使用N-（叔丁基二甲基甲硅烷基）[15N]邻苯二甲酰亚胺作为15N标记试剂高效合成[2-15N]鸟苷和2'-脱氧[2'-15N]鸟苷衍生物。

Efficient synthesis of [2-15N]guanosine and 2'-deoxy[2'-15N]guanosine derivatives using N-(tert-butyldimethylsilyl)[15N]phthalimide as a 15N-labeling reagent.

作者信息

Kamaike Kazuo, Kayama Yoshihiro, Mitsuhisa Isobe, Etsuko Kawashima

机构信息

School of Pharmarcy, Tokyo University of Pharmarcy and Life Sciences, Hachioji, Tokyo, Japan.

出版信息

Nucleosides Nucleotides Nucleic Acids. 2006;25(1):29-35. doi: 10.1080/15257770500377771.

DOI:10.1080/15257770500377771

PMID:16440983

Abstract

Nucleophilic aromatic substitution of 9-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)-6-chloro-2-fluoro-9H-purine with N-(tert-butyldimethylsilyl) [15N]phthalimide in the presence of a catalytic amount of CsF at room temperature in DMF efficiently afforded the 6-chloro-2-[15N]phthalimidopurine derivative, which was subsequently converted to the [2-15N]guanosine derivative. The 2'-deoxy[2'-15N]guanosine derivative was also efficiently synthesized through a similar procedure.

摘要

在室温下于N,N-二甲基甲酰胺（DMF）中，以催化量的氟化铯（CsF）为催化剂，9-(2,3,5-三-O-乙酰基-β-D-呋喃核糖基)-6-氯-2-氟-9H-嘌呤与N-(叔丁基二甲基硅烷基)[15N]邻苯二甲酰亚胺进行亲核芳香取代反应，高效地得到了6-氯-2-[15N]邻苯二甲酰亚胺基嘌呤衍生物，随后将其转化为[2-15N]鸟苷衍生物。通过类似的步骤也高效地合成了2'-脱氧[2'-15N]鸟苷衍生物。