Nucleoside–boron cluster conjugates – Beyond pyrimidine nucleosides and carboranes

General methods for the synthesis of new purine and pyrimidine nucleosides modified with borane clusters and metallacarborane complexes are presented. They include: (1) attachment of carborane modification at 2′ position of nucleoside via formacetal linkage formation, (2) tethering of the metallacarborane group at nucleobase part of the nucleoside via dioxane ring opening in oxonium metallacarborane, carborane or dodecaborate derivatives, and (3) ‘‘click” chemistry approach based on Huisgen 1,3-dipolar cycloaddition. Proposed methodologies extend the range of nucleoside–boron cluster conjugates available and open new areas for their applications.

Graphical abstractProposed methodologies help to bypass limitations in the synthesis of nucleoside–boron cluster conjugates expanding the range of available derivatives and make possible study of broad spectrum of new pyrimidine as well as purine nucleoside conjugates in search for biological activities and technical applications.Figure optionsDownload full-size imageDownload as PowerPoint slide