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. Author manuscript; available in PMC: 2011 Jul 8.
Published in final edited form as: J Med Chem. 2010 Jul 8;53(13):4813–4829. doi: 10.1021/jm100086u

Scheme 4.

Scheme 4

Hydrogen-bonding interactions in the -d-Ala-d-Ala peptidoglycan-vancomycin host-guest complex (left) compared to the -d-Ala-d-Lac peptidoglycan-vancomycin host-guest complex (right). The loss of a key hydrogen bond, and its replacement by unfavorable non-bonding repulsive interactions, is indicated by the red-colored arrows in the -d-Ala-d-Lac depsipeptide complex.161