Enantioselective Hydrolysis of Bromo- and Methoxy-Substituted 1-Phenylethanol Acetates Using Carrot and Celeriac Enzymatic Systems

2007 ◽  
Vol 62 (5-6) ◽  
pp. 397-402 ◽  
Author(s):  
Wanda K. Mączka ◽  
Agnieszka Mironowicz
Keyword(s):  
Aromatic Ring ◽  
Opposite Effect ◽  
Bromine Atom ◽  
Apium Graveolens ◽  
Enantioselective Hydrolysis ◽  
Daucus Carota L ◽  
Oxidation Of Alcohols ◽  
Enzymatic Systems ◽  
Hydrolysis Of ◽  
Substituted 1

Enantioselective hydrolysis of bromo- and methoxy-substituted 1-phenylethanol acetates was conducted using comminuted carrot (Daucus carota L.) and celeriac (Apium graveolens L. var. rapaceum) roots. Hydrolysis of the acetates led to alcohols, preferentially to R-(+)- enantiomers. Efficiencies of both reactions - hydrolysis of the acetates with an electrondonating methoxy group and oxidation of the resulting alcohols - increased in the following order: ortho < meta < para. The presence of an electron-withdrawing bromine atom in the aromatic ring had the opposite effect. Oxidation of alcohols with both types of substituents in the aromatic ring showed that location of a substituent had stronger impact on the oxidation rate than its electronic properties.

Biotransformation of Isoprenoids and Shikimic Acid Derivatives by a Vegetable Enzymatic System

2004 ◽  
Vol 59 (3-4) ◽  
pp. 201-204 ◽  
Author(s):  
Wanda Krystyna Mączka ◽  
Agnieszka Mironowicz
Keyword(s):  
Daucus Carota ◽  
Shikimic Acid ◽  
Methyl Esters ◽  
Reversible Reaction ◽  
Apium Graveolens ◽  
Enzymatic System ◽  
Aromatic Acids ◽  
Daucus Carota L ◽  
Enzymatic Systems ◽  
Armoracia Lapathifolia

In biotransformations carried out under similar conditions enzymatic systems from carrot (Daucus carota L.), celeriac (Apium graveolens L. var. rapaceum) and horse-radish (Armoracia lapathifolia Gilib.) hydrolyzed the ester bonds of acetates of phenols or alicyclic alcohols. Nevertheless, methyl esters of aromatic acids did not undergo hydrolysis. Alcohols were oxidized to ketones in a reversible reaction.

ChemInform Abstract: Lipase-Catalyzed Enantioselective Hydrolysis of Bicyclo[3.2.0]heptanol Esters in Supercritical Carbon Dioxide.

ChemInform ◽  
2010 ◽  
Vol 28 (34) ◽  
pp. no-no
Author(s):  
O. PARVE ◽  
I. VALLIKIVI ◽  
L. LAHE ◽  
A. METSALA ◽  
UE. LILLE ◽  
...  
Keyword(s):  
Carbon Dioxide ◽  
Supercritical Carbon Dioxide ◽  
Enantioselective Hydrolysis ◽  
Hydrolysis Of ◽  
Supercritical Carbon

ChemInform Abstract: Perfect Enantioselective Hydrolysis of Amino Acid Esters by Modified . alpha.-Chymotrypsin.

ChemInform ◽  
2010 ◽  
Vol 26 (21) ◽  
pp. no-no
Author(s):  
R. UEOKA ◽  
J. OKAI ◽  
K. SHIMADA ◽  
D. SEGAWA ◽  
T. NAKATA ◽  
...  
Keyword(s):  
Amino Acid ◽  
Enantioselective Hydrolysis ◽  
Amino Acid Esters ◽  
Hydrolysis Of ◽  
Acid Esters

scholarly journals Plant-Mediated Biotransformations of S(+)- and R(–)-Carvones

2018 ◽  
Vol 8 (12) ◽  
pp. 2605 ◽  
Author(s):  
Wanda Mączka ◽  
Daria Sołtysik ◽  
Katarzyna Wińska ◽  
Małgorzata Grabarczyk ◽  
Antoni Szumny
Keyword(s):  
Solanum Tuberosum L ◽  
Apium Graveolens ◽  
Petroselinum Crispum ◽  
Enzymatic System ◽  
Enantiomerically Pure ◽  
Daucus Carota L ◽  
Pyrus Communis L ◽  
Substrate Conversion ◽  
Diastereomeric Excess ◽  
Reduction Of Ketones

The enzymatic system of vegetables is well known as an efficient biocatalyst in the stereoselective reduction of ketones. Therefore, we decided to use the comminuted material of several plants including five vegetables (Apium graveolens L., Beta vulgaris L., Daucus carota L., Petroselinum crispum L., and Solanum tuberosum L.) and three fruits (Malus pumila L. “Golden” and “Kortland” as well as Pyrus communis L. “Konferencja”) to obtain enantiomerically pure carveol, which is commercially unavailable. Unexpectedly, all of the used biocatalysts not only reduced the carbonyl group of (4R)-(–)-carvone and (4S)-(+)-carvone, but also reduced the double bond in the cyclohexene ring. The results revealed that (4R)-(–)-carvone was transformed into (1R, 4R)- and (1S, 4R)-dihydrocarvones, and (1R,2R,4R)-dihydrocarveol. Although the enzymatic system of the potato transformed the substrate almost completely, the %de was not the highest. Potato yielded 92%; however, when carrot was used as the biocatalyst, it was possible to obtain 17% of (1R, 4R)-(+)-dihydrocarvone with 100% diastereomeric excess. In turn, the (4S)-(+)-carvone was transformed, using the biocatalysts, into (1R, 4S)- and (1S, 4S)-dihydrocarvones and dihydrocarveols. Complete substrate conversion was observed in biotransformation when potato was used. In the experiments using apple, (1R, 4S)-dihydrocarvone with 100% diastereomeric excess was obtained. Using NMR spectroscopy, we confirmed both diastereoisomers of 4(R)-1,2-dihydrocarveols, which were unseparated in the GC condition. Finally, we proved the high usefulness of vegetables for the biotransformation of both enantiomers of carvone as well as dihydrocarvone.

Selectivity-enhancement in enantioselective hydrolysis of sec-alkyl sulfates by an alkylsulfatase from Rhodococcus ruber DSM 44541

2002 ◽  
Vol 13 (13) ◽  
pp. 1443-1447 ◽  
Author(s):  
Mateja Pogorevc ◽  
Ulrike T. Strauss ◽  
Thomas Riermeier ◽  
Kurt Faber
Keyword(s):  
Enantioselective Hydrolysis ◽  
Rhodococcus Ruber ◽  
Alkyl Sulfates ◽  
Hydrolysis Of
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