2016
DOI: 10.1021/acscatal.6b00782
|View full text |Cite
|
Sign up to set email alerts
|

Stereoselectivity and Structural Characterization of an Imine Reductase (IRED) from Amycolatopsis orientalis

Abstract: The imine reductase AoIRED from Amycolatopsis orientalis (Uniprot R4SNK4) catalyzes the NADPH-dependent reduction of a wide range of prochiral imines and iminium ions, predominantly with (S)-selectivity and with e.e.s of up to >99%. AoIRED displays up to 100-fold greater catalytic efficiency for 2-methyl-1-pyrroline (2MPN) compared to other IREDs, such as the enzyme from Streptomyces sp. GF3546, which also exhibits (S)-selectivity, and thus AoIRED is an interesting candidate for preparative synthesis. AoIRED e… Show more

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...
1
1

Citation Types

8
146
0

Year Published

2016
2016
2022
2022

Publication Types

Select...
5
4

Relationship

4
5

Authors

Journals

citations
Cited by 107 publications
(154 citation statements)
references
References 41 publications
8
146
0
Order By: Relevance
“…[23] Unlike the situation for carbonyl-reducing enzymes, the catalytic residues and the reduction mechanism of IREDs are still under debate. [25] The recent investigations by Tawfik and co-workers on the evolution of the Rossmann-fold motif [26] and the structurals imilarity of IREDs to hydroxyisobutyratea nd b-hydroxyacidd ehydrogenases [8,11] strongly suggest ac ommona ncestry.D espite these common elements, IREDs and KREDs differ in their ability to reduce imines. [24] NADPH is considered the hydride donor,a lthough the proton-donating residue remains elusive.…”
mentioning
confidence: 99%
See 1 more Smart Citation
“…[23] Unlike the situation for carbonyl-reducing enzymes, the catalytic residues and the reduction mechanism of IREDs are still under debate. [25] The recent investigations by Tawfik and co-workers on the evolution of the Rossmann-fold motif [26] and the structurals imilarity of IREDs to hydroxyisobutyratea nd b-hydroxyacidd ehydrogenases [8,11] strongly suggest ac ommona ncestry.D espite these common elements, IREDs and KREDs differ in their ability to reduce imines. [24] NADPH is considered the hydride donor,a lthough the proton-donating residue remains elusive.…”
mentioning
confidence: 99%
“…Theoretically calculated activation energies encourage the speculation that imines are protonated prior to hydride transfer from NADPH. [10,20] Regarding speculations of the roles of amino acid residues for C=Np rotonation in IREDs, [11,25] there is some supporting evidenceb ased on mutations of putative catalytically important aspartic acid residues displaying reduced catalytic efficiencies over wild-type enzyme. This is in accordance with the work of Mayr and co-workers,w ho described the electrophilicity of benzaldehyde-derived iminium ions and their higherr eactivities compared to substituted imines.…”
mentioning
confidence: 99%
“…GF3587, S ‐IRED from Streptomyces sp . GF3546 and Ao IRED from Amycolatopsis orientalis . Biotransformations were initially performed in a whole‐cell system as it promotes in vivo cofactor regeneration by only supplementing the reaction medium with glucose.…”
Section: Resultsmentioning
confidence: 99%
“…Recently, Turner and co‐workers described the unexpected stereoselective patterns of an imine reductase from A. orientalis (AoIRED). In their case, AoIRED was shown to exhibit selectivity patterns that defy the Cahn‐Ingold‐Prelog priority rule . As enzymes displaying unusual selectivity properties emerge, further studies are required to uncover the mechanism for such unique behaviour.…”
Section: Engineering Of Isoprenoid Quinones Biosynthetic Enzymesmentioning
confidence: 99%