A-AcetoxyNPy

The hydrolysis of these model precursors was studied at 37 , with catalysis by hog liver esterase. The major product, isolated in 60-70% yield from the hydrolysis of a-acetoxyNPy, was 2-hyd oxy-tetrahydrofuran. This compound was identified by comparison to a reference sample,prepared by lead tetraacetate oxidation of 1,2,5-pentanetriol (53). Additional evidence was obtained by lithium aluminum hydride reduction of the product to 1,4-butanediol. Minor amounts of butenals were also identified as products of the hydrolysis of a-acetoxy IPy. 

In either case, these electrophilic intermediates should be capable of reaction with nucleophilic cellular constituents. The interactions of NPy and a-acetoxyNPy with guanosine and polyguanylic acid are currently being investigated. 

Figure 9. Mutagenicity of a-acetoxyNPy and 4-(N-carbethoxy-N-nitrosamino)-butanal in S. typhimurium TA1535...

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