Transaminase-mediated synthesis of enantiopure drug-like 1-(3′,4′-disubstituted phenyl)propan-2-amines?
RSC Advances Pub Date: 2020-11-10 DOI: 10.1039/D0RA08134E
Abstract
Transaminases (TAs) offer an environmentally and economically attractive method for the direct synthesis of pharmaceutically relevant disubstituted 1-phenylpropan-2-amine derivatives starting from prochiral ketones. In this work, we report the application of immobilised whole-cell biocatalysts with (R)-transaminase activity for the synthesis of novel disubstituted 1-phenylpropan-2-amines. After optimisation of the asymmetric synthesis, the (R)-enantiomers could be produced with 88–89% conversion and >99% ee, while the (S)-enantiomers could be selectively obtained as the unreacted fraction of the corresponding racemic amines in kinetic resolution with >48% conversion and >95% ee.
Recommended Literature
- [1] An approach towards the synthesis of novel fused nitrogen tricyclic heterocyclic scaffolds via GBB reaction? Sandip Gangadhar Balwe,Yeon Tae JeongOrg. Biomol. Chem., 2018,16, 1287-1296 10.1039/C7OB02933K
- [2] An anti-ultrasonic-stripping effect in confined micro/nanoscale cavities and its applications for efficient multiscale metallic patterning? Quan Xiang,Yiqin Chen,Zhiqin Li,Kaixi Bi,Guanhua Zhang,Huigao DuanNanoscale, 2016,8, 19541-19550 10.1039/C6NR07585A
- [3] An artificial CO-releasing metalloprotein built by histidine-selective metallation? Inês S. Albuquerque,Hélia F. Jeremias,Miguel Chaves-Ferreira,Dijana Matak-Vinkovic,Omar Boutureira,Carlos C. Rom?oChem. Commun., 2015,51, 3993-3996 10.1039/C4CC10204E
- [4] An Appraisal of pH triggered Bacitracin drug release, through composite hydrogel systems RabailGul,MariamMir,MurtazaNAli 10.1177/08853282231160212
- [5] An atmosphere and light tuned highly diastereoselective synthesis of cyclobuta/penta[b]indoles from aniline-tethered alkylidenecyclopropanes with alkynes? Bo Cao,Yin WeiChem. Commun., 2018,54, 2870-2873 10.1039/C8CC00180D
- [6] An anti-leakage liquid metal thermal interface material Kaiyuan Huang,Wangkang Qiu,Meilian Ou,Xiaorui Liu,Zenan Liao,Sheng ChuRSC Adv., 2020,10, 18824-18829 10.1039/D0RA02351E
- [7] An asymmetric supercapacitor based on controllable WO3 nanorod bundle and alfalfa-derived porous carbon? Kanjun Sun,Fengting Hua,Shuzhen Cui,Yanrong Zhu,Hui Peng,Guofu MaRSC Adv., 2021,11, 37631-37642 10.1039/D1RA04788D
- [8] Alternative mixtures to R-600a. Theoretical assessment and experimental energy evaluation of binary mixtures in a commercial cooler: Mélanges alternatifs au R-600a. évaluation théorique et évaluation énergétique expérimentale de mélanges binaires dans un refroidisseur commercial. DanielCalleja-Anta,DanielSánchez,LauraNebot-Andres,RamónCabello,RodrigoLlopis 10.1016/j.ijrefrig.2023.05.009
- [9] An assay for the enzyme N-acetyl-β-d-glucosaminidase (NAGase) based on electrochemical detection using screen-printed carbon electrodes (SPCEs) R. M. Pemberton,J. P. Hart,T. T. MottramAnalyst, 2001,126, 1866-1871 10.1039/B104874K
- [10] An integrated chip for immunofluorescence and its application to analyze lysosomal storage disorders Jie Shen,Ying Zhou,Tu Lu,Junya Peng,Zhixiang Lin,Yuhong Pang,Li YuLab Chip, 2012,12, 317-324 10.1039/C1LC20845D
Journal Name：RSC Advances
research_products
-
CAS no.: 89640-58-4
![1,2,3,4,5,6-Hexahydro-[2,3]bipyridinyl-6-ol](https://ossimg.kuujia.com/scimg/1271000/1270529-38-8x500.png)
![N-(3-cyanothiolan-3-yl)-2-[(2,2,2-trifluoroethyl)sulfanyl]pyridine-4-carboxamide](https://ossimg.kuujia.com/scimg/1444500/1444113-98-7x500.png)
![2,2-Difluoro-3-[methyl(2-methylbutyl)amino]propanoic acid](https://ossimg.kuujia.com/scimg/2138500/2138166-62-6x500.png)
![2-(1H-indol-3-yl)-N-{[6-(thiophen-2-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl]methyl}acetamide](https://ossimg.kuujia.com/scimg/2034500/2034271-14-0x500.png)