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J Med Chem. 1980 Jul;23(7):795-8.

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.

PMID:
7401106
DOI:
10.1021/jm00181a017
[Indexed for MEDLINE]

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