine and 2′,3′‐Didehydro‐2′,3′‐dideoxyguanosine Analogs

Xie, Lujia; Yang, Xiantao; Pan, Delin; Cao, Yingli; Cao, Mou; Lin, Guichun; Zhu, Ge; Guo, Ying; Zhang, Lihe; Yang, Zhenjun

doi:10.1002/cjoc.201300440

Cited by 4 publications

(2 citation statements)

References 24 publications

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“…In addition, for adenine, guanine, and cytosine nucleobases, the exocyclic amino groups must be protected to prevent any side reactions . This method has also been applied to the synthesis of base-modified NTPs ,− and sugar-modified NTPs …”

Section: Nucleoside 5′-triphosphatesmentioning

confidence: 99%

Recent Trends in Nucleotide Synthesis

et al. 2016

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Focusing on the recent literature (since 2000), this review outlines the main synthetic approaches for the preparation of 5'-mono-, 5'-di-, and 5'-triphosphorylated nucleosides, also known as nucleotides, as well as several derivatives, namely, cyclic nucleotides and dinucleotides, dinucleoside 5',5'-polyphosphates, sugar nucleotides, and nucleolipids. Endogenous nucleotides and their analogues can be obtained enzymatically, which is often restricted to natural substrates, or chemically. In chemical synthesis, protected or unprotected nucleosides can be used as the starting material, depending on the nature of the reagents selected from P(III) or P(V) species. Both solution-phase and solid-support syntheses have been developed and are reported here. Although a considerable amount of research has been conducted in this field, further work is required because chemists are still faced with the challenge of developing a universal methodology that is compatible with a large variety of nucleoside analogues.

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Section: Nucleoside 5′-triphosphatesmentioning

confidence: 99%

Recent Trends in Nucleotide Synthesis

et al. 2016

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“…For the synthesis of dU*TP, the commercially available 5-iodo-2'-deoxyuridine was used as the starting material (Scheme 1). Although there were plenty of reports about triphosphorylation in recent years, [25,27,[44][45][46] challenges remain in the achievement of this critical step. [41][42][43] Then compound 1 reacted with propargyl alcohol via the Sonogashira coupling reaction for the introduction of hydroxyl group, with 2 as the product.…”

Section: Synthesis Of Deoxyuridine Triphosphate Analogue (Du*tp)mentioning

confidence: 99%

Primer Extension Reaction Assays for Incorporation of Deoxynucleotide Analogue into DNA

et al. 2015

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Incorporation of deoxynucleotide analogues into DNA is important for the expansion of DNA functions. Primer extension reactions are commonly used for the assay of such reaction events. However, current assay protocols generally rely on radiolabeling, fluorescence reporter labeling, or removal of specific deoxynucleotide triphosphate in the reaction mixture. Herein we report on the design of two novel assay protocols that utilize a dideoxynucleotide-terminated template strand and a phosphorothiolate-modified deoxynucleotide-terminated template strand. We designed and synthesized a deoxyuridine triphosphate analogue (dU*TP) containing 2-bromoisobutyryl group and demonstrated that it could be well recognized by φ29DNA polymerase, E. coli DNA polymerase I Klenow Fragment, Bst DNA polymerase Large Fragment, and E. coli DNA polymerase I Klenow Fragment (exo − ), which translated to effective incorporation of dU*TP into DNA. dU*TP was also successfully incorporated into extremely long single-stranded DNA at high-density using φ29 DNA polymerase by rolling circle amplification.

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