Mirror-image packing in enantiomer discrimination molecular basis for the enantioselectivity of B.cepacia lipase toward 2-methyl-3-phenyl-1-propanol.

@article{Mezzetti2005MirrorimagePI,
  title={Mirror-image packing in enantiomer discrimination molecular basis for the enantioselectivity of B.cepacia lipase toward 2-methyl-3-phenyl-1-propanol.},
  author={Alessandra Mezzetti and Joseph D. Schrag and Chan Seong Cheong and Romas J. Kazlauskas},
  journal={Chemistry \& biology},
  year={2005},
  volume={12 4},
  pages={
          427-37
        }
}
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59 Citations
Background Citations
3
Methods Citations
2

59 Citations

Molecular Basis of Chiral Acid Recognition by Candida rugosa Lipase: X‐Ray Structure of Transition State Analog and Modeling of the Hydrolysis of Methyl 2‐Methoxy‐2‐phenylacetate
TLDR
The X-ray crystal structure of a transition-state analog covalently linked to CRL was determined to understand how Candida rugosa lipase (CRL) distinguishes between enantiomers of chiral acids, and phosphonate (RC,RPSP)-3, which, upon reaction with CRL, mimics the transition state for hydrolysis of (S)-1-methyl ester, the fast-reacting enantiomer.
Molecular Basis for the Enantio- and Diastereoselectivity of Burkholderia cepacia Lipase toward γ-Butyrolactone Primary Alcohols
Burkholderia cepacia lipase (BCL) shows high enantioselectivity toward chiral primary alco- hols, but this enantioselectivity is often unpredicta- ble, especially for substrates that contain an…
Mirror‐Image Packing Provides a Molecular Basis for the Nanomolar Equipotency of Enantiomers of an Experimental Herbicide
TLDR
A series of crystallographic studies of complexes between an enzyme and a potent experimental herbicide whose chiral center forms an essential part of the inhibitor pharmacophore determine that both enantiomers make equivalent pseudosymmetric interactions in the active site, thus mimicking an achiral reaction intermediate.
Enantioselective Anion Recognition by Chiral Halogen-Bonding [2]Rotaxanes.
TLDR
This work combined the stringent linear geometric interaction constraints of halogen bonding (XB), the noncovalent interaction between an electrophilic halogen atom and a Lewis base, with highly preorganized and conformationally restricted chiral cavities of [2]rotaxanes to achieve enantioselective anion recognition.
Insight of Pseudomonas cepacia lipase enantioselectivity towards chiral 1-phenyl ethanol and its derivates
A systematic research of PCL (Pseudomonas cepacia lipase) catalyzed kinetic resolution of 1-phenyl ethanol and its derivatives have been done. PCL shows a high activity toward 1-phenyl ethanol and…
Prediction of enantioselectivity of lipase catalyzed kinetic resolution using umbrella sampling.
Through the looking glass: Chiral recognition of substrates and products at the active sites of racemases and epimerases.
TLDR
Recognition that mirror-image packing is the common binding mode for enantiomeric or epimeric substrates of these enzymes should inform modelling/docking studies and protein engineering.
Computational Study of the Lipase‐Mediated Desymmetrisation of 2‐Substituted‐Propane‐1,3‐Diamines
TLDR
Analysis of the MDS trajectories revealed that the homologation of 2‐aryl substituents by means of a methylene group lowers enantioselectivity by alleviating the conformational tension of the slow‐reacting orientations due to unfavourable intramolecular contacts between the ortho carbons of the aryl group and the nucleophilic nitrogen.
Molecular Basis for the Stereoselective Ammoniolysis of N‐Alkyl Aziridine‐2‐Carboxylates Catalyzed by Candida antarctica Lipase B
TLDR
Success in rationalizing the enantioselectivity supports the notion that an umbrella‐like‐inversion orientation can contribute to enantiOSElectivity in lipases.
The active site of an enzyme can host both enantiomers of a racemic ligand simultaneously.
TLDR
While the question of singleenantiomer drugs has been settled for the end of the drugdiscovery process, racemic mixtures are still preferentially used in primary screens, mainly because of by the considerable efforts necessary to produce enantiomerically pure drugs.
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TLDR
This work used a combination of molecular modeling of lipase-transition state analogue complexes and kinetic measurements to identify the molecular basis of the enantioselectivity of PCL toward two primary alcohols: 2-methyl-3-phenyl-1-propanol, 1, and 2-phenoxy- 1-pro panol, 2.
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TLDR
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TLDR
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Remarkable remote chiral recognition in a reaction mediated by a catalytic antibody.
TLDR
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