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Enzymatic reduction of hydrazones to hydrazines.

Country of Origin: Germany
Reference Number: TODE20180910002
Publication Date: 10 September 2018

Summary

A German university has developed a novel process for the synthesis of hydrazines, compounds for the synthesis of several pharmaceuticals and precursors of natural products. The invention is more efficient and less hazardous than current procedures. The university offers a license and a technical cooperation agreement to the pharmaceutical or chemical industry.

Description

Optically active hydrazine compounds are valuable intermediate compounds for the synthesis of several pharmaceuticals and precursors for natural products. A prominent example is D-(+)-1-Phenyl-2-hydrazinopropan (D-(+)-JB-516), which includes a chiral hydrazine and acts as inhibitor of monoaminooxidase in mice brain. A precursor towards synthesis of the natural compound Manzacidin C also contains a chiral hydrazine as structural motif.

So far, hydrazines are prepared usually via traditional chemical synthesis methods. But these methods have several disadvantages, like the risk of generating hydrogen cyanide in an acidic environment as well as only low product yields. Alternative reaction modes using triethylsilane need relatively harsh reaction conditions and long reaction times.
A German university now developed a novel process focusing on the enantioselective syntheses of chiral hydrazines. A new route is now described here with the usage of an imine reductase for the reduction of the C=N-double bond of hydrazones (I) to the corresponding hydrazines (II). Especially, in the present innovation, it was shown that imine reductases are valuable biocatalysts for the enantio­selective reduction of hydrazones and may therefore be used for synthesis of enantiomeric enriched or pure products (up to 99%).

In an improved method, S- and R-selective enzymes may be used to fabricate the product of need.

The university offers a license agreement to the pharmaceutical and chemical industry. In order to upscale the invention to an industrial level the university offers also a technical cooperation agreement.
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Advantages and Innovations

The innovation - compared to existing procedures - lies in the completely different synthesis approach using an enzymatically controlled process. With this procedure, the purely chemical method (use of extremely toxic cyanide compounds) can be completely dispensed with. In addition, the enzyme control also makes it possible to produce the target product almost chirally clean (99%) and without having to separate it from its optical counterpart.

Further advantages:
• Avoidance of toxic and expensive heavy metal catalysts
• Smooth reaction conditions of the process running at ambient temperature
• reduction of hazardness in the preparation of hydrazines

Stage Of Development

Field tested/evaluated

Stage Of Development Comment

proof of function

Requested partner

The university offers a license agreement to implement the new process. The companies addressed come primarily from the pharmaceutical industry. The process is also used in the chemical industry. Otherwise, the technology offer is also aimed at all those who need hydrazines as intermediate components for their pharmaceuticals.
Since the enzymatic implementation of the offered technology has so far only been demonstrated on a small scale, technological cooperation would make sense. The aim would be to bring the process to an industrial level.

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