enantis, s.r.o.
BRNO, CZECH REPUBLIC
Nadpis prezentace
practice 4:
BIOCATALYTIC PREPARATION OF PHARMACEUTICAL
PRECURSOR (S)-2-BROMOPENTANE
Veronika Štěpánková
Bi7430c MOLECULAR BIOTECHNOLOGY practice
enantis profile
 the first biotech spin-off of Masaryk University
 tight cooperation with the Loschmidt Laboratories
 consulting and development services in the field of enzyme
technologies and protein engineering
 own products based on dehalogenase enzymes
haloalkane dehalogenases
 cleavage of a carbon-halogen bond
 broad substrate specificity
 haloalkanes, haloalkenes, cyclohaloalkanes, haloalcohols, halohydrins,
haloethers, haloesters, haloamides and haloacetonitriles
 high enantioselectivity
 production of optically pure haloalkanes, alcohols,
halopolyols and polyols
 no cofactors
 chiral molecule
 has two enantiomeric forms
 does not have a plane of symmetry
 is not superposable with its mirror image
optical activity
 enantiomers
 may have substantially different biological effects!!!
optical activity
(S)-enantiomer
teratogenic
and carcinogen
(R)-enantiomer
sedative
or hypnotic
THALIDOMIDE
high optical purity (> 97 %) required in pharmaceutical
and agrochemical industry
synthesis of optically pure compounds
 chemical
synthesis of optically pure compounds
 chemical
 enzymatical
 enzymes are chiral biomolecules made from L-amino acids
 enzymes recognize chirality of substrate (kinetic resolution)
 enzymes are enantioselective
kinetic resolution
 theoretical maximum yield - 50%
 enantiomeric ratio (E ) - ratio of specificity constants
 E-value = 1 - enzyme is not stereoselective
 enantiomeric excess (e.e.) - enantiomeric purity
practice 4
 workflow
 preparation of reaction mixtures
 enantioselectivity measurement
 gas chromatography analysis
 calculation of enantiomeric excess and yield
 protocol
substrate
2-bromopentane
biocatalyst
haloalkane dehalogenase DbjA
contact
Veronika Štěpánková
Enantis, s.r.o.
INBIT Kamenice 34
625 00 Brno
+420-549 495 178
veronika@chemi.muni.cz