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
        }
}
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
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.
...
...

References

SHOWING 1-10 OF 42 REFERENCES
Molecular Basis for Enantioselectivity of Lipase from Pseudomonas cepacia toward Primary Alcohols. Modeling, Kinetics, and Chemical Modification of Tyr29 to Increase or Decrease Enantioselectivity.
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.
Enantioselectivity of the Pseudomonas cepacia lipase towards 2-methyl-3-(or 4)-arylalkanols: an approach based on stereoelectronic theory and the molecular modeling
For a better understanding of the previously reported enantiose-lectivity of Pseudomonas cepacia lipase (PCL) in acylation of racemic primary alcohols, 2-methyl-3(or 4)-arylalkanols, molecular
Differences in binding modes of enantiomers of 1-acetamido boronic acid based protease inhibitors: crystal structures of gamma-chymotrypsin and subtilisin Carlsberg complexes.
TLDR
The structural factors responsible for the differences in stereoselectivity between the two enzymes have been explored by X-ray crystallographic examination of subtilisin Carlsberg and gamma-chymotrypsin complexes of the L- and D-enantiomers of p-chlorophenyl and 1-naphthyl boronic acid derivatives.
Stereoselectivity of Pseudomonas cepacia lipase toward secondary alcohols: A quantitative model
TLDR
A simple model can be applied to predict enantioselectivity of P. cepacia lipase toward a broad range of secondary alcohols.
STUDIES ON HYDROLYSIS OF CHIRAL, ACHIRAL AND RACEMIC ALCOHOL ESTERS WITH PSEUDOMONAS CEPACIA LIPASE : MECHANISM OF STEREOSPECIFICITY OF THE ENZYME
TLDR
Results were interpreted to indicate that LM of the slow-reacting enantiomer is positioned close to the imidazole ring of the catalytic His and hinders NIµ2 of the residue from forming a weak interaction with O1 of the leaving alcohol and that the breakdown of the tetrahedral intermediate is thus inhibited.
Enzymatic resolution of 2-phenoxy-1-propanols through the enantioselective acylation mediated by Achromobacter sp. lipase
TLDR
2-(Substituted phenoxy)-1-propanols, belonging to primary alcohols with an oxygen atom at the stereocenter, were resolved with moderate to good enantioselectivity through the enantiOSElective acylation with vinyl butanoate mediated by the little-known lipase from Achromobacter sp.
Remarkable remote chiral recognition in a reaction mediated by a catalytic antibody.
TLDR
Surprisingly, the electron densities of the liganded phosphonates, 7D and 7L, within the D2.3 binding/reaction site were essentially identical, highlighting the subtle influences of protein interactions on chemical behavior.
...
...