title: Heat-induced formation of alpha,beta-unsaturated nucleoside dialdehydes and their activity with adenosine deaminase.
abstract: Application of heat to aqueous solutions of nucleoside dialdehydes (periodate-oxidized nucleosides) affords the corresponding alpha,beta-unsaturated aldehydes. The reaction was first discovered during studies with adenosine deaminase and was initially investigated enzymatically until the nature of the chemical transformation was determined. A UV peak at 230-250 n, characteristic of the alpha,beta-unsaturated aldehyde group, was obtained by difference spectroscopy and affords a more practical means to study the reaction. Adenosine dialdehyde, obtained by periodate oxidation of adenosine, afforded the same product upon heating as obtained by periodate oxidation of 9-(5-deoxy-beta-D-erythro-ent-4-enofuranosyl)adenine. Further proof of identity was obtained by reduction of these compounds with sodium borohydride and comparison of the dialchols obtained to each other and to a known unsaturated dialcohol. Heating of nucleoside dialdehydes at any time is not recommended. The exact composition of nucleoside dialdehydes used in previous and current biological studies is open to question.
mesh_terms: D058892:Adenosine Deaminase Inhibitors; D000447:Aldehydes / Q000138:chemical synthesis* / Q000494:pharmacology; D000818:Animals; D002417:Cattle; D006358:Hot Temperature; D066298:In Vitro Techniques; D007700:Kinetics; D009700:Nucleoside Deaminases / Q000037:antagonists & inhibitors*; D009705:Nucleosides / Q000138:chemical synthesis* / Q000494:pharmacology
chemical_list: D058892:Adenosine Deaminase Inhibitors; D000447:Aldehydes; D009705:Nucleosides; D009700:Nucleoside Deaminases