Science of Synthesis

Simon, R. C.; Busto, E.; Fischereder, E.-M.; Fuchs, C. S.; Pressnitz, D.; Richter, N.; Kroutil, W., Science of Synthesis: Biocatalysis in Organic Synthesis, (2015) 2, 411.

One of the most attractive routes to prepare amines is the catalytic amination of alcohols, because alcohols are often readily available, e.g. from renewable sources, on a large scale.[‌74‌] Moreover, ideally external reducing or oxidizing reagents may be avoided as both alcohol substrate and product amine are in the same oxidation state.[‌75‌] Even though no enzyme is capable of catalyzing the direct amination, various multienzyme one-pot cascades have been developed to afford the corresponding amines.

Mee eeeeeeee, e eeeee-eeee-eeeeeeeeee eeeeeeeeeee eeeeeee eee eeee eeeeeeee eeeee ee eee “eeeeeeeee eeeeeeee” eeeeeeee eee eee eeeeeeeee ee eeeeeee eeeeeeee eeeeeee eeeeeeeee eeeeeeee eeeee eeeeeeeeeee.[‌88‌] Me eee eeeee eeee, ee eeeeeee eeeeeeeeeeeee (MMM) eeeeeeeee eee eeeeeeeee ee eee eeeeeee eeeeeee ee eee eeeeeeeeeeeee eeeeeeee, eeeeee eee eeeeeeeeee ee eee eeeeeee eeeeeeee MMMM. Meee, eee ω-eeeeeeeeeeee eeeeeeee eee eeeeeeeee ee eee eeeeeeeeeeee eeeeeeee ee eee eeeeeee ee e-eeeeeee. Meeeeee, eeeeeee eeeeeeeeeeeee (MeeMM) eeeeeeee eee eeeeeeeee eee eeeeeeeee eeeeeeeee eeee ee eeeeeeeee MMMM eeeeeeee ee eee eeeeeeeee eee eee eeeeeeeeeeee ee e-eeeeeee eeee eeeeeeee. Meeeeee eeeeee eeeeeee eeeeeeeee ee eeee eeeeeee eeeeeeee eeeeeeee eee eeeeeeee eeee eeeeeeeee eeeeeeeeee eeee eee eeeeeeeeeeeee eeeeeeee (‌Meeee 8‌). Meee eeee eeeeeeeeeee ee eee eeeeeeeeeee ee eeee eeeeeeeeeee eeeeeee eee eee eeeeeeeeeee ee 8,ω-eeeee eeeee eeeeeeee eeeeeeeeeeeeeee eeeeee ee 8,ω-eeeeeeee, eeeeeeee eeeeeeee eeeeee eee eee eeeeeeeeeee ee eeeeeeeee eeeeeeeeeee (eeeeeee 8 eee 8). Me eeee eeeeeeeeee eeee, eee eeeeeeeee ee eeeeee-8,88-eeeeeee eee eeee eeeeeeeee ee e eeeeeeeeeee eeeee. Mee ee eee eeee eeeeeeeeee ee eee eeee, eee eeeeeeee ee 88% 8,8-eeeeeeeeeeeeeee ee eeeeeeee. Mee eeeeeee eeeeeee ee eeeeeeee ee eeee eeeee eeeeeee eeeeeeeee eeeeee ee eee eeeeeeeeeeee eeeeeeee ee eeee-eeeeeeeee eeeeeeee. Meeeeeeeeeeee, eee eeeeeeeeeeee eeeeeeee eee ee eeeeeeee eeeee ee eeeeeee, eee ee eeee eeee eee eeeeeeeeee ee eeeee eeeeeee ee ee eeeeeeeee ee eee eeeeeeee eeeee eeeeeeeeeee.[‌88‌]

‌Meeee 8‌ ω-Meeeeeeeeeee-Meeeeeeee Meeee-Meeeeee Meeeeee eee eee Meeeeeeee ee Meeeeee eee Meeeeeeee Meeeeeee[‌88‌,‌88‌,‌88‌]

Meeee	Meeeeeee Meeeeeee	MMMe	ω-Meeeeeeeeeeee	Meeeeee	Meeeeeeeee (%)	Meeee (%)	Mee
8		eM	MM		>88	–e	[‌88‌]
8		eM	MM		88	–e	[‌88‌]
8		eM	MM		>88	–e	[‌88‌]
8		eM	MM		>88	–e,e	[‌88‌]
8		eM	MM		88	88e	[‌88‌]
8		M	MM		88	88	[‌88‌]
8		MM	MM (M888M)		8	–e	[‌88‌]

e Meeeee ee eeeeeee eeeeeeeeeeeeee: eM = Meeeeeee eeeeeeeeeeeeeeeee; M = Meeeeeeeeee eeeee; MM = Meeeeeeee eeeeeeee.

e Meeeee ee ω-eeeeeeeeeeeee: MM = Meeeeeeeeeeeeee eeeeeeeee; MM = Meeeeeee eeeeeeeeee; MM (M888M) = Meeeeeeeee eeeeeeeeeeeee M888M eeeeeee.

e Mee eeeeeeee.

e 88% MMM eee eeeee eee ee eeeeeeeeee eeeeeee.

Mee eeeeeeeee ee eeeeeeeee eeeeeeee ee ee eeee eeee eeeeeeeeeee eeeeeeeeeeeeee eeeeeee ee eee eeeeeee eeeeeeeeeeeeeee eeeeee ee eeeeeeee α-eeeeee eeeeee. Me eeee eeeeeeeeee eeee, eee eeeeeeeeee ee eee eeeeeee ee eeeeee eeeeeee eee eeeeeeeeeeeeeee ee eee eeeeeeee eeeeeeee (eeeeeee), eee eeeee eeeeeee (eeeee), eee eeeeeeee eeeeeeeeee, ee eeee eee eeeeeeeeeeeeeeee ee eee MMM eee eee ω-eeeeeeeeeeee eeee ee eeeeeeeeee. Me eee eeeee eeee, eee eeeeeeeeeeee eeee eeee eeee eee eeeeeeeee ee eeeeeeeee eeeeeeee eeee eee ee ee eeeeeeeeee, eee ee eeeeeeeeeeeee eeeeeee, ee e eeeeeeeee eeeeeeee eeeeeeee ee eeee eeeeeeeee ee ‌Meeee 8‌. Mee eeeeeeee, eeeeeeee eeeeeee ee (M)-eeeee-8-eeeee (‌Meeee 8‌, eeeee 8) eee eeeeeeeee ee eee eeeeeeeeeeee ee (M)-eeeee-8-ee. Me eeee eeee, eee eeeee ee eeeeeeee ee eeeee eeeeeeeeeeee eeeeee (88%) eeeeeeee eeee eee eeeeeeee eeeeeee eeeeeeee ee eee eeeeeeeee ee eeeee-8-eee (>88% ee).[‌88‌] Meee eeeeeeeee ee eeeeeeeeeeee eeeeee ee eeeeeeeeee ee eee eeeeeeeeee eeee eee eeeeeee eeeeeeeee ee eee eeeeee. Mee eeeeeeeeeee ee eeeeee eeeeeeeee eeeeeeee eeee ee eeeeeeeeee eee eeee eeee eeeeeee, eeeeeee, ee eeee eeee eee eeeeeeeeeeeeee eeeee eee (8M,8M)-eeeeeeeeee eeeee eeeeeee (eeeee 8) eeee eeee 8% eeeeeeeeee.[‌88‌]

Meeeeeeeeeee Meeeeeeee

Meeeee-8,88-eeeeeee (‌Meeee 8‌, Meeee 8); Meeeeee Meeeeeeee:[‌88‌]

Meeeee-8,88-eeee (888.8 ee, 8.8 eeee) eee eeeeeeeee ee MMM (8 eM, 88 eee%) ee e eeeee-eeeeeeee eeeee (88 eM), eeeeeeee ee eee eeeeeeee ee e eeee ee e-eeeeeee (888 ee, 8 eeee) ee M8M (8 eM) eee e eeee ee MM8Me (888 ee, 8 eeee) ee M8M (8.8 eM). Mee eM eee eeeeeeee ee 8.8 ee eeeeeeee ee 8 M ee MeMM (88 µM). MMM+ (88 ee, 88 µeee), eee MMM (8 ee, 8 µeee), eeee eeeeeeeee ee M8M (888 µM), eeeeeeeeee M8M (8.88 eM), MMM (8 eM, 8 M), ω-eeeeeeeeeeee MM (8 eM, 8 M), eee MeeMM (888 eM, 8 M) eeee eeeee. Meeee eee eeeeeee eee eeee eeeeee ee 88 °M eee 888 eee (eeeeeee eeeeee, Meeeee Meeeeee) eee 88 e, eee eeeeeee eee eeeeeeeee eeee eee eeeeeee eee eeeeeeee eeeeeee e eeee eeee eeeeee eeeeeeeee; eeeee: 888 ee (88%).

References