Artificial nucleosides possessing metal binding sites at the 3'- and 5'-positions of the deoxyribose moieties.
This paper describes a convenient synthetic procedure for nucleoside mimics, 1-6, in which the 3',5'-hydroxy groups of natural 2'-deoxythymidine or 2'-deoxyadenosine are replaced by thiol, amine, or alkylthiol groups. Such nucleosides would be built up into a single DNA strand with cooperative participation of metal coordination, where internucleoside linkages are replaced by metal complexation motifs. The X-ray crystal structure and complexation behaviors of 3',5'-dithiothymidine, 1, with Au(I) are also reported.
Chiba
Jun-Ya
JY
Department of Chemistry, Graduate School of Science, The University of Tokyo, Hongo, Bunkyo-ku, Japan.
Tanaka
Kentaro
K
Ohshiro
Yukinori
Y
Miyake
Ryosuke
R
Hiraoka
Shuichi
S
Shiro
Motoo
M
Shionoya
Mitsuhiko
M
D000475:Alkenes / Q000737:chemistry; D000588:Amines / Q000737:chemistry; D018360:Crystallography, X-Ray; D004247:DNA; D006046:Gold; D008958:Models, Molecular; D018716:Molecular Mimicry; D015394:Molecular Structure; D009690:Nucleic Acid Conformation; D009705:Nucleosides / Q000138:chemical synthesis*; D013329:Structure-Activity Relationship; D013438:Sulfhydryl Compounds / Q000737:chemistry
D000475:Alkenes; D000588:Amines; D009705:Nucleosides; D013438:Sulfhydryl Compounds; D006046:Gold; D004247:DNA