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(Reference retrieved automatically from Web of Science through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

Synthesis of 2,5-Disubstituted Pyrrolidine Alkaloids via A One-Pot Cascade Using Transaminase and Reductive Aminase Biocatalysts

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Author(s):
Costa, Bruna Z. [1, 2] ; Galman, James L. [1] ; Slabu, Iustina [1] ; France, Scott P. [1] ; Marsaioli, Anita J. [2] ; Turner, Nicholas J. [1]
Total Authors: 6
Affiliation:
[1] Univ Manchester, Manchester Inst Biotechnol, Sch Chem, 131 Princess St, Manchester M1 7DN, Lancs - England
[2] Univ Estadual Campinas, Chem Inst, Rua Monteiro Lobato 277, BR-13083970 Campinas, SP - Brazil
Total Affiliations: 2
Document type: Journal article
Source: CHEMCATCHEM; v. 10, n. 20, p. 4733-4738, OCT 23 2018.
Web of Science Citations: 6
Abstract

A multi-enzymatic cascade process involving transaminases (TAs) and reductive aminases (RedAms) to produce enantiomerically pure 2,5-disubstituted pyrrolidine alkaloids from their respective 1,4-diketones is reported. Several TAs were screened and the best results for diketone monoamination were obtained with an R-selective TA from Mycobacterium chlorophenicum and with an S-selective TA from Bacillus megaterium. Pyrroline reduction was best performed by a reductive aminase from Ajellomyces dermatitidis (AdRedAm). Finally, a biocatalytic one-pot cascade was implemented using the aforementioned enzymes and a variety of 2-methyl-5-alkylpyrrolidines were produced with high (>99%) conversion, diastereomeric and enantiomeric excess values. (AU)

FAPESP's process: 15/22513-5 - Biocatalytic processes involving transaminases and imine reductases for the synthesis of ant venom alkaloids.
Grantee:Bruna Zucoloto da Costa
Support Opportunities: Scholarships abroad - Research Internship - Post-doctor
FAPESP's process: 14/22967-3 - Piperidine and Pyrrolidine Alkaloids Synthesis in Multi-enzymatic systems
Grantee:Bruna Zucoloto da Costa
Support Opportunities: Scholarships in Brazil - Post-Doctoral
FAPESP's process: 14/50249-8 - Green chemistry: sustainable synthetic methods employing benign solvents, safer reagents, and bio-renewable feedstock
Grantee:Arlene Gonçalves Corrêa
Support Opportunities: Research Grants - Research Centers in Engineering Program