Kvaernø L, Wengel J
Center for Synthetic Bioorganic Chemistry, Department of Chemistry, University of Copenhagen, Universitetsparken 5, DK-2100 Copenhagen, Denmark.
J Org Chem. 2001 Aug 10;66(16):5498-503. doi: 10.1021/jo015664l.
The novel bicyclic nucleoside (1S,5S,6S)-6-hydroxy-5-hydroxymethyl-1-(uracil-1-yl)-3,8-dioxabicyclo[3.2.1]octane [2'-deoxy-1'-C,4'-C-(2-oxapropano)uridine] (15), expected to be restricted into an O4'-endo furanose conformation, was synthesized from the known 1-(3'-deoxy-beta-D-psicofuranosyl)uracil 5. The phosphoramidite derivative of 15 was successfully incorporated into oligodeoxynucleotides using standard methods, and thermal denaturation studies showed moderate decreases in duplex stabilities of -2.1 and -1.5 degrees C per modification toward complementary DNA and RNA, respectively.
新型双环核苷（1S,5S,6S）-6-羟基-5-羟甲基-1-（尿嘧啶-1-基）-3,8-二氧杂双环[3.2.1]辛烷[2'-脱氧-1'-C,4'-C-（2-氧杂丙烷）尿苷]（15），预计会受限形成O4'-内型呋喃糖构象，它是由已知的1-（3'-脱氧-β-D-异呋喃核糖基）尿嘧啶5合成的。使用标准方法成功地将15的亚磷酰胺衍生物掺入寡脱氧核苷酸中，热变性研究表明，每次修饰对互补DNA和RNA的双链体稳定性分别适度降低-2.1和-1.5℃。
