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Enzymatic reductions with dihydrogen via metal catalyzed cofactor regeneration

A cofactor, metal technology used in the field of enzymatic reduction with hydrogen through metal-catalyzed cofactor regeneration

Inactive Publication Date: 2002-06-05
EASTMAN CHEM CO
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In this field, for the low-cost and environmentally friendly H 2 There is an unmet need for simple yet efficient methods combining high selectivity as reducing agents and enzyme catalysis

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0112] Example 1 shows that in the presence of complexes containing ruthenium, TBADH and NADP + Under the conditions of the catalyst, H 2 Can be used to convert 2-butanone to 2-butanol. NADP + (28.0 mg, 36.6 μmol) was placed in 2 ml of 0.1 M phosphate buffer, and the pH value was adjusted to 8.1 with NaOH. To this solution was added TBADH (1.2 mg, 8.8 units) and placed in an 80 ml Fisher-Porter bottle. Evacuate the Fisher-Porter bottle and refill it with argon three times, then add [Cl 2 Ru(TPPTS) 2 ] 2 (6.4 mg, 5.0 μmol) and 2-butanone (5 μl). Evacuate the Fisher-Porter bottle and fill with 70psi of H 2 , and then heated to 40°C for two hours. The gas was released from the bottle, and GLC analysis of a liquid sample indicated the production of 9.5 μmol of 2-butanol.

Embodiment 2

[0117]Example 2 shows that in complexes containing ruthenium, TBADH and NADP + In the presence of catalyst, H 2 2-Heptanone can be converted to 2-heptanol with remarkable symmetric isomerism.

[0118] Under argon flow, fill 20ml of 0.1M phosphate buffer (pH7.0), 2-heptanone (100μl, 718μmol), TPPTS (74mg, 130.7μmol), NADP + (10 mg, 13.1 μmol) and TBADH (2.7 mg, 19.8 units). Finally add the ruthenium catalyst [Cl 2 Ru(TPPTS) 2 ] 2 (17mg, 6.5μmol) and sealed Fisher-Porter bottle, evacuated, filled with 70psiH 2 . Repeat the evacuation and filling of H twice 2 , and then heat the above apparatus to 60°C with an oil bath. GC analysis of a trace sample taken by the liquid sampler described above after 10 hours indicated the production of 227.8 μmol of 2-heptanol. An additional 13.0 μmol (240.8 μmol) had accumulated after 4 hours. The pressure was released from the above bottle and 2-heptanol was 70.5% (S) and 29.5% (R) (41.0% ee) by chiral GC. Cycle number of catalyst co...

Embodiment 3

[0120] Example 3 shows that the ruthenium catalyst [Cl 2 Ru(TPPTS) 2 ] 2 is through H 2 Restore NAD(P) + catalyst precursors.

[0121] NADP + (36.0mg, 47.0μmol) was placed in 2ml of 0.1M phosphate buffer. The pH of the solution was adjusted to 8.3 with NaOH and placed in an 80 ml Fisher-Porter bottle. Evacuate the Fisher-Porter bottle and refill it with argon three times, then add [Cl 2 Ru(TPPTS) 2 ] 2 (9.7 mg, 3.7 μmol). Evacuate the Fisher-Porter bottle and fill with 70psi of H 2 , and then heated to 40°C for two hours. The volatile gases were removed under reduced pressure, and the sample was dissolved in D 2 O middle. Add 20 μl of trimethylsilyl propionic acid standard solution to the above sample. 1 H NMR integration indicated that 29.0 μmol of NADPH was produced under these conditions. NADP + 1 H(D 2 O): δ9.35(s)N 2 , 9.17(d, 0.6Hz)N 6 , 8.84(d,1.0)N 4 , 8.42(s)A 2 , 8.21(t, 0.7)

[0122] N 5 , 8.11(s)A 8 , 6.10(d, 5.2Hz)N 1’ , 6.02(d,)A 1...

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PUM

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Abstract

The invention provides a process for reducing an unsaturated organic compound, comprising mixing the unsaturated organic compound and H2 in the presence of a catalyst to form a reduced organic product, wherein the catalyst comprises: a) at least one metal salt or complex, b) at least one nicotinamide cofactor; and c) a nicotinamide cofactor dependent enzyme, wherein: i) when the metal salt or complex is a platinum carbonyl cluster complex, the catalyst does not comprise a redox active dye; and ii) when the metal salt or complex is a rhodium phosphine complex, the nicotinamide cofactor dependent enzyme is not a mixture of horse liver alcohol dehydrogenase and lactate dehydrogenase.

Description

[0001] Cross References to Related Applications [0002] This application claims priority to US Provisional Patent Application Serial No. 60 / 123,833, filed March 11, 1999, which is hereby incorporated by reference in its entirety. field of invention [0003] The present invention generally relates to the use of H in the presence of a catalyst comprising a metal salt or complex, a nicotinamide cofactor; and an enzyme dependent on the nicotinamide cofactor 2 Process as a reducing agent for unsaturated organic compounds to form reduced organic products. Background of the invention [0004] The present invention relates to the use of H in the presence of an enzyme-containing catalyst 2 Catalytic methods for the reduction of organic compounds as reducing agents. Many artificial catalysts are known for reduction and / or hydrogenation reactions, but known catalysts are limited in their ability to selectively reduce or hydrogenate one un...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C12N9/02C12P1/00C12P7/02C12P19/36C12P21/00
CPCC12P7/02C12P21/00C12P1/00C12P19/36C12N9/0004
Inventor R·T·赫姆布雷P·S·瓦根克内希特J·M·彭尼
Owner EASTMAN CHEM CO