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Fig. S1. Location of cysteine and methionine residues in PETN reductase. The protein is shown as a cartoon, with a gradient from blue at the N-terminus to red at the C-terminus. The active site FMN is shown as atom coloured sticks with yellow carbons. The cysteine and methionine residues are shown as red and green spheres, respectively.

Fig. S2. Accurate mass determination of nontreated and pretreated PETN reductase samples by ESI MS. Samples were analysed after undergoing the following pretreatments: (A) no treatment; (B) aerobic; (C) aerobic/NADH; (D) anaerobic; (E) anaerobic/NADH. All pretreatments were performed for 24 h at 25 °C. Further details can be found in 'Experimental procedures'. A molecular mass of 40 455 Da is consistent with PETN reductase in the absence of FMN and its N-terminal methionine.

Table S1. Effect of buffer type on the reduction of (E)-2-phenyl-1-nitroprop-1-ene (PNE) by wild-type PETN reductase under aerobic and anaerobic conditions.

Table S2. Effect of pH on the reduction of (E)-PNE by wild-type PETN reductase under aerobic and anaerobic conditions.

Table S3. Effect of pH and cofactor on the aerobic reduction of (E)-PNE by wild-type PETN reductase.

Table S4. Influence of enzyme concentration and buffer on the aerobic reduction of (E)-PNE by wild-type PETN reductase.

Table S5. Effect of enzyme concentration on the reduction of (E)-PNE by wild-type PETN reductase under anaerobic conditions.

Table S6. Effect of time on the reduction of (E)-PNE by wild-type PETN reductase under anaerobic conditions.

Table S7. Time course of reduction of (E)-PNE by wild-type PETN reductase under aerobic conditions.

Table S8. Effect of enzyme concentration on the reduction of (E)-PNE by wild-type PETN reductase under anaerobic conditions.

Table S9. Control reactions to evaluate the degree of isomerization of (E)-PNE to (Z)-PNE under biotransformation conditions.

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