5933-40-4Relevant articles and documents
Synthesis of limonene β-amino alcohol from (R)-(+)-α-methylbenzylamine and (+)-limonene 1,2-epoxide
Ait Said, Lyazid,El Bachiri, Abdelhadi,El Haimer, Chaimaa,El Hammoumi, Mohamed Merouane,Khoukhi, Mostafa
, (2021/06/02)
Two new compounds of β-amino alcohol are obtained using (R) - (+) - α-methylbenzylamine as starting material which is converted into two amines. Each of these compounds reacted in excess with a 1: 1 mixture of cis and trans-limonene oxide in the presence of water as a catalyst. The products obtained show that β-amino alcohol derived from trans-limonene oxide is obtained and unreacted cis-limonene oxide from the reaction mixture as well as the amine is attained. Whereas the addition of the synthesized carbamate of the same primary amine over the 1: 1 mixture of cis and trans -limonene oxide in the presence of water results in the hydrolysis product and the recovery of unreacted trans-limonene oxide.
Screening and characterization of a diverse panel of metagenomic imine reductases for biocatalytic reductive amination
Marshall, James R.,Yao, Peiyuan,Montgomery, Sarah L.,Finnigan, James D.,Thorpe, Thomas W.,Palmer, Ryan B.,Mangas-Sanchez, Juan,Duncan, Richard A. M.,Heath, Rachel S.,Graham, Kirsty M.,Cook, Darren J.,Charnock, Simon J.,Turner, Nicholas J.
, p. 140 - 148 (2021/01/04)
Finding faster and simpler ways to screen protein sequence space to enable the identification of new biocatalysts for asymmetric synthesis remains both a challenge and a rate-limiting step in enzyme discovery. Biocatalytic strategies for the synthesis of chiral amines are increasingly attractive and include enzymatic asymmetric reductive amination, which offers an efficient route to many of these high-value compounds. Here we report the discovery of over 300 new imine reductases and the production of a large (384 enzymes) and sequence-diverse panel of imine reductases available for screening. We also report the development of a facile high-throughput screen to interrogate their activity. Through this approach we identified imine reductase biocatalysts capable of accepting structurally demanding ketones and amines, which include the preparative synthesis of N-substituted β-amino ester derivatives via a dynamic kinetic resolution process, with excellent yields and stereochemical purities. [Figure not available: see fulltext.]
Asymmetric Synthesis of Primary and Secondary β-Fluoro-arylamines using Reductive Aminases from Fungi
González-Martínez, Daniel,Cuetos, Aníbal,Sharma, Mahima,García-Ramos, Marina,Lavandera, Iván,Gotor-Fernández, Vicente,Grogan, Gideon
, p. 2421 - 2425 (2020/03/25)
The synthesis of chiral amines is of central importance to pharmaceutical chemistry, and the inclusion of fluorine atoms in drug molecules can both increase potency and slow metabolism. Optically enriched β-fluoroamines can be obtained by the kinetic resolution of racemic amines using amine transaminases (ATAs), but yields are limited to 50 %, and also secondary amines are not accessible. In order to overcome these limitations, we have applied NADPH-dependent reductive aminase enzymes (RedAms) from fungal species to the reductive amination of α-fluoroacetophenones with ammonia, methylamine and allylamine as donors, to yield β-fluoro primary or secondary amines with >90 % conversion and between 85 and 99 % ee. In addition, the effect of the progressive introduction of fluorine atoms to the α-position of the acetophenone substrate reveals the effect of mono-, di- and tri-fluorination on the proportion of amine and alcohol in product mixtures, shedding light on the promiscuous ability of imine reductase (IRED)-type dehydrogenases to reduce fluorinated acetophenones to alcohols.
