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. Author manuscript; available in PMC: 2009 Jun 23.
Published in final edited form as: J Am Chem Soc. 2008 Sep 23;130(41):13696–13708. doi: 10.1021/ja803928m

Scheme 1.

Scheme 1

Geometric and electrostatic changes in the (A) carbonyl C-O during peptide bond hydrolysis and (B) nonbridging oxygen atoms during phosphoryl transfer reactions (nucleophile not shown) going from the ground state (black) to the transition state (red).