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. Author manuscript; available in PMC: 2014 Mar 13.
Published in final edited form as: Chem Rev. 2012 Dec 3;113(3):2182–2204. doi: 10.1021/cr300169a

Figure 8. Proposed Binding Modes Leading to Either Trans or Cis Double Bonds.

Figure 8

Syn elimination of an (R)-3-hydroxyacyl-ACP (left) occurs by removal of the pro-2S hydrogen and results in a trans double bond. Syn elimination of an (S)-3-hydroxyacyl-S-ACP (right) by removal of the pro-2S hydrogen is expected to result in a cis double bond. In both cases, the hydroxyl group is held in place by interactions with tyrosine and aspartate residues. (The side chains shown are those found in DEBS DH.)