Feet first: Carboxylic acids with a primary amino group in the farthest position from the carboxy group are specifically bound to an artificial cyclotransferase based on [18]crown-6. The amino group fits into the [18]crown-6 substrate-binding site to bring the carboxyl group close to the 2-ammonio-1,3,5-triazine reaction site for selective conversion into a lactam.
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Kunishima et al. (2006) studied this question.
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