Ingrid C.R. Costa , Rodrigo Octavio M.A. de Souza , Uwe T. Bornscheuer
{"title":"Asymmetric synthesis of serinol-monoesters catalyzed by amine transaminases","authors":"Ingrid C.R. Costa , Rodrigo Octavio M.A. de Souza , Uwe T. Bornscheuer","doi":"10.1016/j.tetasy.2017.08.012","DOIUrl":null,"url":null,"abstract":"<div><p><span>The asymmetric synthesis<span> of serinol-derivatives was investigated employing different amine transaminases<span><span> as biocatalysts. Under the optimized conditions conversions up to 92% and excellent </span>enantiomeric excesses up to 99% ee were obtained providing access to both, the (</span></span></span><em>R</em>)- and (<em>S</em>)-configurations of the serinol-monoester (2-amino-3-hydroxypropyl hexanoate).</p></div>","PeriodicalId":22237,"journal":{"name":"Tetrahedron, asymmetry","volume":null,"pages":null},"PeriodicalIF":0.0000,"publicationDate":"2017-09-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1016/j.tetasy.2017.08.012","citationCount":"5","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Tetrahedron, asymmetry","FirstCategoryId":"1085","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0957416617303506","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"Chemistry","Score":null,"Total":0}
引用次数: 5
Abstract
The asymmetric synthesis of serinol-derivatives was investigated employing different amine transaminases as biocatalysts. Under the optimized conditions conversions up to 92% and excellent enantiomeric excesses up to 99% ee were obtained providing access to both, the (R)- and (S)-configurations of the serinol-monoester (2-amino-3-hydroxypropyl hexanoate).
期刊介绍:
Cessation. Tetrahedron: Asymmetry presents experimental or theoretical research results of outstanding significance and timeliness on asymmetry in organic, inorganic, organometallic and physical chemistry, as well as its application to related disciplines, especially bio-organic chemistry.
The journal publishes critical reviews, original research articles and preliminary communications dealing with all aspects of the chemical, physical and theoretical properties of non-racemic organic and inorganic materials and processes. Topics relevant to the journal include: the physico-chemical and biological properties of enantiomers; strategies and methodologies of asymmetric synthesis; resolution; chirality recognition and enhancement; analytical techniques for assessing enantiomeric purity and the unambiguous determination of absolute configuration; and molecular graphics and modelling methods for interpreting and predicting asymmetric phenomena. Papers describing the synthesis or properties of non-racemic molecules will be required to include a separate statement in the form of a Stereochemistry Abstract, for publication in the same issue, of the criteria used for the assignment of configuration and enantiomeric purity.