Lyase and DNA Encoding the Lyase, Vectors Containing DNA, and Methods for Asymmetric Synthesis of (S)-Phenylacetylcarbinol

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This patent describes a genetically engineered lyase enzyme and the corresponding DNA which codes for it, as well as vectors containing this DNA. The main innovation is a modified form of the enzyme ApPDC-E469G (from Acetobacter pasteurianus), where the amino acid tryptophan at position 543 is replaced with a less bulky amino acid. This engineered enzyme is used in a process for the highly enantioselective (asymmetric) synthesis of (S)-phenylacetylcarbinol (S-PAC) from inexpensive, non-chiral starting materials such as benzaldehyde and pyruvate or acetaldehyde, achieving very high enantiomeric excess (up to 97%).

Use CasesContent extracted from patent full text and abstract with AI.

• Production of (S)-phenylacetylcarbinol for use as a chiral building block in pharmaceutical manufacturing, especially for drugs like ephedrine and pseudoephedrine.
• Synthesis of fine chemicals where high-purity (S)-phenylacetylcarbinol is required.
• Industrial biocatalytic processes replacing less selective chemical methods for making chiral intermediate compounds.
• Biotechnology applications involving engineered microorganisms for efficient chiral compound synthesis.

BenefitsContent extracted from patent full text and abstract with AI.

• Achieves very high enantiomeric excess of (S)-phenylacetylcarbinol (up to 97% ee), reducing or eliminating the need for costly purification/separation of enantiomers.
• Utilizes inexpensive, non-chiral starting materials, making the process more cost-effective and scalable.
• The engineered enzyme produces little to no by-products or regioisomers, simplifying downstream processing.
• Can be used with isolated enzyme, cell extracts, or whole cells, offering flexibility in bioprocess approaches.
• Enables more sustainable and environmentally friendly synthesis routes compared to traditional chemical methods.

Technical Classifications (CPCs)

Inventors & Applicants

Patent Abstract

The invention relates to a lyase and a lyase-encoding DNA, to vectors containing the DNA and to a method for the asymmetric synthesis of (S)-phenylacetylcarbinol. According to the invention, a lyase is provided, in which tryptophan is replaced with an amino acid at position 543 in protein ApPDC-E469G, said protein being modified with respect to the wild type of Aceobacter pasteurianus, or in which it is less space-filling than tryptophan. According to the invention, deoxyribonucleic acids are furthermore provided, which encode the lyase. (S)-phenylacetylcarbinol can be produced with the lyase according to the invention from the educts benzaldehyde and pyruvate or acetaldehyde with an enantiomeric excess of at least 94 %.