5077-67-8Relevant articles and documents
Oxidation of but-3-en-1,2-diol: Green access to hydroxymethionine intermediate
Grasset,Rey,Bellière-Baca,Araque,Paul,Dumeignil,Wojcieszak,Katryniok
, p. 164 - 167 (2017)
Supported metallic and bimetallic systems were used for the selective oxidation of but-3-en-1,2-ol (BDO) to hydroxybut-3-en-2-one (HBO), an intermediate in the hydroxymethionine synthesis. All catalysts were active in this reaction. However, bimetallic systems were found more active and selective to HBO in the liquid aqueous phase at 50 °C using molecular O2 as a benign oxidant. The best performance (87% BDO conversion and 88% HBO selectivity) was observed over a 2%PdPt/TiO2 catalyst. No metal leaching was observed under the conditions studied.
Oxidation of 3-butene-1,2-diol by alcohol dehydrogenase
Kemper, Raymond A.,Elfarra, Adnan A.
, p. 1127 - 1134 (1996)
3-Butene-1,2-diol(BDD)is a metabolite of the carcinogenic petrochemical 1,3-butadiene. BDD is produced by cytochrome P450-mediated oxidation of 1,3- butadiene to butadiene monoxide, followed by enzymatic hydrolysis by epoxide hydrolase. The metabolic disposition of BDD is unknown. The current work characterizes BDD oxidation by purified horse liver alcohol dehydrogenase (ADH) and by cytosolic ADH from mouse, rat, and human liver. BDD is oxidized by purified horse liver ADH in a stereoselective manner, with (S)-BDD oxidized at approximately 7 times the rate of (R)-BDD. Attempts to detect and identify metabolites of BDD using purified horse liver ADH demonstrated formation of a single stable metabolite, 1-hydroxy-2-butanone (HBO). A second possible metabolite, 1-hydroxy-3-butene-2-one (HBONE), was tentatively identified by GC/MS, but HBONE formation could not be clearly attributed to BDD oxidation, possibly due to its rapid decomposition in the incubation mixture. Formation of HBO by ADH was dependent upon reaction time, protein concentration, substrate concentration, and the presence of NAD. Inclusion of GSH or 4-methylpyrazole in the incubation mixture resulted in inhibition of HBO formation. Based on these results and other lines of evidence, a mechanism is proposed for HBO formation involving generation of several potentially reactive intermediates which could contribute to toxicity of 1,3- butadiene in exposed individuals. Comparison of kinetics of BDD oxidation in rat, mouse, and human liver cytosol did not reveal significant differences in catalytic efficiency (V(max)/K(m)) between species. These results may contribute to a better understanding of 1,3-butadiene metabolism and toxicity.
Enantioselective Cascade Biocatalysis for Deracemization of Racemic β-Amino Alcohols to Enantiopure (S)-β-Amino Alcohols by Employing Cyclohexylamine Oxidase and ω-Transaminase
Zhang, Jian-Dong,Chang, Ya-Wen,Dong, Rui,Yang, Xiao-Xiao,Gao, Li-Li,Li, Jing,Huang, Shuang-Ping,Guo, Xing-Mei,Zhang, Chao-Feng,Chang, Hong-Hong
, p. 124 - 128 (2020/09/21)
Optically active β-amino alcohols are very useful chiral intermediates frequently used in the preparation of pharmaceutically active substances. Here, a novel cyclohexylamine oxidase (ArCHAO) was identified from the genome sequence of Arthrobacter sp. TYUT010-15 with the R-stereoselective deamination activity of β-amino alcohol. ArCHAO was cloned and successfully expressed in E. coli BL21, purified and characterized. Substrate-specific analysis revealed that ArCHAO has high activity (4.15 to 6.34 U mg?1 protein) and excellent enantioselectivity toward the tested β-amino alcohols. By using purified ArCHAO, a wide range of racemic β-amino alcohols were resolved, (S)-β-amino alcohols were obtained in >99 % ee. Deracemization of racemic β-amino alcohols was conducted by ArCHAO-catalyzed enantioselective deamination and transaminase-catalyzed enantioselective amination to afford (S)-β-amino alcohols in excellent conversion (78–94 %) and enantiomeric excess (>99 %). Preparative-scale deracemization was carried out with 50 mM (6.859 g L?1) racemic 2-amino-2-phenylethanol, (S)-2-amino-2-phenylethanol was obtained in 75 % isolated yield and >99 % ee.
A mechanism study on the efficient conversion of cellulose to acetol over Sn-Co catalysts with low Sn content
Liu, Xiaodong,Liu, Xiaohao,Ma, Longlong,Wang, Haiyong,Xiao, Tianci,Zhang, Ying
, p. 6579 - 6587 (2020/11/16)
Efficient conversion of renewable cellulose to high value-added C3 chemicals is a great challenge in the field of biomass valorization. In this work, we found that the combination of Co and Sn could significantly improve the efficiency of cellulose conversion to acetol. 54.4% yield of acetol and 66.6% total yield of C3 products were obtained when using 2%Sn-10%Co/SiO2 (2 wt% Sn content) as a catalyst. However, using the same Sn content of 2%Sn-10%Ni/SiO2, no acetol and only 7.1% yield of C3 products were produced. By studying the effects of different Sn and Co concentrations on cellulose conversion, it was found that the Sn species play an important role in catalyzing glucose conversion to C3 intermediates, while Co mainly played a role in hydrogenation, the same as Ni. The study demonstrated that Sn-Co/SiO2 with low Sn content can convert glucose to C3 intermediates more efficiently than the Sn-Ni/SiO2 catalyst. Moreover, Sn-Co/SiO2 could effectively convert C3 intermediates to acetol at a high temperature which is essential for acetol production from cellulose; but under the same conditions, the Sn-Ni/SiO2 catalyst tended to catalyze the polymerization of C3 intermediates. A series of characterization methods including AAS, TEM, HRTEM, EDS, XRD, ex situ XPS, in situ XPS, and CO2-TPD found that the combination of Sn and Co could significantly increase the noninteger valent SnOx species in the catalyst. These species increased the basicity of the catalyst and were beneficial in catalyzing the isomerization of glucose and the retro-aldol condensation of fructose. This journal is
