Synthesis of L-phenylalanine analogs byRhodotorula glutinis. Bioconversion of cinnamic acids derivatives

@article{Renard2005SynthesisOL,
  title={Synthesis of L-phenylalanine analogs byRhodotorula glutinis. Bioconversion of cinnamic acids derivatives},
  author={G. Renard and J. C. Guilleux and Clety Kwambai Bore and V. Malta-Valette and Dan A Lerner},
  journal={Biotechnology Letters},
  year={2005},
  volume={14},
  pages={673-678}
}
The synthesis of L-alpha aromatic amino acids by amination of forty-one derivatives of cinnamic acid and related compounds is tested with the yeastRhodotorula glutinis. 
View on Springer
22 Citations

22 Citations

Citation Type

Citation Type

Preparation of unnatural amino acids with ammonia-lyases and 2,3-aminomutases.
TLDR
This chapter discusses the biotransformations leading to various unnatural β-amino acids with phenylalanine 2,3-aminomutases using the same catalytic MIO prosthetic group.
Review: Biocatalytic transformations of ferulic acid: An abundant aromatic natural product
TLDR
In this review, the fascinating array of microbial and enzymatic transformations of ferulic acid is examined, including cinnamoyl side-chain cleavage; nonoxidative decarboxylation; mechanistic details of styrene formation; and reduction reactions.
A novel phenylalanine ammonia-lyase from Pseudozyma antarctica for stereoselective biotransformations of unnatural amino acids
Tailored Mutants of Phenylalanine Ammonia‐Lyase from Petroselinum crispum for the Synthesis of Bulky l‐ and d‐Arylalanines
TLDR
The synergistic multiple mutations resulted in substantial substrate scope extension of PcPAL and opened up new biocatalytic routes for the synthesis of both enantiomers of valuable phenylalanine analogues, such as (5‐phenylthiophene‐2‐yl)alanines.
Influence of Tyr78-loop on phenylalanine ammonia-lyase from Anabaena variabilis
TLDR
Catalytic activity of AvPAL could be improved by increasing the flexibility of Tyr78-loop through mutation on the Ser73 and Glu95 sites.
The interaction of heteroaryl-acrylates and alanines with phenylalanine ammonia-lyase from parsley.
TLDR
These results can be best explained by a Friedel-Crafts-type electrophilic attack at the aromatic part of the substrates as the initial step of the PAL reaction.
Expression and Properties of the Highly Alkalophilic Phenylalanine Ammonia-Lyase of Thermophilic Rubrobacter xylanophilus
TLDR
The extremely high pH optimum of RxPAL can be rationalized by a three-dimensional homology model indicating possible disulfide bridges, extensive salt-bridge formation and an excess of negative electrostatic potential on the surface.
Chemoenzymatic One-Pot Synthesis of Enantiopure L-Arylalanines from Arylaldehydes
Various enantiopure L-arylalanines can be prepared from the corresponding arylaldehydes in one-pot fashion by a combination of chemical and enzymatic reactions. The reagents used were…
Saturation Mutagenesis for Phenylalanine Ammonia Lyases of Enhanced Catalytic Properties
TLDR
Saturation mutagenesis at key residue I460 was performed in order to identify PcPAL variants of enhanced activity or to validate the superior catalytic properties of the rationally explored I460V P cPAL compared with the other possible mutant variants.
Fluorescent enzyme-coupled activity assay for phenylalanine ammonia-lyases
TLDR
The developed procedure provides a facile tool for the efficient activity screens of large mutant libraries of PALs in presence of non-natural substrates of interest, being essential for the substrate-specificity modifications/tailoring of PAL's through directed evolution-based protein engineering.
...
...

References

SHOWING 1-10 OF 14 REFERENCES
Inhibition of phenylalanine ammonia-lyase by cinnamic acid derivatives and related compounds
Biotransformation of trans-cinnamic acid to l-phenylalanine: Optimization of reaction conditions using whole yeast cells
Production of phenylalanine ammonia-lyase (PAL): isolation and evaluation of yeast strains suitable for commercial production of l-phenylalanine
TLDR
Results demonstrate the suitability and superiority of isolate SPA 10 for the commercial production of l-phenylalanine from trans-cinnamic acid.
Phosphinites of carbohydrates as chiral ligands for asymmetric synthesis catalyzed by complexes, I. Hydrogenation of aminoacid precursors by rhodium(I) chelates of methyl 4,6-O-benzylidente-2,3-bis-O-(diphenylphosphino)-α-D-glucopyranosides
A simple method for preparing carbohydrate-bis-phosphinites of methyl α-D-glucopyranosides of glucose and galactose protected by benzylidene groups in 4,6-position leads to chelating ligands which…
Parachlorophenylalanine produces dissociated effects on aggression “emotionality” and motor activity
"J."
however (for it was the literal soul of the life of the Redeemer, John xv. io), is the peculiar token of fellowship with the Redeemer. That love to God (what is meant here is not God’s love to men)…
Synthesis of Phenylalanine Analogs as Antimetabolites
Asymmetric alkylations of a phenylalanylglycinate equivalent. Novel route to dipeptides bearing .alpha.-alkyl-.alpha.-amino acid residues
Inhibition of Phenylalanine Ammonia-lyase by Flavonoids
Synthesis of pure p-chlorophenyl-L-alanine from L-phenylalanine.
...
...