Labeling of DNA via rearrangement of S-2-aminoethyl phosphorothioates to N-(2-mercaptoethyl) phosphoramidates

Labeling of DNA via rearrangement of S-2-aminoethyl phosphorothioates to N-(2-mercaptoethyl) phosphoramidates
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DOI:
10.1039/b717664c
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发表时间:
2008-01-01
影响因子:
3.2
通讯作者:
Gothelf, Kurt V.
Gothelf, Kurt V.
中科院分区:
化学3区
文献类型:
--
作者:
Chen, Menglin;Gothelf, Kurt V.

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DNA中的硫代磷酸酯与2-溴乙基溴化铵反应产生S-2-氨基乙基硫代磷酸酯,其可以重排为N-(2-巯基乙基)氨基磷酸酯,提供了用于产生DNA序列的位点特异性巯基标记的简便方法。通过将巯基化DNA序列与N-α-(3-马来酰亚胺基丙酰基)生物胞素和Alexa Fluor 546 C5-马来酰亚胺缀合来证明该方法的适用性。
The reaction of phosphorothioates in DNA with 2-bromoethylammonium bromide results in S-2-aminoethyl phosphorothioates, which can rearrange to N-(2-mercaptoethyl) phosphoramidates providing a facile method for the generation of site-specific thiol labeling of DNA sequences. The applicability of this method was demonstrated by conjugation of the thiolated DNA sequence with N-alpha-(3-maleimidylpropionyl) biocytin and Alexa Fluor 546 C5-maleimide.