A concise treatment of pterins: some recent synthetic and methodology aspects and their applications in molecular sensors

Abstract

A concise account of pterins in chemistry and biology and their applications in molecular sensors including their optical spectroscopic properties are described. Different natural, synthetic, biological and photophysical aspects are also discussed. Synthetic access to direct functionalised pterins and a recently reported new thiophene annulation technique are described for the synthesis of Form B of molybdenum cofactor. The receptor properties of fluorescent pterin molecules including selenopyrimidines which are rarely reported for their binding of anions and neutral molecules are also of major importance in this review. For such an old and still so young, unexplored pterin system on its power to be sensitive for physical studies especially the interaction with cations, anions and neutral molecules are fascinating and research in this area is relatively new and expected to increase fast. Pterin based receptors are for the first time put into a useful review for the advantage of those who want to explore pterin and modified pterin as chromogenic and fluorogenic sensors.

Naturally Occurring Lumazines

“…41,42 Additionally, 6-oxolumazine (13) was found to be a strong competitive inhibitor of the enzyme xanthine oxidase, which plays an important role in the catabolism of purines in some species, including humans. 43 Violapterin (10) is often found together with the corresponding pterin compound isoxanthopterin (16) during isolation from different species. 35−37 Additionally, 6-oxolumazine (13) was observed as a major metabolite following the addition of xanthopterin (5) to a culture of soil bacteria.…”

“…Parallel with these synthetic efforts, the discovery of natural pteridine compounds began in 1889, when Sir Frederick Hopkins reported the isolation of the yellow pigments xanthopterin ( 5 ) and leucopterin ( 6 ) from the wings of the common brimstone butterfly ( Gonepterix rhamni ) and the cabbage butterfly ( Pieris rapae ), respectively . The structures of pterins 5 and 6 were not confirmed until 1940; since then, much work has been directed toward the isolation of new natural pteridines and the investigation of their biological roles. − , Most naturally occurring pteridines belong to the pterin family, and some of these pterins possess important biological properties including antitumor, antimicrobial, and antiviral activity, as well as being cofactors in enzymatic reactions. , Thus far, reviews of the reactivity, synthesis, isolation, and bioactivity of pteridines have focused on natural pterins and their analogues rather than lumazines. − ,− …”

Bicyclic 6-6 Systems: Pteridines

“…The dedicated journal of that name includes some reviews of compound classes of interest to the non-clinical reader, including pterin function in bacteria 10 and the applications of pterins in molecular sensors. 11 Biological roles of pteridines have been briefly reviewed. 12…”