title: Catabolic conversion of sepiapterin to 6-(1-carboxyethoxy)pterin by Bacillus subtilis.
abstract: Structural elucidation of an intensely blue fluorescent compound (A) formed from sepiapterin by Bacillus subtilis is described. The structure of the catabolite (A) was found to be 2-amino-6-(1-carboxyethoxy)-4(3H)-pteridinone (9) from both spectroscopic and degradation studies. This was confirmed by an unambiguous synthesis of 9. The stereochemical structure of the side chain at the 6-position of A was confirmed to be the L(or S) configuration, as in sepiapterin, by analysis of the lactic acid formed from A on acid hydrolysis. This suggests that the side chain is rearranged intact during the catabolic conversion of sepiapterin. A possible mechanism for the conversion is discussed.
mesh_terms: D001412:Bacillus subtilis / Q000378:metabolism*; D055598:Chemical Phenomena; D002621:Chemistry; D008956:Models, Chemical; D011621:Pteridines / Q000378:metabolism*
chemical_list: C016219:2-amino-6-(1-carboxyethoxy)-4(3H)-pteridinone; D011621:Pteridines