3601-90-9Relevant articles and documents
Synthesis and DNA incorporation of an ethynyl-bridged cytosine C-nucleoside as guanosine surrogate
Heinrich, Daniel,Wagner, Thomas,Diederichsen, Ulf
, p. 5311 - 5314 (2008/09/17)
(Chemical Equation Presented) As a guanosine mimic that lacks the preference for syn or anti conformation a cytosine C-nucleoside was synthesized connecting the nucleobase at the anomeric center by an ethynyl linker. The key step was a Sonogashira cross coupling of 5-iodocytosine with 1′-ethynyl-2′-deoxyribose. The new C-nucleoside incorporated into G/C-alternating oligonucleotides emerged as guanosine substitute, however, with reduced duplex stability. B-Form DNA was strongly stabilized by the new surrogate even in typically Z-DNA forming sequences and in Z-form inducing environment.
Steric fixation of bromovinyluracil: Synthesis of furo[2,3-d]pyrimidine nucleosides
Eger,Jalalian,Schmidt
, p. 211 - 218 (2007/10/02)
A new synthetic proccdure for the preparation of 5,6-dihydrofuro[2,3-d]pyrimidin-2(3H)-one (3) and its deoxyriboside 8 is reported. Compound 3 undergoes nucleophilic reactions with various agents to yield 5-substituted uracil derivatives. The dehydro derivative of 3, furo[2,3-d]pyrimidin-2(3H)-one (18) was synthesized by cyclization of BVU 15, which made us develop a reproducible and high yield method for the synthesis of BV(D)U. Starting from 18, the α-deoxyriboside 20 and the β-riboside 22 were prepared.