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. Author manuscript; available in PMC: 2018 Dec 14.
Published in final edited form as: Chembiochem. 2017 Nov 9;18(24):2380–2384. doi: 10.1002/cbic.201700397

Table 3.

Activities and diastereoselectivities of biocatalysts for the reaction of electron-deficient and aliphatic olefins with ethyl diazoacetate.a

graphic file with name nihms949502u2.jpg
catalyst substrate yield [%] TTNb drc,d (cis:trans)
heme 4 6 29 31:69
BM3h-T268A/heme 4 7 35 43:57
Ir(Me)-DPIX 4 8 40 14:86
WIVS-FM*-T268A/C400G/Ir(Me)-DPIX 4 29 147 13:87
heme 5 n.d.e n.d.e n.d.e
BM3h-T268A/heme 5 n.d.e n.d.e n.d.e
Ir(Me)-DPIX 5 5 23 30:70
WIVS-FM*-T268A/C400G/Ir(Me)-DPIX 5 11 55 26:74
WIVS-FM*-F87W/T268A/C400G/Ir(Me)-DPIX 5 19 95 26:74
a

reaction conditions: 100 mM olefin, 10 mM EDA, 20 μM catalyst, in 0.1 M NaPI pH 6.0 100 mM NaCl buffer, 5% DMF as cosolvent (reactions with heme and heme enzymes also contain 10 mM dithionite). TTN and diastereoselectivities determined by chiral GC analysis. Enantiomers could not be resolved by chiral GC.

b

TTN = total turnover number.

c

Diastereomer identity determined by comparison to authentic standards.

d

Enantioselectivities are reported in table S4 and S5.

e

n.d. = not detected.