Biochemistry of Halogenated Aldehydes and Ketones
The susceptibility of a halogen situated at the α position of an aldehyde or ketone to nucleophilic displacement plays a central role in much of the biochemical behavior of these compounds. Examples to be reviewed in this chapter include the reaction of α-chloro- and α-bromoaldehydes with nucleic acid components and the use of α-halocarbonyl compounds as affinity labels. The presence of halogen also affects the chemistry of the neighboring carbonyl group, making the carbonyl carbon more electrophilic, an effect especially pronounced with α-fluorine substitution. This has been used to advantage in the design of several transition state analogue enzyme inhibitors, based on the ready formation of tetrahedral intermediates from such halogen-substituted analogues.
KeywordsJuvenile Hormone Chloral Hydrate Renin Inhibitor Cytosine Residue Methyl Ketone
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