Table 2.
Reductive amination of aromatic ketones catalyzed by LE‐AmDH variants.[a]
|
% Analytical yields of amine and (ee) [b] | |||||
|---|---|---|---|---|---|
|
Sub. |
v1[c] |
v22 |
v24 |
v25 |
v27 |
|
10 b |
n.d. (n.m.) |
n.d. (n.m.) |
n.d. (n.m.) |
n.d. (n.m.) |
n.d. (n.m.) |
|
11 b |
>99 (>99) |
97 (>99) |
50 (>99) |
84 (>99) |
34 (>99) |
|
12 b |
74 (>99) |
76 (>99) |
11 (>99) |
62 (>99) |
11 (>99) |
|
13 b |
86 (89) |
52 (89) |
3 (n.m.) |
32 (>99) |
1 (n.m.) |
|
14 b |
76 (97) |
83 (>99) |
n.d. (n.m.) |
53 (>99) |
n.d. (n.m.) |
|
15 b |
87 (>99) |
93 (>99) |
8 (n.m.) |
53 (>99) |
n.d. (n.m.) |
|
16 b |
10[d] (n.m.) |
13 (n.m.) |
n.d. (n.m.) |
10 (n.m.) |
n.d. (n.m.) |
|
17 b |
n.d. (n.m.) |
n.d. (n.m.) |
n.d. (n.m.) |
5 (n.m.) |
1 (n.m.) |
|
18 b |
99 (>99) |
97 (>99) |
50 (>99) |
84 (>99) |
34 (>99) |
|
19 b |
86. (n.a.) |
85 (n.a.) |
5 (n.a.) |
75 (n.a.) |
7 (n.a.) |
|
20 b |
79 (>99) |
80 (>99) |
9 (>99) |
64 (>99) |
12 (>99) |
|
21 b |
82 (>99) |
99 (>99) |
41 (>99) |
85 (>99) |
27 (>99) |
[a] Experimental conditions: 0.5 mL final volume in Eppendorf tubes; buffer: ammonium formate (2 m, pH 9.0); T: 50 °C; reaction time: 48 h; agitation orbital shaker (170 rpm); [substrate]: 10 mm; [NAD+]: 1 mm; [LE‐AmDH variant]: 90 μm; [Cb‐FDH]: 16 μm. NC 1: reaction without LysEDH or LE‐AmDH variant; NC 2: reaction without any enzyme addition (LysEDH or LE‐AmDH, and FDH). In all cases, NC1 and NC2 resulted in no detectable analytical yields for amines and alcohols. [b] Numbers in parentheses indicate the ee (%) of the amines formed. n.d.: not detected; n.m.: ee not measured due to too low conversion; n.a.: not applicable (non‐chiral product). [c] Data reported for reductive amination catalyzed by LE‐AmDH‐v1 are from Ref. [15k]. [d] The reaction was run at 30 °C.