title: Chemical synthesis of hydroxymethylphosphonate alpha-DNA.
abstract: In this paper, we report the synthesis of hydroxymethylphosphonate alpha-DNAs and related compounds by use of the H-phosphonate method. These modified alpha-DNAs were designed to improve the inherent poor solubility of well-known methylphosphonate alpha-DNAs by introduction of a more hydrophilic hydroxymethylphosphonate function. The hybridization ability of hydroxymethylphosphonate alpha-DNAs was studied. We also report a novel strategy for the synthesis of alpha-thymidine by use of C1'-epimerization. The details of the neighboring effect of various 5'- and 3'-hydroxyl protective groups such as carbamoyl groups on the beta-->alpha conversion will be described.
authors.affiliation: Department of Life Science, Faculty of Bioscience and Biotechnology, Tokyo Institute of Technology, Nagatsuta, Midoriku, Yokohama 226, Japan.
authors.forename: Y
authors.initials: Y
authors.lastname: Sato
authors.forename: G
authors.initials: G
authors.lastname: Tateno
authors.forename: T
authors.initials: T
authors.lastname: Wada
authors.forename: K
authors.initials: K
authors.lastname: Seio
authors.forename: M
authors.initials: M
authors.lastname: Sekine
mesh_terms: D004247:DNA / Q000138:chemical synthesis* / Q000737:chemistry; D019175:DNA Methylation; D006900:Hydroxylation; D015394:Molecular Structure; D009693:Nucleic Acid Hybridization; D063065:Organophosphonates / Q000737:chemistry; D012995:Solubility; D013237:Stereoisomerism
chemical_list: D063065:Organophosphonates; D004247:DNA