64869-63-2Relevant academic research and scientific papers
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)
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
Synthesis of Chiral Amines via a Bi-Enzymatic Cascade Using an Ene-Reductase and Amine Dehydrogenase
Jongkind, Ewald P. J.,Fossey-Jouenne, Aurélie,Mayol, Ombeline,Zaparucha, Anne,Vergne-Vaxelaire, Carine,Paul, Caroline E.
, (2021/12/23)
Access to chiral amines with more than one stereocentre remains challenging, although an increasing number of methods are emerging. Here we developed a proof-of-concept bi-enzymatic cascade, consisting of an ene reductase and amine dehydrogenase (AmDH), to afford chiral diastereomerically enriched amines in one pot. The asymmetric reduction of unsaturated ketones and aldehydes by ene reductases from the Old Yellow Enzyme family (OYE) was adapted to reaction conditions for the reductive amination by amine dehydrogenases. By studying the substrate profiles of both reported biocatalysts, thirteen unsaturated carbonyl substrates were assayed against the best duo OYE/AmDH. Low (5 %) to high (97 %) conversion rates were obtained with enantiomeric and diastereomeric excess of up to 99 %. We expect our established bi-enzymatic cascade to allow access to chiral amines with both high enantiomeric and diastereomeric excess from varying alkene substrates depending on the combination of enzymes.
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
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.
