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. Author manuscript; available in PMC: 2022 Apr 7.
Published in final edited form as: J Am Chem Soc. 2021 Mar 29;143(13):5011–5021. doi: 10.1021/jacs.0c13164

Table 1.

Reaction yields of 8-5' (c) and 8-8' (b) coupling products and enantiomeric excess of (+)-pinoresinol analogues (b)

monomers coupling oxidant plant extracta 8-5’ (μM)b [%]c 8-8’ (μM)b [%]c 8-8' regioisomeric
content (%)d 		% eee
1 CA-CA (2) TvLac EV 250 ± 47 [50] 122 ± 26 [24] 33 2
PhDIR 57 ± 10 [11] 446 ± 29 [89] 89 88
1 + 8 CA-MCA (17) TvLac EV 86 ± 11 [17] 33 ± 5 [7] 28 2
PhDIR 55 ± 2 [11] 83 ± 3 [17] 60 91
MCA-MCA (26) TvLac EV 62 ± 14 [12] 15 ± 5 [3] 19 0
PhDIR 41 ± 3 [8] 11 ± 2 [2] 21 31
1 + 10 CA-FMCA (19) TvLac EV 136 ± 19 [27] 24 ± 5 [5] 15 1
PhDIR 10 ± 2 [2] 145 ± 4 [29] 94 94
FMCA-FMCA (28) TvLac EV N/Af 49 ± 8 [10] N/Af −2
PhDIR N/Af 129 ± 3 [26] N/Af 82
1 + 11 CA-ECA (20) TvLac EV 182 ± 12 [36] <10g [<2] <5 0
PhDIR 54 ± 11 [11] 88 ± 16 [18] 62 89
ECA-ECA (29) TvLac EV 168 ± 11 [34] <10g [<2] <6 −1
PhDIR 147 ± 23 [29] 20 ± 10 [4] 12 47
a

plant extracts obtained with APW from leaves expressing empty vector (EV) or PhDIR.

b

Reaction yield was estimated from a standard curve using EIC peak integration as analyzed by LC-MS on C18 chromatography. For 17 and 26, standard curves of 2b and 2c were used to estimate yields. Error values are standard deviations of triplicates.

c

100% theoretical yield corresponds to 500 μM product generated from coupling of 500 μM each substrate (1mM total substrate concentration).

d

8-8' regioisomeric content was calculated by the following formula: [8-8', b]/([8-8', b]+[8-5', c])*100%.

e

ee: enantiomeric excess of (+)-pinoresinol or analogue over (−)-pinoresinol or analogue, calculated using the EIC peak integration ratios on chiral chromatography.

f

Not applicable; 8-5’ coupling product was not observed with the fluorine substituent.

g

Below limit of linearity of 10 μM.