| 89% |
With D-glucose; NADP In aq. phosphate buffer; ethanol at 30℃; for 7h; enantioselective reaction; |
|
| 85.4% |
With D-glucose In phosphate buffer at 30℃; for 24h; |
|
| 82% |
With magnesium(II) perchlorate; 1,4-dihydronicotinoyl bearing (R)-<(η5-C5H5)Fe(CO)(PPh3)> at C-3 and N-substituted (S)-β-hydroxycarboxamide derived from valinol In acetonitrile at 20℃; for 8h; |
|
| 82% |
With magnesium(II) perchlorate; (R,S)-(-)-<(η5-C5H5)Fe(CO)(PPh3)>-1-methyl-5-(1-hydroxymethylisopropylcarbamoyl)-1,4-dihydronicotinoyl In acetonitrile at 20℃; for 8h; |
|
| 76% |
In water at 28℃; for 16h; wet Geotrichum sp. G38 mycelium; other α-oxo esters, enantioselectivity; |
|
| 76% |
In water at 28℃; for 16h; wet Geotrichum sp. G38 mycelium; |
|
| 76% |
With Saccharomyces cerevisiae at 30℃; for 2h; aq. buffer; optical yield given as %ee; enantioselective reaction; |
|
| 75% |
|
21 EXAMPLE 21
EXAMPLE 21 Ethyl phenylglyoxylate (1.6 mmol) was asymmetrically reduced in the same manner as in Example 6, except that DMF was used as the reaction medium, giving 0.25 g of ethyl (R)-(-)-2-hydroxy-2-phenylacetate, having specific rotation [α]D20 of 38.8° (cl. 00, CHCl3). The synthesis yield was 80% and the optical yield was 75% e.e. |
| 75% |
|
21 EXAMPLE 21
EXAMPLE 21 Ethyl phenylglyoxylate (1.6 mmol) was asymmetrically reduced in the same manner as in Example 6, except that DMF was used as the reaction medium, giving 0.25 g of ethyl (R)-(-)-2-hydroxy-2-phenylacetate, having specific rotation [α] [20/D ] of 38.8° (cl. 00, CHCl3). The synthesis yield was 80% and the optical yield was 75% e.e. |
| 66.6% |
With magnesium(II) perchlorate; chiral bis 1,4-dihydronicotinamide In chloroform; acetonitrile for 1h; Ambient temperature; |
|
| 3% |
With 10-butyl-1,5-dihydro-5-phenyl-3-(S)-α-methylbenzyl-5-deazaflavin (15b) In dichloromethane at 40℃; for 576h; |
|
|
(enzymatic reduction); |
|
|
With magnesium(II) perchlorate In dichloromethane |
|
|
With Saline; Bacillus sp. DSM 730; glycerol at 37℃; for 20h; Yield given; |
|
|
With Chlorella sorokiniana In various solvent(s) at 30℃; for 72h; photoautotrophic cultivation under light; |
|
|
With potassium phosphate buffer; Streptomyces thermocyaneoviolaceus α-keto ester reductase; NADPH In water at 37℃; for 2h; |
|
|
With [1-butylpyridinium][closo-CB11H12]; hydrogen; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl at 50℃; for 12h; |
|
|
With cerium(III) chloride; hydrogen In ethanol at 70℃; for 20h; |
|
|
With formate dehydrogenase; Bacteroides fragilis α-hydroxysteroid dehydrogenase; sodium formate In water; dimethyl sulfoxide at 20℃; |
|
|
With D-glucose; D-glucose dehydrogense; Pyrococcus furiosus alcohol dehydrogenase In dimethyl sulfoxide at 37℃; |
|
|
With glucose dehydrogenase; D-glucose; recombinant reductase CgKR2 from Candida glabrata; NADP; sodium carbonate at 30℃; aq. phosphate buffer; Enzymatic reaction; optical yield given as %ee; enantioselective reaction; |
|
|
With D-glucose; Bacillus subtilis glucose dehydrogenase; Candida glabrata keto ester reductase No. 1 In ethanol at 25℃; for 12h; aq. phosphate buffer; Enzymatic reaction; optical yield given as %ee; stereoselective reaction; |
|
| > 99 % ee |
With D-glucose; D-glucose dehydrogenase; β-nicotinamide adenine dinucleotide 2'-phosphate reduced tetra(cyclohexylammonium) salt; carbonyl reductase from Pichia pastoris GS115 In aq. phosphate buffer; dimethyl sulfoxide at 30℃; Enzymatic reaction; |
4.3 Ketone reduction catalyzed by the yeast carbonyl reductase PasCR
General procedure: The typical reaction procedure was as follows: d-glucose (18 g L-1), glucose dehydrogenase (2 g L-1), NADPH (0.5 g L-1), PasCR (0.5 g L-1), and substrate solution in DMSO (50 μL, 0.25 M) were mixed in 1 mL of phosphate buffer (100 mM, pH 6.5). The reaction mixture was shaken at 30 °C overnight and extracted by methyl tert-butyl ether (1 mL). The organic extract was dried over anhydrous sodium sulfate and subjected to chiral GC or HPLC to determine the conversion and enantiomeric excess. The absolute configurations of product alcohols were identified by comparing the chiral GC or HPLC data with those of the standard samples. A control experiment was performed under same conditions without addition of the enzyme PasCR and no reduction product was observed. |
| 98 % ee |
With D-glucose; Candida glabrata keto ester reductase1-wide-type; lyophilized powders of BmGDH; sodium carbonate In aq. phosphate buffer at 25℃; Enzymatic reaction; stereoselective reaction; |
|
| > 99 % ee |
With C52H89N2O17(1+)*CH3O3S(1-); hydrogen; acetic acid In n-heptane; toluene at 30℃; for 1h; Autoclave; enantioselective reaction; |
|
| 93.6 % ee |
With Kluyveromyces polysporus alcohol dehydrogenase S237G mutant; isopropyl alcohol; NADPH In aq. phosphate buffer at 30℃; Enzymatic reaction; enantioselective reaction; |
Bioconversion and determination of enantioselectivity
General procedure: Bioconversion was conducted with 20 mM 1a-10a,20 U·mL-1KpADH variants, 40 mM isopropanol in PBS buffer (pH 7.0,100 mM) in total volume of 2 mL at 30 °C and 180 rpm overnight. Then,1 mL of the reaction mixture was withdrawn and extracted with ethylacetate. The organic phase was isolated by centrifugation and driedover anhydrous MgSO4. The conversion rate and enantioselectivity ofthe products were analyzed as described in supporting information. |
| > 99 % ee |
With D-glucose; nicotinamide adenine dinucleotide phosphate; carbonyl reductase from Gluconobacter oxydans, W193L/C93I/I187L mutant; glucose dehydrogenase, E170K/Q252L mutant In aq. phosphate buffer; octanol at 30℃; Microbiological reaction; Enzymatic reaction; stereoselective reaction; |
|
| 91 % ee |
With [RhCl2(p-cymene)]2; potassium <i>tert</i>-butylate; hydrogen; C47H43FeNOP2 In toluene for 12h; Inert atmosphere; |
11 Example 11
Under the protection of nitrogen, place 1.5mg (0.0025mmol) [Ru(p-cymene)Cl2]2, (Rc, SP)-I-2 (0.0055mmol) prepared above and solvent toluene (1.5mL) in one 10mL After reacting for 30 minutes, add a solution of substrate ethyl benzoylformate (0.5mmol), potassium tert-butoxide (0.05mmol) and 1.5mL toluene. After hydrogen replacement 3 times, the reaction is maintained at atmospheric pressure After 12 hours, the reaction was terminated, concentrated, washed with water, and dried to obtain ethyl (R)-2-hydroxyphenylacetate with an enantiomeric excess of 91% ee. |
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