Table 2.

Reduction of nitroolefins 1-5 by PETN reductase under biphasic reaction conditions^[a]

Number	Substrate	λmax[b] [nm]	Time[c] [days]	Conversion[d],[e] [%]	Yield[d],[e] [%]	Product[f]	ee[e] [%]
1		264	2	100	>99	6	N/A
(E)-2		319	2	100[g]	>99[g]	7	N/A
(E)-3		357	1	100	82	8	N/A
(E)-4a		306	3	100[h]	58[h]	(S)-9a	89[h]
(Z)-4a		208	3	100[h]	89[h]	(S)-9a	96[h]
(E)-4b		312	3	100	86	(S)-9b	63
(E)-4c		310	7	70	18	(S)-9c	72
(Z)-4c		221	4	100	91	(S)-9c	96
(E)-4d		314	7	73	35	(S)-9d	75
(Z)-4d		224	7	83	76	(S)-9d	>99
(E)-5a		316	3	100[h]	93[h]	(R)-10a	14[h]
(E)-5b		321	7	93	84	(R)-10b	54
(Z)-5b		230	7	88	80	(R)-10b	60

^[a]Conditions: The reactions contained potassium phosphate buffer (50 mM KH₂PO₄/K₂HPO₄ pH 7.0, 9.2 mL) nitroalkene (1.7 mM in 4.8 mL anaerobic isooctane), NADP⁺ (20 μM), glucose 6-phosphate (14-20 mM), glucose 6-phosphate dehydrogenase (10 units), deoxygenated PETN reductase (2 μM) and sec-butylbenzene (25 μL). Reactions were agitated at 200 rpm for 1-7 days at 30°C in an anaerobic cabinet. N/A=not applicable.

^[b]Maximal absorbance wavelength of the substrate used to monitor reduction.

^[c]Time of biphasic reaction in days.

^[d]Conversions and yields were determined by HPLC from calibration curve of each standard substrate and products and corrected using sec -butylbenzene as internal standard.

^[e]Chiralcel OD-H.

^[f]Absolute configuration assigned by comparison with literature data.[15]

^[g]Phenomenex C-18.

^[h]Chiralcel OJ.