41051-72-3Relevant articles and documents
Biotransformation of [12C]- and [13C]-tert-amyl methyl ether and tert-amyl alcohol
Amberg, Alexander,Bernauer, Ulrike,Scheutzow, Dieter,Dekant, Wolfgang
, p. 958 - 964 (1999)
tert-Amyl methyl ether (TAME) is intended for use as a gasoline additive to increase oxygen content. Increased oxygen content in gasoline reduces tailpipe emissions of hydrocarbons and carbon monoxide from cars. Due to possible widespread use of TAME, the toxicity of TAME is under investigation. We studied the biotransformation of TAME in rats and one human volunteer after inhalation of 12C- or 13C-labeled TAME. In addition, the biotransformation of [13C]-tert-amyl alcohol was studied in rats after gavage. Urinary metabolites were identified by GC/MS and 13C NMR. Rats (two males and two females) were individually exposed to 2000 ppm [12C]- or [13C]TAME for 6 h, and urine was collected for 48 h. Free and glucuronidated 2-methyl-2,3-butanediol and a glucuronide of tert-amyl alcohol were identified by 13C NMR, GC/MS, and LC/MS/MS as major urinary metabolites on the basis of the relative intensities of the 13C NMR signals. The presence of several minor metabolites was also indicated by 13C NMR; they were identified as tert-amyl alcohol, 2-hydroxy-2- methylbutyric acid, and 3-hydroxy-3-methylbutyric acid. One human volunteer was exposed to an initial concentration of 27 000 ppm [13C]TAME by inhalation for 4 min from a 2 L gas sampling bag, and metabolites of TAME excreted in urine were analyzed by 13C NMR. All TAME metabolites identified in rats were also present in the human urine samples. To study tert-amyl alcohol biotransformation, male rats (n = 3) were treated with 250 mg/kg [13C]-tert-amyl alcohol dissolved in corn oil by garage, and urine was collected for 48 h. 13C NMR of the urine samples showed the presence of metabolites identical to those in the urine of [13C]TAME-treated rats. Our results suggest that TAME is extensively metabolized by rats and humans to tert-amyl alcohol which may be further oxidized to diols and carboxylic acids. These reactions are likely mediated by cytochrome P450-dependent oxidations.
Total synthesis and absolute configuration of avenolide, extracellular factor in Streptomyces avermitilis
Uchida, Miho,Takamatsu, Satoshi,Arima, Shiho,Miyamoto, Kiyoko T,Kitani, Shigeru,Nihira, Takuya,Ikeda, Haruo,Nagamitsu, Tohru
experimental part, p. 781 - 787 (2012/06/16)
The first total synthesis of extracellular factor, Avenolide, in Streptomyces avermitilis has been achieved using a convergent approach. The stereogenic centers in two key segments were installed using Sharpless epoxidation and dihydroxylation. This synthetic study allowed the determination of the absolute configuration of avenolide as 4S,10R, and yielded important information on its structure-activity relationship.
The absolute configuration of cuauhtemone and related compounds
Torres-Valencia, J. Martin,Quintero-Mogica, Dora L.,Leon, Guadalupe I.,Suarez-Castillo, Oscar R.,Villagomez-Ibarra, J. Roberto,Maldonado, Emma,Cerda-Garcia-Rojas, Carlos M.,Joseph-Nathan, Pedro
, p. 543 - 548 (2007/10/03)
The absolute configuration of cuauhtemone, a eudesmane-type sesquiterpene isolated from Pluchea species (Asteraceae), has been revised from 1 to 2 by chemical correlation with (R)-(+)-2-methyl-1,2-butanediol 3 through the naturally occurring 2,3-epoxy-2-methylbutanoate derivative 4. The relative stereochemistry of 4 was confirmed by X-ray diffraction analysis. The obtained data are also useful for reconsideration of the absolute configurations of a relevant group of natural products, which were elucidated according to the stereochemistry of cuauhtemone.