Spectral and chemical properties of dimethyldioxirane as determined by experiment and ab initio calculations

Adam, Waldemar; Chan, Yuk Yee; Cremer, Dieter; Gauss, Juergen; Scheutzow, Dieter; Schindler, Michael

doi:10.1021/jo00389a029

Cited by 272 publications

(163 citation statements)

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“…Dimethyldioxirane (DMDO) is the simplest form of dioxirane. This reagent is not commercially available due to instability during transport and storage but it can be prepared by reacting acetone and the triple salt Oxone ® (2KHSO 5 ·KHSO 4 ·K 2 SO 4 ) in the laboratory, both on small and large scales (Adam et al, 1987). Adam et al (1989) suggested that pH control between 7.0 and 7.5 by means of phosphate or bicarbonate buffer is essential for in-situ generation of dioxirane as low pH will suppress the critical deprotonation step (from 2 to 3, Scheme 5).…”

Section: Dioxiranesmentioning

confidence: 99%

Modification of olefinic double bonds of unsaturated fatty acids and other vegetable oil derivatives via epoxidation: A review

et al. 2017

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SUMMARY:The highly strained ring in epoxides makes these compounds very versatile intermediates. Epoxidized vegetable oils are gaining a lot of attention as renewable and environmentally friendly feedstock with various industrial applications such as plasticizers, lubricant base oils, surfactants, etc. Numerous papers have been published on the development of the epoxidation methods and the number is still growing. This review reports the synthetic approaches and applications of epoxidized vegetable oils. KEYWORDS: Epoxidation; Renewable feedstock; Unsaturated fatty acids; Vegetable Oils RESUMEN:Modificación del doble enlace olefínico en ácidos grasos insaturados y en derivados de aceites vegetales via epoxidación: Revisión. La alta tensión del anillo en los epóxidos hace que estos compuestos intermediarios sean muy versátiles. Los aceites vegetales epoxidados están ganando mucha atención como materia prima renovable y respetuosa con el medio ambiente con diversas aplicaciones industriales, tales como plastificantes, aceites base para lubricantes, tensioactivos, etc. Por esta razón, se han publicado numerosos trabajos sobre el desarrollo de métodos de epoxidación y el número todavía es creciente. Esta revisión aporta información sobre enfoques sintéticos y aplicaciones de aceites vegetales epoxidados.

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Section: Dioxiranesmentioning

confidence: 99%

Modification of olefinic double bonds of unsaturated fatty acids and other vegetable oil derivatives via epoxidation: A review

et al. 2017

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“…In order to obtain only one epoxide, dihydrozamoranic acid methyl ester (1a) was treated with dimethyldioxirane [23], giving selectively only compound 29α in 45% yield and producing the oxidation of the primary alcohol into the acid at C-15; following the same sequence as in Scheme 6 only compound 14 was obtained. …”

Section: Route Bmentioning

confidence: 99%

From Labdanes to Drimanes. Degradation of the Side Chain of Dihydrozamoranic Acid.

et al. 2004

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“…AFB-N 7 -Gua and 8,9-dihydro-8-(2,6-diamino-4-oxo-3,4-dihydropyrimid-5-yl formamido)-9-hydroxy-AFB (AFB-FAPyr) were synthesized by reaction of calf thymus DNA with chemically synthesized AFB-8,9-epoxide, which was prepared by the reaction of AFB with dimethyldioxirane as described by Baertschi et al (2). The oxidant dimethyldioxirane was synthesized as described by Murray and Jeyaraman (20) and Adam et al (1). AFB-8,9-epoxide-modified DNA was ethanol precipitated, washed, dried, and resuspended in water.…”

Section: Methodsmentioning

confidence: 99%

Development of Aflatoxin B ₁ -Lysine Adduct Monoclonal Antibody for Human Exposure Studies

Wang

Abubaker

et al. 2001

Appl Environ Microbiol

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Mouse monoclonal antibodies were developed against a synthetic aflatoxin B 1 (AFB)-lysine-cationized bovine serum albumin conjugate. The isotype of one of these antibodies, IIA4B3, has been classified as immunoglobulin G1(). The affinity and specificity of IIA4B3 were further characterized by a competitive radioimmunoassay. The affinities of IIA4B3 for AFB and its associated adducts and metabolites are ranked as follows: AFB-lysine > 8,9-dihydro-8-(2,6-diamino-4-oxo-3,4-dihydropyrimid-5-yl formamido)-9-hydroxy-AFB > AFB ‫؍‬ 8,9-dihydro-8-(N 7 -guanyl)-9-hydroxy-AFB > aflatoxin M 1 > aflatoxin Q 1 . IIA4B3 had about a 10-fold higher affinity for binding to AFB-lysine adduct than to AFB when 3 H-AFB-lysine was used as the tracer. The concentration for 50% inhibition for AFB-lysine was 0.610 pmol; that for AFB was 6.85 pmol. IIA4B3 had affinities at least sevenfold and twofold higher than those of 2B11, a previously developed antibody against parent AFB, for the major aflatoxin-DNA adducts 8,9-dihydro-8-(N 7 -guanyl)-9-hydroxy-AFB and 8,9-dihydro-8-(2,6-diamino-4-oxo-3,4-dihydropyrimid-5-yl formamido)-9-hydroxy-AFB, respectively. An analytical method based on a competitive radioimmunoassay with IIA4B3 and 3 H-AFB-lysine was validated with a limit of detection of 10 fmol of AFB-lysine adduct. The method has been applied to the measurement of AFB-albumin adduct levels in human serum samples collected from the residents of areas at high risk for liver cancer. Aflatoxins (AF), mainly produced by Aspergillus flavus andA. parasiticus, are a group of naturally occurring fungal metabolites that have long been recognized as significant environmental contaminants (17, 28). Aflatoxin B 1 (AFB), the most common mycotoxin found in human food and animal feed, is a potent hepatotoxic and genotoxic agent which has been listed as a known human carcinogen (group I) (6,17,28,29). Exposure to dietary AFB is one of the major risk factors in the etiology of human hepatocellular carcinoma in several regions of Africa and Southeast Asia (6,15,17,28,29,34). The development and application of highly sensitive and specific methods for detecting AFB and its associated metabolites and macromolecular adducts are critical for identifying individuals at high risk (13).The molecular biomarkers currently used in human and animal exposure studies are AFB metabolites and AFB macromolecular adducts, such as aflatoxin M 1 (AFM 1 ) and AFB-N 7 -guanine (AFB-N 7 -Gua), in urine and AFB-albumin adducts in serum (12,13,21,22,30). The use of AFB-albumin adducts as biomarkers is important because their estimated longer in vivo half-life compared to that of urinary metabolites may reflect integrated exposures over longer time periods (13,27). From a practical perspective pertinent to epidemiological studies, the measurement of serum AFB-albumin adduct levels offers a rapid, facile approach that can be used to screen very large numbers of people. Data from human exposure studies have also demonstrated that the excretion of urinary AFB-N 7 -Gua and the formatio...

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Spectral and chemical properties of dimethyldioxirane as determined by experiment and ab initio calculations

Cited by 272 publications

References 0 publications

Modification of olefinic double bonds of unsaturated fatty acids and other vegetable oil derivatives via epoxidation: A review

Modification of olefinic double bonds of unsaturated fatty acids and other vegetable oil derivatives via epoxidation: A review

From Labdanes to Drimanes. Degradation of the Side Chain of Dihydrozamoranic Acid.

Development of Aflatoxin B ₁ -Lysine Adduct Monoclonal Antibody for Human Exposure Studies

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Spectral and chemical properties of dimethyldioxirane as determined by experiment and ab initio calculations

Cited by 272 publications

References 0 publications

Modification of olefinic double bonds of unsaturated fatty acids and other vegetable oil derivatives via epoxidation: A review

Modification of olefinic double bonds of unsaturated fatty acids and other vegetable oil derivatives via epoxidation: A review

From Labdanes to Drimanes. Degradation of the Side Chain of Dihydrozamoranic Acid.

Development of Aflatoxin B 1 -Lysine Adduct Monoclonal Antibody for Human Exposure Studies

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Development of Aflatoxin B ₁ -Lysine Adduct Monoclonal Antibody for Human Exposure Studies