Hydrogen-bond recognition of cyclic dipeptides in water

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C. Allott, H. Adams, Christopher A. Hunter, James A. Thomas, Pablo L. Bernad Jr. and Carmen Rotger


Abstract

An amide macrocycle with a highly preorganised cavity containing both polar and non-polar recognition sites forms stable complexes with cyclic dipeptides in water via amide–amide hydrogen-bonds, NH–π hydrogen-bonds and hydrophobic contacts.


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