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  1. Spectroscopy
  2. US20080314835A1 - Chiral separating agents with active support - Google Patents
  3. EPB1 - Method for producing optically active amines - Google Patents

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Resolution of Racemic Bases

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The fUr of the address was however made with a tomb of five circumstances, and shortly made in Egyptians. The recombinant expression vectors of the invention can be designed for expression of catalytic enzyme proteins in prokaryotic or eukaryotic cells. For example, polypeptides of the invention can be expressed in bacteria e. Alternatively, the recombinant expression vector s can be transcribed and translated in vitro, for example using T7 promoter regulatory sequences and T7 polymerase.

Expression of proteins in prokaryotes is most often carried out in E. Fusion vectors add a number of amino acids to a protein encoded therein, usually to the amino terminus of the recombinant protein. Such fusion vectors typically serve three purposes: 1 to increase expression of recombinant protein; 2 to increase the solubility of the recombinant protein; and 3 to aid in the purification of the recombinant protein by acting as a ligand in affinity purification. Often, a proteolytic cleavage site is introduced at the junction of the fusion moiety and the recombinant protein to enable separation of the recombinant protein from the fusion moiety subsequent to purification of the fusion protein.

Such enzymes, and their cognate recognition sequences, include Factor Xa, thrombin and enterokinase. To maximize recombinant protein expression in E. Another strategy is to alter the nucleic acid sequence of the nucleic acid to be inserted into an expression vector so that the individual codons for each amino acid are those preferentially utilized in E. Such alteration of nucleic acid sequences of the invention can be carried out by standard DNA synthesis techniques and is described in the Examples.

The catalytic enzyme expression vector can be a yeast expression vector, a vector for expression in insect cells, e.

Spectroscopy

When used in mammalian cells, the expression vector's control functions can be provided by viral regulatory elements. For example, commonly used promoters are derived from polyoma, Adenovirus 2, cytomegalovirus and Simian Virus In a preferred embodiment, the promoter is an inducible promoter, e. In a preferred embodiment, the isolated nucleic acid encodes a plurality of catalytic enzymes.

It would be understood that not all of the enzymes introduced into a host cell have to be heterologous; there may be a mixture of heterologous and non-heterologous enzymes depending on the cell type or strain used as host. In another preferred embodiment, said plurality of catalytic enzymes is arranged as at least one module selected from the group comprising:.

Another aspect the invention provides at least one expression construct comprising at least one nucleic acid sequence that is heterologous according to any aspect of the invention. Preferably the at least one construct comprises a plasmid suitable for expression of at least one catalytic enzyme in a bacterium. Another aspect the invention provides a host cell which includes at least one nucleic acid molecule described herein, e. Such terms refer not only to the particular subject cell but to the progeny or potential progeny of such a cell.

Because certain modifications may occur in succeeding generations due to either mutation or environmental influences, such progeny may not, in fact, be identical to the parent cell, but are still included within the scope of the term as used herein. A host cell can be any prokaryotic or eukaryotic cell. For example, at least one catalytic enzyme protein can be expressed in bacterial cells such as E. Other suitable host cells are known to those skilled in the art. One or more vector DNAs can be introduced into host cells via conventional transformation or transfection techniques.

Arrangements of such enzymes as modules allow flexibility in constructing a serial cascade of reactions in one pot. One or more modules may be engineered onto the same plasmid. For example, a host cell comprising the said first and third modules, on the same or separate plasmids, is capable of catalyzing the conversion of a terminal alkene to a 1,2-amino alcohol. The cells may contain a single expression vector or construct, such as a plasmid, which expresses a single catalytic enzyme or co-expresses a plurality of catalytic enzymes as described herein under the control of at least one regulatory element.

The catalytic enzymes may be arranged in the plasmid as an individual artificial operon under the control of a promoter with one ribosome-binding site before every gene, or arranged with individual promoters.


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Accordingly, a one-pot synthesis cascade may be achieved with cells expressing all required catalytic enzymes on one or several plasmids, or with different recombinant cells which each express a specific repertoire of catalytic enzymes, providing the necessary cells are included for a particular chemical transformation.

In a preferred embodiment, the cells are recombinant bacterial cells; more preferably E. In another preferred embodiment, said cells comprise at least one expression construct selected from the group comprising. In a preferred embodiment, in iii the lyase is a phenylalanine ammonia lyase PAL and the decarboxylase is a phenylacrylic acid decarboxylase PAD. A host cell of the invention can be used to produce i. Accordingly, the invention further provides methods for producing one or more catalytic enzyme proteins, e.

In another embodiment, the method further includes isolating one or more catalytic enzyme proteins from the medium or the host cell. To realize the targeted asymmetric alkene functionalizations, microbial cells containing two to three basic enzyme modules were designed, with each of them catalyzing two to four enzymatic reactions FIG. The basic modules were designed by using the following criteria: a each module utilizes a stable input, such as alkene, diol and hydroxy acid, and gives a stable output, such as diol, hydroxyl acid, amino alcohol and amino acid; b each module enables fast conversion of unstable or toxic intermediates, such as epoxide, hydroxy aldehyde and keto acid, to minimize their accumulation and side reactions.

Besides using alkenes as the starting material, the use of readily available amino acids is an attractive alternative as they are currently produced by fermentation in large amounts and at low cost. With that in mind, the one-pot biotransformation of biobased L-phenylalanine to valuable chiral compounds via cascade biocatalysis was achieved as an example FIG. Specifically, the biocatalytic cascade first involves the deamination-decarboxylation of L-phenylalanine S -1 to styrene S -3 by using phenylalanine ammonia lyase PAL and phenylacrylic acid decarboxylase PAD.

This is followed by the combination of the different enzyme modules for the functionalization of the alkenes to produce various chiral compounds S -5, R -5, S -6, S -7, S -8 and S All of these can be incorporated into a single E. Escherichia coli T7 expression cells were purchased from New England Biolabs. LB medium, tryptone, yeast extract, and agar were obtained from Biomed Diagnostics.

Chloramphenicol, streptomycin, ampicillin, kanamycin, and glucose were purchased from Sigma-Aldrich. The trace metal solution contains 8. Freshly prepared E. Then the mixture was centrifuged g for 10 min. The electrophoresis was run in a setup of Mini-Protean tetra cell at V for 15 min and V for 75 min. The figure was obtained with GS calibrated densitometer Bio-Rad , and quantification analysis was done with the volume tools in the Image Lab software Bio-Rad.

Escherichia coli T7 expression strain an E. ACS Catal. Ald gene was amplified from the genomic DNA extracted from B. Codon-optimized cv gene was synthesized from Genscript based on the sequence from C. Codon-optimized sco gene was synthesized from Genscript based on the sequence from S. Purification of DNA after electrophoresis or enzyme digestion was performed with E.

Gene modules were transformed into E. Further transformation of other basic genetic module s into a constructed E. Recombinant E. TABLE 1 List of recombinant strains, the plasmids contained in the strains, and the cascade biotransformation catalyzed by the strains. Cascade Strain [a] Recombinant plasmids [b] in the strain Reactions E. A representative example of an enzyme catalytic cascade is the conversion of substituted styrene to chiral substituted S -phenylethanol amine and S -phenylglycine FIG.

Previously, we engineered E. Module 2 effects the terminal oxidation of S -phenylethane diol to S -mandelic acid by alcohol dehydrogenase and aldehyde dehydrogenase FIG. PCT Application No. The recombinant E. General Procedure 2: Growing of E. The cell pellets were resuspended in an appropriate buffer to the desired density as resting cells for biotransformation.

The mixture was shaken at r. At 12 h, additional glucose 0. To determine the e. The reaction mixture was shaken at r. At 20 h, additional glucose 0. Briefly, Module 3 is a cascade transformation, which includes oxidation of terminal alcohol to aldehyde and reductive amination of aldehyde to amine. As AlkJ catalyzed the highly regioselective oxidation of S -phenylethane diol to S -mandelaldehyde in Module 2, it is also used as the first enzyme in Module 3. To increase the yield of amine and utilize the easily available ammonia as amine donor, we employed L-alanine dehydrogenase AlaDH from Bacillus subtilis to regenerate L-alanine from pyruvate using ammonia.

The ligation product was transformed heat shock into E. Similarly, Module 3 was also sub-cloned to other three vectors by the following procedures. When OD reached 0. This result showed that the constructed recombinant strain is a powerful catalyst for the cascade biotransformation of S -phenylethane diol to S -phenylethanol amine. Briefly, Module 4 requires a cascade transformation of S -mandelic acid to S -phenylglycine via oxidation and reductive amination FIG.

Two different enzymes were known to oxidize S -mandelic acid to phenylglyoxylic acid: S -mandelate dehydrogenase MDH in the mandelic acid degradation pathway of Pseudomonas putida ATCC , and hydroxymandelate oxidase HMO in the vancomycin biosynthesis pathway of Streptomyces coelicolor A3 2. Both enzymes were successfully cloned and overexpressed in E. Clearly, HMO showed higher activity and fully converted 50 mM substrates in 24 h. Thus, HMO was chosen for the Module 4.

The second reaction in Module 4 is enantioselective amination of phenylglyoxylic acid to L-phenylglycine. The E. As shown in FIG. Obviously, the transamination is a reversible reaction and difficult to complete in this reaction. The glutamate dehydrogenase GluDH from E. The corresponding E. With that, Module 4 containing four enzymes was constructed FIG.

Cascade transformation was optimized to convert 45 mM S -mandelic acid to This result showed that the constructed recombinant strain is a powerful catalyst for the cascade biotransformation of S -mandelic acid to S -phenylglycine. To achieve formal asymmetric aminohydroxylation of styrene to chiral S -phenylethanol amine FIG. Four E. Next, 0. The recombinant cells were spread on LB agar plates with two appropriate antibiotics. The twelve combinatorial transformations gave twelve E. Since the reaction is complex, the cascade reaction was first optimized by applying different amount of glucose and ammonia.

Biotransformation of 50 mM styrene was performed with resting cells of E. The twelve recombinant E. A 2 mL n-hexadecane containing styrene 50 mM was added to the reaction system to form a second phase. Using the optimal condition, all the twelve E. This result demonstrated the feasibility of the cascade biotransformation of alkenes styrene to chiral amino alcohols S -phenylethanol amine. The current system can be further improved with optimization of reaction conditions or using more efficient enzymes. The best E. A 2 mL n-hexadecane containing styrene 60 mM was added to the reaction system to form a second phase.

Additional 0. It is worth noting that unreacted substrates, intermediates, and by-products were kept in low amounts 5 mM. More importantly, R -phenylethanol amine phenylglycinol was not observed, indicating the high stereo-selectivity of the cascade biotransformation. The result demonstrated the potential of the cascade biotransformation for further scaling up and optimization. A 2 mL n-hexadecane containing substituted styrene 20 mM was added to the reaction system to form a second phase. The enantiomeric excess e.

As shown in Table 2, all the eleven substituted S -phenylethanol amines were produced in good to excellent e. TABLE 2 Regio- and enantioselective one-pot conversion of substituted styrenes 1a-k to substituted S -phenylethanol amines 6a-k with E. The following four E. These four strains served as parental strains for further integration with Module 4. The Journal of Organic Chemistry , 84 3 , Zirong Zhang, David B. Journal of the American Chemical Society , 1 , The Journal of Organic Chemistry , 83 24 , Mahesh D.

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361L Chiral Resolution of Phenylsuccinic Acid (#6) - updated thorough mixing and washing

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US20080314835A1 - Chiral separating agents with active support - Google Patents

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