Dioxygenase-catalyzed cis-dihydroxylation of pyridine-ring systems

2002 ◽  
Vol 80 (6) ◽  
pp. 589-600 ◽  
Author(s):  
Derek R Boyd ◽  
Narain D Sharma ◽  
Ludmila V Modyanova ◽  
Jonathan G Carroll ◽  
John F Malone ◽  
...  
Keyword(s):  
Pseudomonas Putida ◽  
Pyridine Ring ◽  
Enantiomeric Excess ◽  
Ring Systems ◽  
Toluene Dioxygenase ◽  
Whole Cells ◽  
The Absolute ◽  
Carbocyclic Rings

Toluene dioxygenase-catalyzed dihydroxylation, in the carbocyclic rings of quinoline, 2-chloroquinoline, 2-methoxyquinoline, and 3-bromoquinoline, was found to yield the corresponding enantiopure cis-5,6- and -7,8-dihy dro diol metabolites using whole cells of Pseudomonas putida UV4. cis-Dihydroxylation at the 3,4-bond of 2-chloroquino line, 2-methoxyquinoline, and 2-quinolone was also found to yield the heterocyclic cis-dihydrodiol metabolite, (+)-cis-(3S,4S)-3,4-dihydroxy-3,4-dihydro-2-quinolone. Heterocyclic cis-dihydrodiol metabolites, resulting from dihydroxylation at the 5,6- and 3,4-bonds of 1-methyl 2-pyridone, were isolated from bacteria containing toluene, naphthalene, and biphenyl dioxygenases. The enantiomeric excess (ee) values (>98%) and the absolute configurations of the carbocyclic cis-dihydrodiol metabolites of quinoline substrates (benzylic R) and of the heterocyclic cis-diols from quinoline, 2-quinolone, and 2-pyridone substrates (allylic S) were found to be in accord with earlier models for dioxygenase-catalyzed cis-dihydroxylation of carbocyclic arenes. Evidence favouring the dioxygenase-catalyzed cis-dihydroxylation of pyridine-ring systems is presented.Key words: dioxygenases; cis-dihydroxylation, pyridines, 2-pyridones, absolute configurations.

ChemInform Abstract: NEW ROUTES TO THE V-TRIAZOLO(1,5-A)PYRIDINE AND PYRAZOLO(1,5-A)PYRIDINE RING SYSTEMS

1975 ◽  
Vol 6 (41) ◽  
pp. no-no
Author(s):  
Y. TAMURA ◽  
J.-H. KIM ◽  
Y. MIKI ◽  
H. HAYASHI ◽  
M. IKEDA
Keyword(s):  
Pyridine Ring ◽  
Ring Systems

Enzymes in organic synthesis. 33. Stereoselective pig liver esterase-catalyzed hydrolyses of meso cyclopentyl-, tetrahydrofuranyl-, and tetrahydrothiophenyl-1,3-diesters

1985 ◽  
Vol 63 (2) ◽  
pp. 452-456 ◽  
Author(s):  
J. Bryan Jones ◽  
R. Scott Hinks ◽  
Philip G. Hultin
Keyword(s):  
Organic Synthesis ◽  
Absolute Configuration ◽  
Enantiomeric Excess ◽  
Membered Ring ◽  
Pig Liver ◽  
Pig Liver Esterase ◽  
Preparative Scale ◽  
Liver Esterase ◽  
The Absolute ◽  
Enzymes In Organic Synthesis

Preparative-scale pig liver esterase-catalyzed hydrolyses of five-membered ring meso-1,3-diesters are enantiotopically selective. While pro-S enantiotopic selectivity is exhibited in each case, the absolute configuration sense of the hydrolysis in the cyclopentyl series is opposite to that of both the tetrahydrofuranyl and tetrahydrothiophenyl diesters. The enantiomeric excess levels induced are in the 34–46% range.

scholarly journals Poly[[tetramethanolbis[4-oxo-3-(pyridin-4-yl)-1-(2,4,6-trichlorophenyl)-4,5-dihydro-1H-pyrazolo[3,4-d]pyrimidin-6-olato]disodium]–diethyl ether–methanol (1/1/2)]

IUCrData ◽  
2016 ◽  
Vol 1 (7) ◽  
Author(s):  
Bassam Abu Thaher ◽  
Dieter Schollmeyer ◽  
Stefan Laufer
Keyword(s):  
Diethyl Ether ◽  
Title Compound ◽  
Pyridine Ring ◽  
Heterocyclic Ring ◽  
Sodium Ion ◽  
Dihedral Angles ◽  
Ring Systems ◽  
Octahedral Environment

In the title compound, [Na2(C16H7Cl3N5O2)2(CH3OH)4]·C4H10O·2CH3OH, the central pyrazolo[3,4-d]pyrimidine system makes dihedral angles of 82.98 (7)° with the trichlorophenyl ring and 13.11 (15)° with the pyridine ring. The sodium ion has an octahedral environment, being coordinated by four methanol molecules and one O and one N atom of two different heterocyclic ring systems.

scholarly journals Stereoselective Esterase from Pseudomonas putida IFO12996 Reveals α/β Hydrolase Folds for d-β-Acetylthioisobutyric Acid Synthesis

2005 ◽  
Vol 187 (24) ◽  
pp. 8470-8476 ◽  
Author(s):  
Fatemeh Elmi ◽  
Hsin-Tai Lee ◽  
Jen-Yeng Huang ◽  
Yin-Cheng Hsieh ◽  
Yu-Ling Wang ◽  
...  
Keyword(s):  
Pseudomonas Putida ◽  
Enzyme Inhibitors ◽  
Specific Activity ◽  
Methyl Esters ◽  
Enantiomeric Excess ◽  
Angiotensin Converting Enzyme Inhibitors ◽  
Acid Synthesis ◽  
Ester Group ◽  
Catalytic Triad ◽  
Converting Enzyme Inhibitors

ABSTRACT Esterase (EST) from Pseudomonas putida IFO12996 catalyzes the stereoselective hydrolysis of methyl dl-β-acetylthioisobutyrate (dl-MATI) to produce d-β-acetylthioisobutyric acid (DAT), serving as a key intermediate for the synthesis of angiotensin-converting enzyme inhibitors. The EST gene was cloned and expressed in Escherichia coli; the recombinant protein is a non-disulfide-linked homotrimer with a monomer molecular weight of 33,000 in both solution and crystalline states, indicating that these ESTs function as trimers. EST hydrolyzed dl-MATI to produce DAT with a degree of conversion of 49.5% and an enantiomeric excess value of 97.2% at an optimum pH of about 8 to 10 and an optimum temperature of about 57 to 67°C. The crystal structure of EST has been determined by X-ray diffraction to a resolution of 1.6 Å, confirming that EST is a member of the α/β hydrolase fold superfamily of enzymes and includes a catalytic triad of Ser97, Asp227, and His256. The active site is located approximately in the middle of the molecule at the end of a pocket ∼12 Å deep. EST can hydrolyze the methyl ester group without affecting the acetylthiol ester moiety in dl-MATI. The examination of substrate specificity of EST toward other linear esters revealed that the enzyme showed specific activity toward methyl esters and that it recognized the configuration at C-2.

Benzylic monooxygenation catalyzed by toluene dioxygenase from Pseudomonas putida

Biochemistry ◽  
1988 ◽  
Vol 27 (4) ◽  
pp. 1360-1367 ◽  
Author(s):  
Lawrence P. Wackett ◽  
Lawrence D. Kwart ◽  
David T. Gibson
Keyword(s):  
Pseudomonas Putida ◽  
Toluene Dioxygenase
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