Pushing at the Boundaries of Pterin Chemistry

Abstract

Pterins are molecules of substantial interest as they occur in nature in a number of forms with quite distinct and often indispensable roles. Chemically, the synthesis of the principle pterin scaffold is comparably simple, while the insolubility of the pterin building block renders synthetic derivatization extremely difficult. When aiming at modeling naturally occurring pterins of extended chemical structure, this is a considerable problem. A notable set of strategies was developed in the course of the present study, which are able to overcome the lack of reactivity of the pterin backbone. These include a strategic choice regarding protection groups, uncommon chemical transformation, ball milling and combinations thereof. Some novel pterins with quite distinct substitution motifs were successfully synthesized and characterized by spectroscopic and spectrometric analyses as well as single-crystal structural analyses for three of them.

Keywords

• pterin
• tosylation
• Sonogashira cross-coupling
• Suzuki cross-coupling
• solid-state mechano-synthesis