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Tytuł:
Enancjoselektywna enzymatyczna desymetryzacja katalizowana oksydoreduktazami. Reakcje utleniania. Część 1
Enantioselective enzymatic desymmetrization catalyzed by oxidoreductases. Oxidation reactions. Part 1
Autorzy:
Karczmarska-Wódzka, A.
Kołodziejska, R.
Tafelska-Kaczmarek, A.
Studzińska, R.
Wróblewski, M.
Augustyńska, B.
Powiązania:
https://bibliotekanauki.pl/articles/172799.pdf
Data publikacji:
2015
Wydawca:
Polskie Towarzystwo Chemiczne
Tematy:
dehydrogenaza
monooksygenaza
reakcja utleniania
dehydrogenase
monooxygenase
oxidation reaction
Opis:
The main advantage of biotransformation involving enzymes, compared to chemical processes, is a highly selective formation of products with precise configuration. Herein we describe enzymes participating in the oxidation processes, especially dehydrogenases and monooxygenases. Dehydrogenases are not only able to catalyze the enantioselective reduction of prochiral ketones, but they can also desymmetrize meso and prochiral diols through the enantioselective oxidation. As a result of this processes, optically active hydroxyketones, hydroxycarboxylic acids, and their derivatives are obtained. Cytochrome P450 monooxygenases (CYPs) constitute a family of heme-containing enzymes which exhibits a variety of catalytic activities. They catalyze different reactions, such as hydroxylation, epoxidation, oxidative deamination, or N- and (S)-oxidation. In the oxidation reaction with monooxygenases, the whole cells are commonly used as catalysts. The use of monooxygenases in the oxidation reaction of prochiral alkanes provides the optically active alcohols. It is very significant that these transformations are still difficult to carry out by chemical methods. Baeyer-Villiger monooxygenases (BVMO EC 1.14.13.X) effectively catalyze the nucleophilic and electrophilic oxidation reactions of various functional groups. BVMO are highly regio- and stereoselective enzymes, and their catalytic potential is used in the synthesis of optically pure lactones and esters. Keywords:
Źródło:
Wiadomości Chemiczne; 2015, 69, 1-2; 35-51
0043-5104
2300-0295
Pojawia się w:
Wiadomości Chemiczne
Dostawca treści:
Biblioteka Nauki
Artykuł
Tytuł:
Enancjoselektywna enzymatyczna desymetryzacja katalizowana oksydoreduktazami. Reakcje utleniania. Część 2
Enantioselective enzymatic desymmetrization catalyzed by oxidoreductases. Oxidation reactions. Part 2
Autorzy:
Karczmarska-Wódzka, A.
Kołodziejska, R.
Tafelska-Kaczmarek, A.
Studzińska, R.
Wróblewski, M.
Augustyńska, B.
Powiązania:
https://bibliotekanauki.pl/articles/172457.pdf
Data publikacji:
2015
Wydawca:
Polskie Towarzystwo Chemiczne
Tematy:
dioksygenaza
oksydaza
peroksydaza
reakcja utleniania
dioxygenase
oxidase
peroxidase
oxidation reaction
Opis:
In continuation of our work, we herein describe next enzyme classes applied for oxidation reaction. Dioxygenases, oxidases, and peroxidases are successfully used in the synthesis of desymmetrization products with high yields and enantiomeric excesses. Aromatic dioxygenases, such as toluene dioxygenase (TDO), naphthalene dioxygenase (NDO), and biphenyl dioxygenase (BPDO) found in the prokaryotic microorganisms are enzymes belonging to the dioxygenase class and are the most commonly used in organic synthesis. The α-oxidation of various fatty acids in the presence of an α-oxidase from germinating peas is one of the few examples of oxidases application in asymmetric organic synthesis. The intermediary α-hydroxyperoxyacids can undergo two competing reactions: decarboxylation of the corresponding aldehydes or reduction to the (R)-2-hydroxy acids. In order to eliminate the competitive decarboxylation reaction tin(II) chloride is used as an in situ reducing agent. Peroxidases are the redox enzymes found in various sources such as animals, plants, and microorganisms. Due to the fact that, in contrast to monooxygenases, no additional cofactors are required, peroxidases are highly attractive for the preparative biotransformation. Oxidation reactions catalyzed by (halo)peroxydases are also often used in organic synthesis. N-Oxidation of amines, for instance, leads to the formation of the corresponding aliphatic N-oxides, aromatic nitro-, or nitrosocompounds. From a preparative synthesis standpoint, however, sulfoxidation of thioether is important since it was proven to proceed in a highly stereo- and enantioselective manner. Furthermore, depending on the source of haloperoxidase, chiral sulfoxides of opposite configurations can be obtained.
Źródło:
Wiadomości Chemiczne; 2015, 69, 1-2; 53-64
0043-5104
2300-0295
Pojawia się w:
Wiadomości Chemiczne
Dostawca treści:
Biblioteka Nauki
Artykuł
    Wyświetlanie 1-2 z 2

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