[reaction: see text]. 1,6:2,3-Dianhydrohexopyranoses (Cerny epoxides) are versatile intermediates for the synthesis of glycosaminoglycans. Complex heparan and chondroitin sulfate disaccharide synthons can be assembled from a single common precursor in a short sequence of steps.

The development of the homologous Julia-Kocienski reaction has led to the discovery of two new reaction modes of epoxides with sulfones. These pathways allow rapid and direct access to a range of γ-sultones and γ-sultines.

Rhodium-catalyzed transannulation of 1,2,3-triazoles and ring-opening reactions of epoxides is described. A number of 3,4-dihydro-2H-1,4-oxazines are obtained in moderate yields probably involving generation of α-imino rhodium(II) carbene species.

Six epoxides of structurally related chloroalkenes were examined for their carcinogenicity by chronic testing in female ICR/Ha Swiss mice, 30/group. Repeated skin application three times weekly or s.c. injection once weekly were used for the life spans of the mice. The epoxides were: cis-1-chloropropene oxide, trans-1-chloropropene oxide, cis-1,3-dichloropropene oxide, trans-1,3-dichloropropene...

Epoxide hydrolase hydrates epoxides to vicinal diols in the phyto-oxylipin peroxygenase pathway resulting in the production of epoxy alcohols, dihydrodiols, triols and epoxides, including many lipid epoxides associated with resistance. Two epoxide hydrolase genes from Nicotiana benthamiana L., NbEH1.1 and NbEH1.2, were amplified from codingDNAof leaves during a susceptible response to the hemib...

Polyols and sulfate esters have recently been identified in the secondary organic aerosol (SOA) formed in the photooxidation of biogenic hydrocarbons both in the laboratory and under ambient atmospheric conditions. In the present study, the potential role of the reactions of epoxides in SOA to form diols and hydroxy sulfate esters is explored. Nuclear magnetic resonance methods were used to mon...

A new method to determine epoxide concentrations in oxidized oils was developed and validated using (1)H NMR. Epoxides derived from lipid oxidation gave signals between 2.90 and 3.24 ppm, well separated from the signals of other lipid oxidation products. To calibrate, soybean oils with a range of epoxide concentrations were synthesized and analyzed using (1)H NMR by taking the sn-1,3 glycerol p...

Short-chain halogenated aliphatics, such as chlorinated ethenes, constitute a large group of priority pollutants. This paper gives an overview on the chemical and physical properties of chlorinated aliphatics that are critical in determining their toxicological characteristics and recalcitrance to biodegradation. The toxic effects and principle metabolic pathways of halogenated ethenes in mamma...

The mixed-function oxidases containing cytochrome P450 are the primary systems that metabolize xenobiotics including drugs and carcinogens and endogenous substrates such as steroids [l-3]. The mixed-function oxidases may be key determinants of the rates of drug metabolism [2] and carcinogen susceptibility [3-S]. A major class of carcinogens to which humans are exposed is the polycyclic aromatic...

Biological transformations of polyunsaturated fatty acids often lead to chemically unstable products, such as the prostaglandin endoperoxides and leukotriene A(4) epoxide of mammalian biology and the allene epoxides of plants. Here, we report on the enzymatic production of a fatty acid containing a highly strained bicyclic four-carbon ring, a moiety known previously only as a model compound for...