The DOI matches its Crossref record.
Asymmetric Bioreduction of CC Bonds using Enoate Reductases OPR1, OPR3 and YqjM: Enzyme‐Based Stereocontrol
Abstract
Three cloned enoate reductases from the “old yellow enzyme” family of flavoproteins were investigated in the asymmetric bioreduction of activated alkenes. 12‐Oxophytodienoate reductase isoenzymes OPR1 and OPR3 from Lycopersicon esculentum (tomato), and YqjM from Bacillus subtilis displayed a remarkably broad substrate spectrum by reducing α,β‐unsaturated aldehydes, ketones, maleimides and nitroalkenes. The reaction proceeded with absolute chemoselectivity – only the conjugated CC bond was reduced, while isolated olefins and carbonyl groups remained intact – with excellent stereoselectivities (ee s up to >99%). Upon reduction of a nitroalkene, the stereochemical outcome could be determined via choice of the appropriate enzyme (OPR1 versus OPR3 or YqjM), which furnished the corresponding enantiomeric nitroalkanes in excellent ee. Molecular modelling suggests that this “enzyme‐based stereocontrol” is caused by subtle differences within the active site geometries.
Overview
The claims and statistics of this paper haven’t been checked yet.
Run the check — free, no account needed. It reads the open-access text and checks the sources it cites.
Integrity signals
Registry
Cites
Statistics
Verification
Claims the paper makes
The claims and statistics of this paper haven’t been checked yet.
Run the check — free, no account needed. It reads the open-access text and checks the sources it cites.
Self-check
Percentages, sums and reported differences re-computed from the paper’s own numbers.
The self-check needs the paper’s full text.
Citations
Cited by
Enzymatic reductions for the chemist
Hollmann, F., Arends, I. W. C. E., & Holtmann, D. (2011) · Green Chemistry · doi:10.1039/c1gc15424a · Cited by 377
Photobiocatalytic Strategies for Organic Synthesis
Emmanuel, M. A., Bender, S. G., Bilodeau, C., Carceller, J. M., DeHovitz, J. S., Fu, H., Liu, Y., Nicholls, B. T., Ouyang, Y., Page, C. G., et al. (2023) · Chemical Reviews · doi:10.1021/acs.chemrev.2c00767 · Cited by 328
Wasternack, C., & Kombrink, E. (2010) · ACS Chemical Biology · doi:10.1021/cb900269u · Cited by 274
Grimm, H. C., Erlsbacher, P., Medipally, H., Malihan-Yap, L., Sovic, L., Zöhrer, J., Kosourov, S. N., Allahverdiyeva, Y., Paul, C. E., & Kourist, R. (2025) · Green Chemistry · doi:10.1039/d4gc05686h · Cited by 13
Metadata
- Authors
- Hall, M., Stueckler, C., Ehammer, H., Pointner, E., Oberdorfer, G., Gruber, K., Hauer, B., Stuermer, R., Kroutil, W., Macheroux, P., & Faber, K.
- Venue
- Advanced Synthesis & Catalysis
- Publisher
- Wiley
- Published
- 2008-02-19
- Volume
- 350
- Issue
- 3
- Pages
- 411-418
- ISSN
- 1615-4150 (ISSN-L)
- 1615-4169
- OpenAlex
- W1968449206
- Cited by
- 190
- References
- 0
- FWCI
- 7.32
- Type
- journal article
- Language
- en
- Open access
- closed
About these checks
Registry, retraction, Cites and statistics results are computed, not judged, with one exception: a printed reference that no index lists is read once by a model before it counts as a citation error. Claims are extracted by a model and kept only when their quote appears verbatim in the text; each cited source is then checked, with a model’s help, for whether it says what the claim relies on. Those verdicts can be wrong — read the claim’s quote and the cited source before relying on one.
Statistics and arithmetic are recomputed, not judged.
Confidence bands are shown only for fields calibrated on our annotated test set. None is calibrated yet, so no band is shown.
What counts as a claim ›How we measure confidence ›How we check this ›
Are you an author, or do you see a problem with this page? Request a review
How to cite
Cite CoChat for the checks on this page, and the paper for its own findings.
- This page
- CoChat. (2026). Citation check: Asymmetric Bioreduction of CC Bonds using Enoate Reductases OPR1, OPR3 and YqjM: Enzyme‐Based Stereocontrol. https://app.cochat.ai/papers/10.1002/adsc.200700458
- The paper
- Hall, M., Stueckler, C., Ehammer, H., Pointner, E., Oberdorfer, G., Gruber, K., Hauer, B., Stuermer, R., Kroutil, W., Macheroux, P., & Faber, K. (2008). Asymmetric Bioreduction of CC Bonds using Enoate Reductases OPR1, OPR3 and YqjM: Enzyme‐Based Stereocontrol. Advanced Synthesis & Catalysis. https://doi.org/10.1002/adsc.200700458
Data sources
Bibliographic data: Semantic Scholar, OpenAlex, Crossref.
Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).
Semantic Scholar’s data is described in: Kinney, R., et al. (2023). The Semantic Scholar Open Data Platform. arXiv:2301.10140.
