Metabolism of bile alcohols in the perfused rabbit liver - C26 bile alcohols

The metabolism of a C26 bile alcohol (I, 24-nor-5beta-cho-lestane-3alpha, 7alpha,25-triol) was studied in the isolated perfused rabbit liver. The new bile alcohol and bile acid metabolites secreted into the bile were isolated and identified by a combination of TLC, GLC and GLC-MS. The following bile alcohols were found: II, 24-nor-5beta-cholestane-3alpha,7alpha,12alpha,25-tetrol, III, 24-nor-5beta-cholestane-3alpha,7alpha,12alpha,25,26-pentol; IV, 24-nor-5beta-cholest-23-ene-3alpha,7alpha,12alpha-triol; and V, 24-nor-5beta-cholest-23-ene-3alpha,7alpha-diol. In the bile acid fraction, 24-nor-cholic acid and 3alpha,7alpha,12alpha-trihydroxy-24-nor-5beta-cholest-23-en-26-oic acid were present. The perfused nor-triol was not resistant to 12alpha-hydroxylation.     

Microbial electrode sensor for alcohols

A microbial electrode consisting of immobilized microorganisms, a gas permeable Teflon membrane, and an oxygen electrode was prepared for the continuous determination of methyl and ethyl alcohols. Immobilized Trichosporon brassicae was employed for a microbial electrode sensor for ethyl alcohol. When a sample solution containing ethyl alcohol was injected into a microbial electrode system, the current of the electrode decreased markedly with time until a steady state was reached. The response time was within 10 min by the steady state method and within 6 min by the pulse method. A linear relationship was observed between the current decrease and the concentration of ethyl alcohol below 22.5 mg/liter. The current was reproducible within ± 6% of the relative error when a sample solution containing 16.5 mg/liter ethyl alcohol. The standard deviation was 0.5 mg/liter in 40 experiments. The selectivity of the microbial electrode sensor for ethyl alcohol was satisfactory. The microbial electrode sensor was applied to a fermentation broth of yeasts and satisfactory comparative results were obtained (correlation coefficient 0.98). The current output of the microbial electrode sensor was almost constant for more than three weeks and 2100 assays. A microbial electrode sensor using immobilized bacteria for methyl alcohol was also described.     

Dihydrocinnamyl alcohols from Hortia badinii

Hortia badinii (Rutaceae) contains in the trunkwood skimmianine and 6,7-dimethoxycoumarin, as well as 3-[2-methoxy and 2,6-dimethoxy-6′,6′-dimethylpyrano (2′,3′:3,4)phenyl]-1-propanols.     

Interaction of alcohols with proteins

The kinetics of denaturation of egg albumin have been determined for methanol, ethanol, propanol, and butanol. The reactions are first order in respect to protein but between 11th and 18th order for the alcohols. The denaturation reaction is characterized by a large temperature coefficient with little or no dependence on pH. There is a marked change of pH when proteins are denatured. A series of eight proteins has been studied. There is surprisingly little difference in susceptibility to alcohol denaturation between the various proteins. Methanol, ethanol, propanol, and butanol are strongly bound to egg albumin—butanol being the most strongly bound. The binding of alcohol is probably accompanied by protein dehydration. The polyhydric alcohols' behavior is much different. These alcohols do not denature proteins and the protein is hydrated. Sucrose produces the greatest degree of hydration.     

Sesquiterpene alcohols from Artemisia pygmaea

Artemisia pygmaea Gray contains two sesquiterpene alcohols: the known cryptomeridiol (I) and pygmol (II), a new compound. No sesquiterpene lactones were found in the plant although other species of the section Tridentatae Rydb., with which A. pygmaea has been classified, are usually rich in lactones.     

Microbial production of fatty alcohols

Fatty alcohols have numerous commercial applications, including their use as lubricants, surfactants, solvents, emulsifiers, plasticizers, emollients, thickeners, and even fuels. Fatty alcohols are currently produced by catalytic hydrogenation of fatty acids from plant oils or animal fats. Microbial production of fatty alcohols may be a more direct and environmentally-friendly strategy since production is carried out by heterologous enzymes, called fatty acyl-CoA reductases, able to reduce different acyl-CoA molecules to their corresponding primary alcohols. Successful examples of metabolic engineering have been reported in Saccharomyces cerevisiae and Escherichia coli in which the production of fatty alcohols ranged from 1.2 to 1.9 g/L, respectively. Due to their metabolic advantages, oleaginous yeasts are considered the best hosts for production of fatty acid-derived chemicals. Some of these species can naturally produce, under specific growth conditions, lipids at high titers (>50 g/L) and therefore provide large amounts of fatty acyl-CoAs or fatty acids as precursors. Very recently, taking advantage of such features, over 8 g/L of C₁₆–C₁₈ fatty alcohols have been produced in Rhodosporidium toruloides. In this review we summarize the different metabolic engineering strategies, hosts and cultivation conditions used to date. We also point out some future trends and challenges for the microbial production of fatty alcohols.     

Enzyme mediated resolution of alcohols

Summary The racemic cis and trans isomers 1a and 1b of 2-(4-methoxybenzyl)-1-cyclohexanol were subjects of an enzyme mediated resolution via esterification in organic solvents, in which the chiral esters 2a and 2b of the corresponding alcohols 4a and 4b, and the chiral alcohols 3a and 3b were obtained. The chemical yield and enantioselectivity of this enzymatic reaction have been found to depend mainly on (a) the structure of the substrate (cis or trans), (b) temperature, (c) the nature of the enzyme selected, and (d) the nature of the solvent.     

Interaction between flavins and alcohols

The effect of alcohols on the spectral properties of riboflavin derivatives in non-polar solvent was studied by various spectroscopic methods in order to support the view point that alcohol may directly interact with the isoalloxazine moiety of FAD and enhance the catalytic activity of D-amino acid oxidase (DAAO). The most likely association complex between alcohol and riboflavin is 1 : 1 stoichiometric complex through the 3-N imino and the 2-C carbonyl groups of the isoalloxazine ring and the hydroxyl group of alcohols. It appears that methanol has a larger association constant than any other alcohols, and the association constant decreases with the increase in carbon number and with the steric requirement of the alkyl group of alcohols.     

Production of long-chain alcohols by yeasts

Fourteen yeast strains from six genera were analysed for the presence of long-chain alcohols. Six strains from three genera contained long-chain alcohols, highest levels being found in Candida albicans. The alcohols were identified and determined by TLC, GLC and GLC-MS. The major long-chain alcohols synthesized by these organisms were saturated, primary alcohols with C14, C16 or C18 chain length. Unsaturated long-chain alcohols were not detected. In all strains that produced long-chain alcohols, the relative proportions were C16 greater than C18 greater than C14. Long-chain alcohol contents were higher in organisms from anaerobically, as compared with aerobically, grown cultures reaching about 650 micrograms (g dry wt organisms)-1 in stationary-phase cultures of C. albicans. In cultures of C. albicans, synthesis of long-chain alcohols occurred only after the end of exponential growth. The alcohols were predominantly present as free alcohols. The fatty-acyl chain-length profile of the triacylglycerol and to a lesser extent the sterol/wax ester fractions from C. albicans reflected that of the long-chain alcohols produced by this yeast.     

Synthesis of optically active aminooxy alcohols

Racemic secondary alcohols with an N-protected oxyamino function in the β-position were prepared by a base-catalyzed epoxide ring opening with N-hydroxyphthalimide or acetone oxime. The enantiomers were separated with a good selectivity by a lipase-catalyzed acetylation of the racemates with vinyl acetate. The protecting group of the aminooxy alcohol was split off by a hydrochloric acid hydrolysis to yield the hydrochloride of one of the enantiomeric forms of the title compounds.     

高级醇的微生物绿色制造

高级醇是含有两个以上碳原子的醇类,具有比乙醇更优秀的燃料性能,是化石燃料的重要补充与替代品.利用微生物以可再生的生物质为原料进行高级醇的生产可同时缓解当前的能源与环境危机,已成为绿色生物制造的重大发展方向.天然的微生物仅能少量生产个别种类的高级醇,因此,通过代谢工程及合成生物学技术,在模式工业菌株中重构高级醇的合成途径...     

Secondary alcohols from Fragaria leaf waxes

The secondary alcohols isolated from Fragaria leaf waxes and characterised by GC-MS have been shown to be a mixture of isomers of hentriacontanol with the hydroxy substituent on carbons 9, 10, 11 and 12, and of tritriacontanol with the OH group in the 10, 11, 12, 13 and 14 positions, respectively.