Isolation and characterization of new pterins from nonmethanogenic archaebacteria

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Virginia Polytechnic Institute and State University

Several new pterins have been discovered in halophilic and thermoacidophilic archaebacteria. Two of these were identified in the extreme halophiles and were thus called halopterins. One of these halopterins is produced by Halobacterium salinarium, Halobacterium halobium, and Halococcus morrhuae and is called phosphohalopterin-1. It was given this name because it was the first halopterin discovered and it has four monophosphate esters per dimeric pterin. The proposed structure of phosphohalopterin-1 is as follows. [see document for diagram of chemical structure]

The other halopterin, which is produced by Halobacterium marismortui, Halobacterium volcanii, and Halobacterial strain GN-1, is called sulfohalopterin-2 because it has two sulfate esters per dimeric pterin and it was isolated and recognized after the isolation of phosphohalopterin-1. The proposed structure of sulfohalopterin-2 is as follows. [see document for diagram of chemical structure]

As shown above, both pterins are dimers with an ether linkage connecting the polyol side chains. Both of the halopterins are negatively charged because of the phosphate and sulfate esters on the side chains. In addition to the halopterins, a positively charged pterin has been isolated from Sulfolobus solfataricus. This pterin is very special since no positively charged unconjugated pterin had ever been found in nature before. This pterin is named solfapterin after the species name of the bacteria from which it was obtained. The structure of this pterin is still unknown but the preliminary data indicate that it is an unconjugated pterin with a polyol containing an amine on the side chain. Another positively charged pterin which is different from solfapterin was found in Thermoplasma. All of the above pterins are different from any previously described pterins and thus represent new pterins in the archaebacterial kingdom.

The discovery of these new pterins is important both to pterin biochemistry and to archaebacterial taxonomy. These discoveries also open up a new field, that is, the exploration of the function of these new pterins in norunethanogenic archaebacteria.