374081-63-7Relevant articles and documents
Mechanistic studies in the synthesis of a series of thieno-expanded xanthosine and guanosine nucleosides
Zhang, Zhibo,Wauchope, Orrette R.,Seley-Radtke, Katherine L.
, p. 10791 - 10797 (2008/12/23)
During the synthetic pursuit of guanosine (tri-G) and xanthosine (tri-X) tricyclic nucleosides analogues, an interesting side product was discovered. In an effort to uncover the mechanistic factors leading to this result, a series of reaction conditions were investigated. It was found that by varying the conditions, the appearance of the side product could be controlled. In addition, the yield of the desired products could be manipulated to afford either a 50:50 mix of both tri-G and tri-X, or a majority of one or the other. To demonstrate the broad utility of the method, it was also adapted to the synthesis of guanosine and xanthosine from 5-amino-1-β-d-ribofuranosyl-4-imidazolecarboxyamide (AICAR). The mechanistic details surrounding the synthetic efforts are reported herein.
"Fleximers". Design and synthesis of a new class of novel shape-modified nucleosides(1).
Seley, Katherine L,Zhang, Liang,Hagos, Asmerom,Quirk, Stephen
, p. 3365 - 3373 (2007/10/03)
A new class of shape-modified nucleosides is introduced. These novel "fleximers" feature the purine ring systems of adenosine, inosine, and guanosine split into their individual imidazole and pyrimidine components (as in 1-3). This structural modification serves to introduce flexibility into the nucleoside while still retaining the elements essential for recognition. As a consequence, these novel fleximers should find use as bioprobes for investigating enzyme-coenzyme binding sites as well as nucleic acid and protein interactions. Their design and synthesis are described.
"Fleximers". Design and synthesis of two novel split nucleosides.
Seley,Zhang,Hagos
, p. 3209 - 3210 (2007/10/03)
[structure: see text] A new class of shape-modified nucleosides is introduced. The purine heterobases of adenosine and guanosine have been split into their imidazole and pyrimidine components, thereby introducing flexibility while retaining the elements n