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   Hydrogen-bond stabilization in oxyanion holes

How best to stabilise oxyanions with hydrogen bonds? The usual diagram for this shows a flat structure. Enzymes, however, prefer to place the hydrogen bonds at ninety degrees to this orientation.
Hydrogen-bond stabilization in oxyanion holes: grand jete to three dimensions
L. Simon and J. M. Goodman Org. Biomol. Chem. 2012, 10, 1905-1913.
DOI: 10.1039/C2OB06717J

Enzyme Catalysis by Hydrogen Bonds: The Balance between Transition State Binding and Substrate Binding in Oxyanion Holes
L. Simon and J. M. Goodman J. Org. Chem 2010, 75, 1831-1840.
DOI: 10.1021/jo901503d

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