- But-2-ene-1,4-diamine and But-2-ene-1,4-diol as Donors for Thermodynamically Favored Transaminase- and Alcohol Dehydrogenase-Catalyzed Processes
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Both cis- and trans-but-2-ene-1,4-diamines have been prepared and efficiently applied as sacrificial cosubstrates in enzymatic transamination reactions. The best results were obtained with the cis-diamine. The thermodynamic equilibrium of the stereoselective transamination process is shifted to the amine formation due to tautomerization of 5H-pyrrole into 1H-pyrrole, achieving high conversions (78–99%) and enantiomeric excess (up to >99%) by using a small excess of the amine donor. Furthermore, when the reaction proceeded, a strong coloration was observed due to polymerization of 1H-pyrrole. A structurally related compound, cis-but-2-ene-1,4-diol, has been utilized as cosubstrate in different alcohol dehydrogenase (ADH)-mediated bioreductions. In this case, high conversions (91–99%) were observed due to a lactonization process. Both strategies are convenient from both synthetic and atom economy points of view in the production of valuable optically active products. (Figure presented.).
- Martínez-Montero, Lía,Gotor, Vicente,Gotor-Fernández, Vicente,Lavandera, Iván
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supporting information
p. 1618 - 1624
(2016/10/13)
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- Asymmetric Biocatalytic Amination of Ketones at the Expense of NH3 and Molecular Hydrogen
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A biocatalytic system is presented for the stereoselective amination of ketones at the expense of NH3 and molecular hydrogen. By using a NAD+-reducing hydrogenase, an alanine dehydrogenase, and a suitable ω-transaminase, the R- as well as the S-enantiomer of various amines could be prepared with up to >99% ee and 98% conversion. (Chemical Equation Presented).
- Holzer, Anja K.,Hiebler, Katharina,Mutti, Francesco G.,Simon, Robert C.,Lauterbach, Lars,Lenz, Oliver,Kroutil, Wolfgang
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supporting information
p. 2431 - 2433
(2015/06/02)
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- Transaminases applied to the synthesis of high added-value enantiopure amines
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Critical parameters affecting the stereoselective amination of (hetero)aromatic ketones using transaminases have been studied, such as temperature, pH, substrate concentration, cosolvent, and source and percentage of amino donor, to further optimize the production of enantiopure amines using both (S)- and (R)-selective biocatalysts from commercial suppliers. Interesting enantiopure amino building blocks have been obtained, overcoming some limitations of traditional chemical synthetic methods. Representative processes were scaled up, affording halogenated and heteroaromatic amines in enantiomerically pure form and good isolated yields.
- Paul, Caroline E.,Rodriguez-Mata, Maria,Busto, Eduardo,Lavandera, Ivan,Gotor-Fernandez, Vicente,Gotor, Vicente,Garcia-Cerrada, Susana,Mendiola, Javier,De Frutos, Oscar,Collado, Ivan
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supporting information
p. 788 - 792
(2014/07/08)
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- N-BIPHENYLMETHYLINDOLE MODULATORS OF PPARG
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The invention provides molecular entities that bind with high affinity to PPARG (PPAR3), inhibit kinase-mediated, e.g., cdk5-mediated, phosphorylation of PPARG, but do not exert an agonistic effect on PPARG. Compounds of the invention can be used for treatment of conditions in patients wherein PPARG plays a role, such as diabetes, insulin resistance, impaired glucose tolerance, pre-diabetes, hyperglycemia, hyperinsulinemia, obesity, or inflammation. In methods of treatment of these conditions using a compound of the invention, the compound can avoid producing side effects of significant weight gain, edema, impairment of bone growth or formation, or cardiac hypertrophy, or any combination thereof, in the patient receiving the compound. Methods of preparation of the compounds, bioassay methods for evaluating compounds of the invention as non-agonistic PPARG binding compounds, and pharmaceutical compositions are also provided.
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Page/Page column 189
(2012/12/14)
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- A fast and sensitive assay for measuring the activity and enantioselectivity of transaminases
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A fast and sensitive method for screening transaminase activity and enantioselectivity, using d- and l-amino acid oxidases, allows new amine substrates to be rapidly identified. The Royal Society of Chemistry 2011.
- Hopwood, Jennifer,Truppo, Matthew D.,Turner, Nicholas J.,Lloyd, Richard C.
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supporting information; experimental part
p. 773 - 775
(2011/04/15)
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- PYRIDAZINONE DERIVATIVES AND USE THEREOF AS P2X7 RECEPTOR INHIBITORS
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Novel pyridazinone compounds of formula (I), which inhibit the purinergic P2X7 receptor and are useful for prevention, therapy and improvement of inflammatory and immunological diseases.
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Page/Page column 138-140
(2009/06/27)
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- An easy route to optically active 1-substituted-1-pyridyl-methylamines by diastereoselective reduction of enantiopure N-tert-butanesulfinyl ketimines
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The reduction of enantiopure N-tert-butanesulfinyl ketimines derived from pyridyl ketones afforded the related N-tert-butanesulfinyl amines with high yields and diastereoselectivities.
- Chelucci, Giorgio,Baldino, Salvatore,Chessa, Simona,Pinna, Gerard A.,Soccolini, Franco
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p. 3163 - 3169
(2007/10/03)
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- CONDENSED HETEROCYCLIC COMPOUNDS AS CALCITONIN AGONISTS
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The present invention relates to novel fused heterocyclic ring system compounds and methods for their use in the treatment and prevention of diseases or conditions which are related to irregular calcification.
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Page/Page column 39
(2010/02/07)
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