Nucleosides. VI. Synthesis and circular dichroism spectra of 5'-(9-adenyl)-2',5'-dideoxy-.beta.-D-ribofuranosylthymine and-adenine

Abstract

Nucleosides. VI. The Synthesis and Circular Dichroism Spectra of 5 '-(9-Adenyl)-2 ',5 '-dideoxy-/3-D-ribofuranosylthymine and -adenine Sir:In our previous study of 5'-substituted nucleoside analogs as potential antiviral agents1 it was noted that (1) (a) T.

Double-headed nucleosides: Synthesis and applications

“…Shen and co-workers [ 57 – 58 ] proposed the synthesis of the double-headed nucleosides 5′-(adenine-9-yl)-5′-deoxythymidine ( 79 ) and 5′-(adenine-9-yl)-2′,5′-dideoxyadenosine ( 81 ) from 2′-deoxy-5′- O -tosylthymidine/adenosine 78 and 80 , respectively. The 2′-deoxy-5′- O -tosyl nucleosides were reacted with the sodium salt of adenine in DMF to afford the double-headed nucleosides 79 and 81 , respectively ( Scheme 18 ) [ 57 – 58 ].…”

Synthesis and modelling of DNA junction and minor groove zipper motifs incorporating the double-headed nucleoside 5′(S)–C-(thymine-1-ylmethyl)thymidine

“…The second base has been positioned either directly on the ribofuranose on the 2 -position 7 or as a replacement of either the 3 -hydroxy group 7 or the 5 -hydroxy group. [8][9][10] In the present study, the additional nucleobase is positioned at the 5 -carbon through a methylene linker. Hence, the (S)-configured epimer of 5 -C-(thymine-1-ylmethyl)thymidine 3 was found by simple molecular modelling to give the most interesting opportunities, as the additional base of this double-headed nucleoside moiety will be positioned in the minor groove of nucleic acid duplexes and additional base-base interactions between complementary strands can be predicted.…”

Synthesis and antiviral activities of new acyclic and “double-headed” nucleoside analogues

“…There are relatively few publications on the synthesis of these so called "double-headed nucleosides" or "abbreviated nucleosides". Nelson Leonard and associates [22,23], and in a separate simultaneous effort, Shen and colleagues [24] at Merck provided the first syntheses and characterizations of such molecules. Since then a number of publications, a few of which are referenced here [25][26][27][28][29], have followed Leonard's and Shen's leads.…”