Synthesis of a new type of artificial nucleic acid derived from optically active serine.
This paper describes the synthesis of a new type of nucleic acid analog derived from L-serine with ester linkages. The monomer unit bearing thymine base was synthesized from L-serine ethyl ester by a three-step reaction in good yield without racemization. 3-Nitro-1,2,4-triazol-1-yl-tris(pyrrolidin-1-yl)phosphonium hexafluorophosphate (PyNTP) was found to be highly effective for the rapid ester bond formation without racemization. 2-Phenyl-2-(trimethylsilyl)ethyl group was successfully employed as a carboxyl protecting group in solution-phase synthesis.
Wada
T
T
Department of Integrated Biosciences, Graduate School of Frontier Sciences, University of Tokyo, FSB-702, Kashiwanoha 5-1-5, Kashiwa 277-8562, Japan.
Tsuneyama
T
T
Saigo
K
K
D004247:DNA / Q000138:chemical synthesis* / Q000737:chemistry; D019281:Dimerization; D004952:Esters / Q000737:chemistry; D020135:Peptide Nucleic Acids / Q000737:chemistry; D012694:Serine / Q000737:chemistry*
D004952:Esters; D020135:Peptide Nucleic Acids; D012694:Serine; D004247:DNA