Preparation of enantiomerically pure N-heterocyclic amino alcohols by enzymatic kinetic resolution

@article{Tofani2015PreparationOE,
  title={Preparation of enantiomerically pure N-heterocyclic amino alcohols by enzymatic kinetic resolution},
  author={Giorgio Tofani and Antonella Petri and Oreste Piccolo},
  journal={Tetrahedron-asymmetry},
  year={2015},
  volume={26},
  pages={638-643}
}
View via Publisher
hdl.handle.net
8 Citations
Background Citations
1

8 Citations

One Pot Asymmetric Synthesis of (R)‐Phenylglycinol from Racemic Styrene Oxide via Cascade Biocatalysis
TLDR
A new three‐step one‐pot cascade system employing epoxide hydrolase, glycerol dehydrogenase, and ω‐transaminase was designed for the asymmetric synthesis of (R)‐phenylglycinol from racemic styrene oxide and optically pure (R).
Biosynthesis of chiral cyclic and heterocyclic alcohols via CO/C–H/C–O asymmetric reactions
Chiral cyclic and heterocyclic alcohols are important structural units for fine chemicals, agrochemicals, and chiral pharmaceuticals such as ladostigil, imbruvica, and sulopenem. Natural enzymes show…
Functional Characterization of a Marine Bacillus Esterase and its Utilization in the Stereo-Selective Production of D-Methyl Lactate
TLDR
BSE01701 was a very promising marine microbial esterase in the generation of chiral chemicals in industry and the addition of 60 % (v/v) organic co-solvent heptane could greatly improve both the enantiomeric excess of D-methyl lactate and the conversion.
Stereo-complementary bioreduction of saturated N-heterocyclic ketones
Enzymatic Enantioselective Hydrolysis of 2-(3-Chlorophenyl) Propionic Acid Ester Enhanced by PEG: Experiment and Optimization
Chiral resolution of 2-(3-chlorophenyl) propionic acid (CPA) via the hydrolysis of CPA ester catalyzed by lipase PS from Pseudomonas cepacia is reported. With polyethylene glycol (PEG 400) as a cos...
The role of Pseudomonas cepacia lipase in the asymmetric synthesis of heterocyclic based compounds
Use of Alcalase in the production of bioactive peptides: A review.
Lipases in asymmetric transformations: Recent advances in classical kinetic resolution and lipase–metal combinations for dynamic processes

References

SHOWING 1-10 OF 24 REFERENCES
Lipase-Catalyzed Practical Synthesis of (R)-1-Benzyl-3-hydroxy-2,5-pyrrolidinedione and Its Related Compounds
TLDR
Among several hydrolases examined here, lipase PS from Pseudomonas cepaciagave the best result in hydrolysis of (R)-1-benzyl-3-hydroxy-2,5-pyrrolidinedione, with a high enantioselectivity.
Enantioselective Catalysis, XIII. Preparative and Structural Chemistry of Chiral 3‐(Diphenylphosphanyl)‐pyrrolidiens and Their Palladium(II) Complexes
The preparation of both enantiomers of 3-diphenylphosphanylpyrrolidine (2) and several N-substituted derivatives together with two Pdn complexes of this ligand is reported. From L-malic acid and…
Practical synthetic process for enantiopure 1-benzyl-3-hydroxypyrrolidine
Enantioselective arylation of 2-methylacetoacetates catalyzed by CuI/trans-4-hydroxy-L-proline at low reaction temperatures.
TLDR
The combination of ligand, ortho substituent (participation of NHCOCF3), and solvent effects was shown to account for these unprecedentedly mild reaction conditions.
Hydrolases in Organic Synthesis: Regio- and Stereoselective Biotransformations
TLDR
Using Enantioselective Reactions to Design and Optimize Biocatalyst Performance and Survey of EnantiOSElective Protease-and Amidase-Catalyzed Reactions.
Purification and characterization of alcohol dehydrogenase reducing N-benzyl-3-pyrrolidinone from Geotrichum capitatum.
TLDR
This is the first report of (S)-N-benzyl-3-pyrrolidinol dehydrogenase activity in microorganisms and this enzyme will be very useful for the production of chiral compounds.
Characterization of novel alcohol dehydrogenase of Devosia riboflavina involved in stereoselective reduction of 3-pyrrolidinone derivatives
Synthesis of a variety of optically active hydroxylated heterocyclic compounds using epoxide hydrolase technology
Simple one-pot process for the bioresolution of tertiary amino ester protic ionic liquids using subtilisin
Evolving P450pyr hydroxylase for highly enantioselective hydroxylation at non-activated carbon atom.
Directed evolution of a monooxygenase to achieve very high enantioselectivity for hydroxylation at non-activated carbon atoms is demonstrated for the first time, where a triple mutant of P450pyr…
...
...