Table 1.

Substrates of SMOs and related proteins.

Substrate	Enantioselectivity	Comment	Reference∗
Chiral epoxidation reactions
Styrene	(S)	Model substrate
Indene	(1S,2R)	Target for pharmaceutical industries as a precursor of indinavir	Hollmann et al., 2003; Lin et al., 2010
Styrene with substitutions at the aromatic ring	(S)	Activity often similar to the model substrate styrene
Styrene with substitutions at the vinyl chain	(S)	Mutations in the active site can change enantioselectivity in case of bulky substitutions	Lin et al., 2012; Toda et al., 2012a
Heterocyclic compounds	(S)	Formation of pyridine-like epoxides	Lin et al., 2010; Toda et al., 2012a
Non-conjugated alkenes including allylbenzenes	(S)	Much lower activity or rate of biotransformation compared to aromatic, conjugated substrates	Lin et al., 2010, 2011; Toda et al., 2012a,b, 2014
Indole	n.d.	Product not determined yet, but it auto-catalytically forms indigo in presence of molecular oxygen	Toda et al., 2012b; Sadauskas et al., 2017
Chiral sulfoxidation reactions
Aromatic sulfides (e.g., thioanisole) including derivatives with substitutions at the aromatic ring	(R), (S)	Thioanisole (methyl phenyl sulfide) is the model substrate Enantioselectivity depends on the type of enzyme selected	van Hellemond et al., 2007; Paul et al., 2015; Riedel et al., 2015

n.d., not determined. ^∗References have been summarized by Montersino et al. (2011), Huijbers et al. (2014), and Tischler (2015). Furthermore, a number of important reference are given in the table to clarify comments or more recent findings.