64869-64-3Relevant academic research and scientific papers
Synthesis of (1R,3R)-1-amino-3-methylcyclohexane by an enzyme cascade reaction
Skalden, Lilly,Peters, Christin,Ratz, Lukas,Bornscheuer, Uwe T.
, p. 7207 - 7211 (2016/10/26)
Amine transaminases (ATAs) are powerful enzymes for the synthesis of chiral amines. Although the request for amines with more than one chiral center is increasing, their synthesis is still challenging. Here we show a casacde reaction combining an enoate r
Cascade Coupling of Ene-Reductases and ω-Transaminases for the Stereoselective Synthesis of Diastereomerically Enriched Amines
Monti, Daniela,Forchin, Maria Chiara,Crotti, Michele,Parmeggiani, Fabio,Gatti, Francesco G.,Brenna, Elisabetta,Riva, Sergio
, p. 3106 - 3109 (2015/10/19)
One-pot sequential and cascade processes performed by employing ene-reductases (ERs) together with ω-transaminases (ω-TAs) for the obtainment of diastereomerically enriched (R)- and (S)-amine derivatives containing an additional stereocenter were investigated. By using either α- or β-substituted unsaturated ketones as substrates and by coupling purified ERs belonging to the Old Yellow Enzyme (OYE) family with a panel of commercially available ω-TAs, the desired products were obtained in up to >99% conversion and >99%de. The sequential reactions were performed in a one-pot fashion with no need to adapt the reaction conditions to the reductive amination step or to purify the reaction intermediate. Moreover, high chemoselectivity of the tested ω-TAs for the saturated ketones was shown in the cascade reactions.
Two subtle amino acid changes in a transaminase substantially enhance or invert enantiopreference in cascade syntheses
Skalden, Lilly,Peters, Christin,Dickerhoff, Jonathan,Nobili, Alberto,Joosten, Henk-Jan,Weisz, Klaus,H?hne, Matthias,Bornscheuer, Uwe T.
, p. 1041 - 1045 (2015/05/05)
Amine transaminases (ATAs) are powerful enzymes for the stereospecific production of chiral amines. However, the synthesis of amines incorporating more than one stereocenter is still a challenge. We developed a cascade synthesis to access optically active
Biomimetic Polyene Cyclizations. Asymmetric Induction during the Acid-Catalyzed Cyclization of Chiral Imines
Demailly, Gilles,Solladie, Guy
, p. 3102 - 3108 (2007/10/02)
This paper reports the details of a basic study showing that an imino function is suitable to initiate acid-catalyzed cyclizations of polyenes, affording high yields of cyclized products.The additional advantage of such a function is to introduce very easily a chirality on the polyene skeleton by the way of a chiral group linked to nitrogen.The extent of asymmetric induction by a chiral phenethyl group on nitrogen is from 36percent to 65percent, according to the monocyclic or bicyclic nature of the substrate.
