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Literature summary for 2.6.1.18 extracted from

  • Buss, O.; Voss, M.; Delavault, A.; Gorenflo, P.; Syldatk, C.; Bornscheuer, U.; Rudat, J.
    beta-Phenylalanine ester synthesis from stable beta-keto ester substrate using engineered omega-transaminases (2018), Molecules, 23, 1211 .
    View publication on PubMedView publication on EuropePMC
Search for more literature for 2.6.1.18

Application

Application Comment Organism
synthesis a prominent example for beta-amino acids in pharmaceuticals is beta-phenylalanine, present in the natural substance paclitaxel (Taxol), which is a prominent anti-cancer agent. Method development for production of chiral beta-phenylalanine ethyl ester, which can be chemically or enzymatically hydrolyzed to (R)- or (S)-phenylalanine. Asymmetric synthesis of the beta-phenylalanine ethyl ester an upscaling, overview uncultured bacterium

Cloned(Commentary)

Cloned (Comment) Organism
recombinant expression of His-tagged enzyme in Escherichia coli strain BL21(DE3) uncultured bacterium

Protein Variants

Protein Variants Comment Organism
additional information development of beta-phenylalanine ester synthesis method from stable beta-keto ester substrate using engineered omega-transaminase. The omega-transaminase mutants 3FCR_4M and ATA117 11Rd show great potential for further engineering experiments aiming at the synthesis of chiral (S)- and (R)-phenylalanine esters. This alternative approach results in the conversion of 32% and 13% for the (S)- and (R)-enantiomer, respectively. Furthermore, the (S)-phenylalanine ethyl ester is isolated by performing a semi-preparative synthesis uncultured bacterium

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
L-alanine + 3-oxopropanoate uncultured bacterium
-
 pyruvate + beta-alanine
-
 r

Organism

Organism UniProt Comment Textmining
uncultured bacterium
-
 omega-transaminase library screening
-

Purification (Commentary)

Purification (Comment) Organism
recombinant His-tagged enzyme from Escherichia coli strain BL21(DE3) by nickel affinity chromatography uncultured bacterium

Reaction

Reaction Comment Organism Reaction ID
L-alanine + 3-oxopropanoate = pyruvate + beta-alanine the reaction mechanism of transaminase-catalyzed reactions consists of two half-reactions and is described as a ping-pong-bi-bi mechanism uncultured bacterium
a

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
(S)-1-phenylethylamine + 3-oxopropanoate
-
 uncultured bacterium acetophenone + beta-alanine
-
 r
ethyl benzoylacetate + o-xylylenediamine
-
 uncultured bacterium beta-phenylalanine ethyl ester + ?
-
 ?
isopropylamine + 3-oxopropanoate
-
 uncultured bacterium acetone + beta-alanine
-
 r
L-alanine + 3-oxopropanoate
-
 uncultured bacterium pyruvate + beta-alanine
-
 r
additional information development of beta-phenylalanine ester synthesis method from stable beta-keto ester substrate using engineered omega-transaminase. The omega-transaminase mutants 3FCR_4M and ATA117 11Rd show great potential for further engineering experiments aiming at the synthesis of chiral (S)- and (R)-phenylalanine esters. This alternative approach results in the conversion of 32% and 13% for the (S)- and (R)-enantiomer, respectively. Furthermore, the (S)-phenylalanine ethyl ester is isolated by performing a semi-preparative synthesis uncultured bacterium ?
-
-

Synonyms

Synonyms Comment Organism
3FCR_4M mutant
-
 uncultured bacterium
ATA117 11Rd mutant
-
 uncultured bacterium
omega-transaminase
-
 uncultured bacterium

Temperature Optimum [°C]

Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
30
-
 assay at uncultured bacterium

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
7.5
-
 assay at uncultured bacterium

Cofactor

Cofactor Comment Organism Structure
pyridoxal 5'-phosphate PLP uncultured bacterium

General Information

General Information Comment Organism
evolution fold type I and IV of PLP-dependent omega-transaminases (omega-TAs) show (R)- and (S)-selectivity, respectively uncultured bacterium
additional information the reaction mechanism of transaminase-catalyzed reactions consists of two half-reactions and is described as a ping-pong-bi-bi mechanism. The widespread alpha-TAs are limited to alpha-amino acids, containing the amino or keto group in the alpha position to a carboxylic function. In contrast, omega-TAs are able to transfer amino groups in different positions to the carboxylic moiety or even in the absence of carboxylic functions uncultured bacterium