Recent work has focused on the damaging effects of free radicals on biological molecules. This study investigates the kinetics of the attack of OH radicals Oil L-alanine ethyl ester in the gas phase in cold beams of Laval nozzle expansions. Experiments and high-level theory are used to understand the preferred site of attack by the OH radical. Optimizations of L-alanine and L-alanine ethyl ester show that the essential transition state features for hydrogen abstraction off the C-alpha, C-beta, and N are similar. The energetics show that for L-alanine, the C-alpha-site, C-beta-site, and N-site transition states are all below the reactants level. For L-alanine ethyl ester, however, the energetics for hydrogen abstraction off the C-alpha and N are the preferred site of reaction. These findings are Supported by the observed negative temperature dependence of the rate constants of OH with alanine ethyl ester in Laval nozzle expansion experiments. More importantly, both the experiments and theory show that L-alanine ethyl ester provides a good model For gas phase studies of the amino acids such as L-alanine.