Artificial DNAs with Metal Coordination Sites as Nucleobases.

Accession number;00A0163466
Title;Artificial DNAs with Metal Coordination Sites as Nucleobases.
Author; TANAKA KENTARO (Univ. of Tokyo, Grad. Sch.) CAO H (Graduate Univ. Advances Studies) TASAKA MOTOYUKI (Graduate Univ. Advances Studies) SHIONOYA MITSUHIKO (Univ. of Tokyo, Grad. Sch.)
Journal Title;Abstracts. Symposium on Biofunctional Chemistry
Journal Code:L0836A
ISSN:
VOL.14th;NO.;PAGE.12-13(1999)
Figure&Table&Reference;
Pub. Country;Japan
Language;Japanese
Abstract;We have recently reported the metal-assisted base pairing formed by artificial .BETA.-C-nucleosides having a phenylenediamine moiety as the metal chelating site. In this base pair, hydrogen bonding is replaced by metal coordination, thereby creating a novel binding motif in duplex DNA (Chart 1). This paper describes convenient syntheses of the other two types of artificial .BETA.-C-nucleosides possessing a metal chelating site (2-aminophenol and catechol) as the nucleobase moiety to control the net charges of metal-assisted base pairs (Figures 1 and 2). These nucleosides were synthesized via Friedel-Crafts coupling reactions as the key step between the aromatic ring and ribose moieties, whereas the nucleoside having a phenylenediamine moiety was prepared in rather longer steps through an RNA type intermediate followed by the removal of 2'-hydroxy group. (author abst.)