- Enantioselective enzymatic acylation of 1-(3′-bromophenyl)ethylamine
-
An efficient biocatalytic process has been developed for the resolution of 1-(3′-bromophenyl)ethylamine (RS)-1 by way of enantioselective lipase-mediated (R)-selective acylation with ethyl 2-methoxyacetate to afford (S)-amine (S)-1 and (R)-2″-methoxyaceta
- Gill, Iqbal I.,Das, Jagbandhu,Patel, Ramesh N.
-
-
Read Online
- n-Butylamine as an alternative amine donor for the stereoselective biocatalytic transamination of ketones
-
Formal reductive amination has been a main focus of biocatalysis research in recent times. Among the enzymes able to perform this transformation, pyridoxal-5′-phosphate-dependent transaminases have shown the greatest promise in terms of extensive substrate scope and industrial application. Despite concerted research efforts in this area, there exist relatively few options regarding efficient amino donor co-substrates capable of allowing high conversion and atom efficiency with stable enzyme systems. Herein we describe the implementation of the recently described spuC gene, coding for a putrescine transaminase, exploiting its unusual amine donor tolerance to allow use of inexpensive and readily-available n-butylamine as an alternative to traditional methods. Via the integration of SpuC homologues with tandem co-product removal and cofactor regeneration enzymes, high conversion could be achieved with just 1.5 equivalents of the amine with products displaying excellent enantiopurity.
- Slabu, Iustina,Galman, James L.,Iglesias, Cesar,Weise, Nicholas J.,Lloyd, Richard C.,Turner, Nicholas J.
-
-
- Biocatalytic transamination with near-stoichiometric inexpensive amine donors mediated by bifunctional mono- and di-amine transaminases
-
The discovery and characterisation of enzymes with both monoamine and diamine transaminase activity is reported, allowing conversion of a wide range of target ketone substrates with just a small excess of amine donor. The diamine co-substrates (putrescine, cadaverine or spermidine) are bio-derived and the enzyme system results in very little waste, making it a greener strategy for the production of valuable amine fine chemicals and pharmaceuticals.
- Galman, James L.,Slabu, Iustina,Weise, Nicholas J.,Iglesias, Cesar,Parmeggiani, Fabio,Lloyd, Richard C.,Turner, Nicholas J.
-
supporting information
p. 361 - 366
(2017/08/14)
-
- PROCESS FOR THE PREPARATION OF CHIRAL AMINES BY ASYMMETRIC HYDROGENATION OF PROCHIRAL OXIMES
-
There is provided a method for the preparation of an enantiomerically enriched amine by asymmetric hydrogenation of a prochiral oxime.
- -
-
Page/Page column 5-7
(2015/12/08)
-
- PROCESS FOR THE PREPARATION OF CHIRAL AMINES FROM PROCHIRAL KETONES
-
There is provided a method for the preparation of an enantiomerically enriched amine from a prochiral ketone.
- -
-
Page/Page column 5; 6; 7
(2015/12/11)
-
- Transaminases applied to the synthesis of high added-value enantiopure amines
-
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
-
supporting information
p. 788 - 792
(2014/07/08)
-
- Organocatalytic asymmetric biomimetic transamination of aromatic ketone to optically active amine
-
An asymmetric biomimetic transamination of aromatic ketones to optically active amines with o-HOPhCH2NH2 as amine source catalyzed by hydroquinine-derived chiral base is described. Up to 85% ee was obtained.
- Xie, Ying,Pan, Hongjie,Xiao, Xiao,Li, Songlei,Shi, Yian
-
supporting information
p. 8960 - 8962,3
(2012/12/12)
-
- Organocatalytic asymmetric biomimetic transamination of aromatic ketone to optically active amine
-
An asymmetric biomimetic transamination of aromatic ketones to optically active amines with o-HOPhCH2NH2 as amine source catalyzed by hydroquinine-derived chiral base is described. Up to 85% ee was obtained.
- Xie, Ying,Pan, Hongjie,Xiao, Xiao,Li, Songlei,Shi, Yian
-
supporting information
p. 8960 - 8962
(2013/01/15)
-
- Synthesis of enantiomerically pure amino-substituted fused bicyclic rings
-
This invention describes various processes for synthesis and resolution of racemic amino-substituted fused bicyclic ring systems. One process utilizes selective hydrogenation of an amino-substituted fused bicyclic aromatic ring system. An alternative process prepares the racemic amino-substituted fused bicyclic ring system via nitrosation. In addition, the present invention describes the enzymatic resolution of a racemic mixture to produce the (R)- and (S)-forms of amino-substituted fused bicyclic rings as well as a racemization process to recycle the unpreferred enantioner. Further provided by this invention is an asymmetric synthesis of the (R)- or (S)-enantiomer of primary amino-substituted fused bicyclic ring systems.
- -
-
-
- Process for preparing optically active amines and optically active carboxylic acids, and intermediates for preparation
-
Disclosed is a process for preparing an optically active 1-aryl- or 2-aryl-alkylamines of formulas Ia, Ib and Ic with high optical purity and high yield. The process uses an optically active 1- or 2-naphthylglycolic acid of the general formula II as a resolving agent. Also disclosed is a process for praparing an optically active 1- or 2-naphthylglycolic acid of formula II using an optically active 1-aryl- or 2-aryl-alkylamines of formulas Ia, Ib and Ic as the resolving agents
- -
-
-
- Enantiomerically pure amines by a new method: Biotransformation of oxalamic esters using the lipase from Candida antarctica
-
Octyl oxalamic esters of 1-phenylethylamine and substituted 1-phenylethylamines are kinetically resolved with high stereoselectivity by lipase B from Candida antarctica.
- Chapman, Daniel T.,Crout, David H. G.,Mahmoudian, Mahmoud,Scopes, David I. C.,Smith, Paul W.
-
p. 2415 - 2416
(2007/10/03)
-
- A general enantioselective synthesis of α-arylethylamines
-
Optically active α-arylethylamines were prepared starting from acetophenones in ≥95%ee and ≥70% overall yield using oxazaborolidine catalyzed enantioselective reduction followed by the displacement of the hydroxy group by an azide group with clean inversion under Mitsunobu reaction conditions.
- Chen, Chung-Pin,Prasad, Kapa,Repic, Oljan
-
p. 7175 - 7178
(2007/10/02)
-