Biosynthesis of defensive allomones in leaf beetle larvae: stereochemistry of salicylalcohol oxidation in Phratora vitellinae and comparison of enzyme substrate and …

…, NJ Oldham, K Dettner, JM Pasteels, W Boland

Index: Veith; Oldham; Dettner; Pasteels; Boland Journal of Chemical Ecology, 1997 , vol. 23, # 2 p. 429 - 443

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Citation Number: 23

Abstract

Abstract (7 S)-[2 H 5]-Salicylalcohol (3) and (7 R)-[2 H 1]-salicylalcohol (5) have been synthesized in order to examine the stereospecificity of salicylalcohol oxidase from the defensive secretion of the salicylaldehyde-producing leaf beetle Phratora vitellinae. Oxidation was found to proceed by selective removal of the C (7)-HR hydrogen atom (Re- specificity) to yield salicylaldehyde.(7 S)-[2 H 6]-Benzylalcohol (9) was also oxidized Re- ...