Table 1 ScFDC1-containing whole-cell biotransformations of 1a–x: maximal conversions obtained under optimized conditions (100 mM sodium phosphate buffer pH 7.0, cells OD600 of ~1, 35 °C).
From: Exploring the substrate scope of ferulic acid decarboxylase (FDC1) from Saccharomyces cerevisiae
Substrate | t (h) | c* (%) | Eb** (kcal/mol) | LUMO (eV) | Planarity*** | |
|---|---|---|---|---|---|---|
cinnamic acid | 1a | 24 | >99 | −6.6 | 1.681 | 1 |
(E)-3-(2-bromophenyl)acrylic acid | 1b | 48 | 83[a] | −6.4 | 1.502 | 0 |
(E)-3-(3-bromophenyl)acrylic acid | 1c | 8 | >99 | −5.9 | 1.305 | 1 |
(E)-3-(4-bromophenyl)acrylic acid | 1d | 24 | >99 | −5.2 | 1.313 | 1 |
(E)-3-(2-methoxyphenyl)acrylic acid | 1e | 48 | 92[a] | −5.9 | 1.579 | 1 |
(E)-3-(3-methoxyphenyl)acrylic acid | 1f | 48 | >99 | −5.5 | 1.638 | 1 |
(E)-3-(4-methoxyphenyl)acrylic acid | 1g | 72 | >99 | −5.7 | 1.376 | 1 |
(E)-3-(2-(trifluoromethyl)phenyl)acrylic acid | 1h | 72 | 62[a] | −6.2 | 1.212 | 0 |
(E)-3-(3-(trifluoromethyl)phenyl)acrylic acid | 1i | 48 | 87[a] | −5.0 | 1.170 | 1 |
(E)-3-(4-(trifluoromethyl)phenyl)acrylic acid | 1j | 48 | 82[a] | −4.3 | 0.931 | 1 |
(2E,4E)-5-phenylpenta-2,4-dienoic acid | 1k | 48 | >99 | −4.4 | 0.957 | 1 |
(E)-5-phenylpent-2-enoic acid | 1l | 72 | <1 | −5.7[c] | 1.450 | 0 |
(E)-3-(naphthalen-2-yl)acrylic acid | 1m | 48 | >99 | −4.7 | 0.924 | 1 |
(E)-3-(quinolin-2-yl)acrylic acid | 1n | 8 | 39[b] | −2.5 | 0.701 | 0 |
(E)-3-(quinolin-4-yl)acrylic acid | 1o | 8 | 28[b] | −6.0 | 0.638 | 0 |
(E)-3-(benzofuran-2-yl)acrylic acid | 1p | 8 | >99 | −4.9 | 1.222 | 1 |
(E)-3-(benzofuran-3-yl)acrylic acid | 1q | 30 | 79[a] | −5.4 | 1.421 | 1 |
(E)-3-(5-chlorobenzofuran-2-yl)acrylic acid | 1r | 8 | >99 | −3.2 | 0.909 | 1 |
(E)-3-([1,1′-biphenyl]-4-yl)acrylic acid | 1s | 30 | 59[a] | −3.8 | 0.822 | 0 |
(E)-3-(4′-fluoro-[1,1′-biphenyl]-4-yl)acrylic acid | 1t | 48 | 70[a] | −3.7 | 0.775 | 0 |
(E)-3-(5-phenylthiophen-2-yl)acrylic acid | 1u | 72 | 85[a] | −3.2 | 0.654 | 0 |
(E)-3-(5-(4-bromophenyl)furan-2-yl)acrylic acid | 1v | 72 | <1 | −3.6[d] | 0.556 | 1 |
(E)-3-(2-phenylthiazol-4-yl)acrylic acid | 1w | 72 | <1 | −2.8[c] | 0.429 | 1 |
(E)-3-(10-methyl-10H-phenothiazin-2-yl)acrylic acid | 1x | 72 | <1 | −[e] | 1.059 | 0 |
