Table 1.

Biocatalytic transmethylation of phenolic substrates mediated by EjOMT and variants.^[a]

Substrate	Z	R1	R2	R3	Best EjOMT variant	Conv. [%][b]
1  a, ferulic acid	CH=CHCOOH	OCH3	H	H	I133S/L138V/L342V	>99
2  a, coumaric acid	CH=CHCOOH	H	H	H	I133S/L138V/L342V	>99
3  a, sinapinic acid	CH=CHCOOH	OCH3	H	OCH3	I133S/L138V/L342V	97
4  a, caffeic acid	CH=CHCOOH	OH	H	H	I133S/L138V/L342V	>99
5  a, eugenol	CH2CH=CH2	OCH3	H	H	I133S/L138V/L342V	>99
6  a, isoeugenol	CH=CHCH3	OCH3	H	H	I133S/L138V/L342V	>99
7  a	CH2CH=CH2	OCH3	H	OCH3	I133S/L138V/L342V	96
8  a	CH2CH2CH3	H	H	H	I133S	>99
9  a	CH2CH2CH3	OCH3	H	H	I133S/L138V/L342V	>99
10  a, vanillyl alcohol	CH2OH	OCH3	H	H	I133S	>99
11  a, vanillin	CHO	OCH3	H	H	WT or I133S	>99
12  a	CHO	H	H	H	WT or I133S	74
13  a	CHO	OH	H	H	WT	43 (11b)
14  a	CHO	H	OH	H	–	–[c]
15  a, syringaldehyde	CHO	OCH3	H	OCH3	I133S/L138V/L342V	99
16  a	COOH	H	H	H	I133S/L138V/L342V	99
17  a	COOH	OH	H	H	I133S	99
18  a, vanillic acid	COOH	OCH3	H	H	I133S or I133S/L138V	99
19  a	COOH	H	OH	H	–	–[c]
20  a, syringic acid	COOH	OCH3	H	OCH3	I133S/L138V/L342V	46
21  a	CH2COOH	OH	H	H	WT	99
22  a	CH2COOH	OCH3	H	OCH3	I133S/L138V/L342V	32

[a] Reaction conditions: 1 mM substrate, 2 mM SAM and 1 mg mL⁻¹ purified EjOMT, 50 mM NaP_i buffer pH 7.4, 30 °C, 180 rpm, 18 h. [b] Determined by reverse‐phase HPLC. [c] No conversion.