Benzene-glycol nucleic acid-DNA chimeras form thermally and thermodynamically stable duplexes with complementary RNAs, and have base-discriminating abilities. This unit describes the synthesis of four nucleoside analogs, an adenine, cytosine, thymine, and guanine analogs with base-benzene-glycol structure. The synthesis starts with conversion of (S)-mandelic acid in arylboronic acid derivative, common intermediate. Nucleobase coupling of the intermediate and phosphitylation afford to phosphoroamidite units. © 2017 by John Wiley & Sons, Inc.

Abstract:In this study, we report the synthesis of benzeneglycol nucleic acids and studies of their biophysical and biological properties. Using (S)-mandelic acid as the starting material, we prepared phosphoramidite units for the synthesis of benzene-glycol nucleic acids. The benzene-glycol moieties effectively replace the sugar groups ordinarily found in DNA and RNA monomers. Oligonucleotides (ONs) containing these nucleoside

This paper describes the synthesis and properties of benzene-glycol nucleic acid (BGNA)–DNA chimeras containing four nucleoside analogs – thymidine, cytidine, adenosine, and guanosine – with a base-benzene-glycol structure.

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An Efficient Synthetic Method of Aliphatic Selenoamides via Selenoketene Intermediates.-Selenoamides are efficiently synthesized by treatment of terminal acetylenes or the bromopropene (XIII) according to A) followed by trapping the resulting selenoketene intermediate with amines. -(MURAI, T.; EZAKA, T.; NIWA, N.; KANDA, T.; KATO, S.; Synlett (1996) 9, 865-866; Dep. Chem., Fac. Eng., Gifu Univ., Yanagido, Gifu 501-11, Japan; EN)