Chemical synthesis of hydroxymethylphosphonate alpha-DNA.
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.
Sato
Y
Y
Department of Life Science, Faculty of Bioscience and Biotechnology, Tokyo Institute of Technology, Nagatsuta, Midoriku, Yokohama 226, Japan.
Tateno
G
G
Wada
T
T
Seio
K
K
Sekine
M
M
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
D063065:Organophosphonates; D004247:DNA