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. Author manuscript; available in PMC: 2014 Jun 5.
Published in final edited form as: J Am Chem Soc. 2013 May 23;135(22):8153–8156. doi: 10.1021/ja403441x

Scheme 2.

Scheme 2

The reaction catalyzed by HppE (A) and the proposed mechanisms to account for the reactions of HppE with (R)-1-HPP (17) (B) and (1R,2R)- or (1R,2S)-2-amino-1-HPP (23 or 24) (C). Route a, carbocation rearrangement. Route b, radical-induced fragmentation/recombination.