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Convenient synthesis of nucleoside 5'-(α-P-thio)triphosphates and phosphorothioate nucleic acids(DNA and RNA) 被引量:3
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作者 CATON-WILLIAMS Julianne FIAZ Bilal +1 位作者 HOXHAJ Rudiona SMITH Matthew 《Science China Chemistry》 SCIE EI CAS 2012年第1期80-89,共10页
Modified deoxy-and ribo-nucleoside triphosphates are chemically synthesized in multiple steps due to the protection and deprotection of the nucleoside functionalities.To conveniently synthesize the S-modified triphosp... Modified deoxy-and ribo-nucleoside triphosphates are chemically synthesized in multiple steps due to the protection and deprotection of the nucleoside functionalities.To conveniently synthesize the S-modified triphosphates for enzymatically preparing phosphorothioate DNAs and RNAs(PS-DNA and PS-RNA) as potential therapeutics,herein we report a one-pot strategy to synthesize the deoxy-and ribo-nucleoside 5'-(α-P-thio)triphosphates(dNTPαS and NTPαS) without protecting any nucleoside functionalities.This facile synthesis is achieved by treating the nucleosides with a mild phosphitylating reagent,reacting selectively with the 5'-hydroxyl group of each unprotected nucleoside,followed by sulfurization and hydrolysis to afford the crude dNTPαS and NTPαS analogs(mixtures of Sp and Rp diastereomers).We also demonstrated that after just simple precipitation(without HPLC and ion-exchange purification),the quality of the synthesized dNTPαS and NTPαS analogs is excellent for direct DNA polymerization and RNA transcription,respectively.Since Klenow DNA polymerase and T7 RNA polymerase accept the Sp diastereomers of dNTPαS and NTPαS analogs,respectively,while the Rp diastereomers are neither substrates nor inhibitors,the diastereomerically-pure PS-DNAs and PS-RNAs can be conveniently synthesized enzymatically. 展开更多
关键词 sulfur modification S-derivatized nucleic acid nucleoside triphosphates nucleoside phosphorothioates phosphorothioate dna and RNA DIASTEREOMERS dna and RNA polymerases
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Twenty years hunting for sulfur in DNA 被引量:2
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作者 Shi Chen Lianrong Wang Zixin Deng 《Protein & Cell》 SCIE CSCD 2010年第1期14-21,共8页
Here we tell a 20-year long story.It began with an easily overlooked DNA degradation(Dnd)phenomenon during electrophoresis and eventually led to the discovery of an unprecedented DNA sulfur modification governed by fi... Here we tell a 20-year long story.It began with an easily overlooked DNA degradation(Dnd)phenomenon during electrophoresis and eventually led to the discovery of an unprecedented DNA sulfur modification governed by five dnd genes.This unusual DNA modification,called phosphorothioation,is the first physiological modification identified on the DNA backbone,in which the nonbridging oxygen is replaced by sulfur in a sequence selective and stereo-specific manner.Homologous dnd gene clusters have been identified in diverse and distantly related bacteria and thus have drawn immediate attention of the entire microbial scientific community.Here,we summarize the progress in chemical,genetic,enzymatic,bioinformatical and analytical aspects of this novel postreplicative DNA modification.We also discuss perspectives on the physiological functions of the DNA phosphorothioate modification in bacteria and their implications. 展开更多
关键词 dna sulfur modification dna phosphorothioate modification dna degradation
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