The DOI matches its Crossref record; 29 of the 29 references it cites were found in a registry or an index.
Diselenides and Allyl Selenides as Glutathione Peroxidase Mimetics. Remarkable Activity of Cyclic Seleninates Produced in Situ by the Oxidation of Allyl ω-Hydroxyalkyl Selenides
Abstract
A series of aliphatic diselenides and selenides containing coordinating substituents was tested for glutathione peroxidase (GPx)-like catalytic activity in a model system in which the reduction of tert-butyl hydroperoxide with benzyl thiol to afford dibenzyl disulfide and tert-butyl alcohol was performed under standard conditions and monitored by HPLC. Although the diselenides showed generally poor catalytic activity, allyl selenides proved more effective. In particular, allyl 3-hydroxypropyl selenide (25) rapidly generated 1,2-oxaselenolane Se-oxide (31) in situ by a series of oxidation and [2,3]sigmatropic rearrangement steps. The remarkably active cyclic seleninate 31 proved to be the true catalyst, reacting with the thiol via a postulated mechanism in which the thioseleninate 32 is first produced, followed by further thiolysis to selenenic acid 33 and oxidation-dehydration to regenerate 31. In contrast to catalysis with GPx, formation of the corresponding selenenyl sulfide 34 comprises a competing deactivation pathway in the catalytic cycle of 31, as a separate experiment revealed that authentic 34 was a much less effective catalyst than 31. 1,2-Oxaselenane Se-oxide (37), the six-membered homologue of 31, was formed similarly from allyl 4-hydroxybutyl selenide (26), but proved a less effective catalyst than 31. Compounds 31 and 37 are the first examples of unsubstituted monocyclic seleninate esters.
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
Cites
Chemistry of Biologically Important Synthetic Organoselenium Compounds
Mugesh, G., du Mont, W.-W., & Sies, H. (2001) · Chemical Reviews · doi:10.1021/cr000426w · Cited by 1,689
A novel biologically active seleno-organic compound—1
Müller, A., Cadenas, E., Graf, P., & Sies, H. (1984) · Biochemical Pharmacology · doi:10.1016/0006-2952(84)90083-2 · Cited by 828
The Refined Structure of the Selenoenzyme Glutathione Peroxidase at 0.2‐nm Resolution
EPP, O., LADENSTEIN, R., & WENDEL, A. (1983) · European Journal of Biochemistry · doi:10.1111/j.1432-1033.1983.tb07429.x · Cited by 689
A novel biologically active seleno-organic compound—II
Wendel, A., Fausel, M., Safayhi, H., Tiegs, G., & Otter, R. (1984) · Biochemical Pharmacology · doi:10.1016/0006-2952(84)90084-4 · Cited by 433
Development of synthetic compounds with glutathione peroxidase activity
Wilson, S. R., Zucker, P. A., Huang, R. R. C., & Spector, A. (1989) · Journal of the American Chemical Society · doi:10.1021/ja00197a065 · Cited by 413
(1965) · Physics Today · doi:10.1063/1.3047206 · Cited by 412
A Model Study on the Effect of an Amino Group on the Antioxidant Activity of Glutathione Peroxidase
Iwaoka, M., & Tomoda, S. (1994) · Journal of the American Chemical Society · doi:10.1021/ja00085a040 · Cited by 357
Glutathione Peroxidase-like Antioxidant Activity of Diaryl Diselenides: A Mechanistic Study
Mugesh, G., Panda, A., Singh, H. B., Punekar, N. S., & Butcher, R. J. (2001) · Journal of the American Chemical Society · doi:10.1021/ja994467p · Cited by 348
Selenosubtilisin as a glutathione peroxidase mimic
Wu, Z. P., & Hilvert, D. (1990) · Journal of the American Chemical Society · doi:10.1021/ja00170a043 · Cited by 247
Biosynthesis and function of selenocysteine-containing enzymes.
Stadtman, T. C. (1991) · Journal of Biological Chemistry · doi:10.1016/s0021-9258(18)55285-6 · Cited by 209
Thiol peroxidase activity of diaryl ditellurides as determined by a proton NMR method
Engman, L., Stern, D., Cotgreave, I. A., & Andersson, C. M. (1992) · Journal of the American Chemical Society · doi:10.1021/ja00051a002 · Cited by 187
A Novel Camphor-Derived Selenenamide That Acts as a Glutathione Peroxidase Mimetic
Back, T. G., & Dyck, B. P. (1997) · Journal of the American Chemical Society · doi:10.1021/ja963602k · Cited by 185
Self-citationOrganoselenium chemistry. Redox chemistry of selenocysteine model systems
Reich, H. J., & Jasperse, C. P. (1987) · Journal of the American Chemical Society · doi:10.1021/ja00252a055 · Cited by 174
Mugesh, G., & Μοnt, W.-W. D. (2001) · Chemistry - A European Journal · doi:10.1002/1521-3765(20010401)7:7<1365::aid-chem1365>3.0.co;2-y · Cited by 153
Back, T. G., & Moussa, Z. (2002) · Journal of the American Chemical Society · doi:10.1021/ja028030k · Cited by 150
Self-citationMechanism of the Catalytic Reduction of Hydroperoxides by Ebselen : A Selenium ‐ 77 Nmr Study
Fischer, H., & Dereu, N. L. M. (1987) · Bulletin des Sociétés Chimiques Belges · doi:10.1002/bscb.19870961006 · Cited by 148
A novel biologically active seleno-organic compound—III
Parnham, M. J., & Kindt, S. (1984) · Biochemical Pharmacology · doi:10.1016/0006-2952(84)90085-6 · Cited by 142
Flohé, L. (1985) · Current topics in cellular regulation · doi:10.1016/b978-0-12-152827-0.50047-5 · Cited by 129
Haenen, G. R. M. M., de Rooij, B. M., Vermeulen, N. P. E., & Bast, A. (1990) · Molecular Pharmacology · doi:10.1016/s0026-895x(25)10816-x · Cited by 114
Glutathione Peroxidase-like Activities of Oxygen-Containing Diselenides
Wirth, T. (1998) · Molecules · doi:10.3390/30700164 · Cited by 114
Diferrocenyl diselenides: excellent thiol peroxidase-like antioxidants
Mugesh, G., Panda, A., Singh, H. B., Punekar, N. S., & Butcher, R. J. (1998) · Chemical Communications · doi:10.1039/a805941a · Cited by 112
A novel biologically active seleno-organic compound—VI
Wendel, A., & Tiegs, G. (1986) · Biochemical Pharmacology · doi:10.1016/0006-2952(86)90578-2 · Cited by 109
Galet, V., Bernier, J., Henichart, J. P., Lesieur, D., Abadie, C., Rochette, L., Lindenbaum, A., Chalas, J., & Faverie, J.-F. R. D. L. (1994) · Journal of Medicinal Chemistry · doi:10.1021/jm00044a011 · Cited by 107
Selenium–Glutathione Peroxidase: Properties and Synthesis
Tappel, A. L. (1984) · Current topics in cellular regulation · doi:10.1016/b978-0-12-152824-9.50015-0 · Cited by 96
Jacquemin, P., Christiaens, L., Renson, M. J., Evers, M. J., & Dereu, N. L. M. (1992) · Tetrahedron Letters · doi:10.1016/s0040-4039(00)74805-2 · Cited by 87
Structural characterization of selenosubtilisin by selenium-77 NMR spectroscopy
House, K. L., Dunlap, R. B., Odom, J. D., et al. (1992) · Journal of the American Chemical Society · doi:10.1021/ja00048a033 · Cited by 87
Kice, J. L., & Lee, T. W. S. (1978) · Journal of the American Chemical Society · doi:10.1021/ja00484a031 · Cited by 83
Goto, K., Nagahama, M., Mizushima, T., et al. (2001) · Organic Letters · doi:10.1021/ol016682s · Cited by 73
Biochemical Aspects of Selenium Amino Acids and Selenium Peptides
Soda, K. (1992) · Phosphorus, sulfur, and silicon and the related elements · doi:10.1080/10426509208045872 · Cited by 13
Cited by
Toxicology and pharmacology of selenium: emphasis on synthetic organoselenium compounds
Nogueira, C. W., & Rocha, J. B. T. (2011) · Archives of Toxicology · doi:10.1007/s00204-011-0720-3 · Cited by 477
Mugesh, G. (2013) · Current Chemical Biology · doi:10.2174/2212796811307010005 · Cited by 39
Metadata
- Authors
- Back, T. G., & Moussa, Z.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2003-10-08
- Volume
- 125
- Issue
- 44
- Pages
- 13455-13460
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2039406638
- Cited by
- 254
- References
- 29
- FWCI
- 13.21
- 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
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.
