Tetrahedron | Date: 2017-04-05
The invention relates to a compound of the 5-acylsulfanyl-histidine type and the derivatives thereof, of general formula (I), wherein R1 to R3 = H, alkyl, especially CH3; R4 = H, alkyl, especially CH3, alkyle(C=0), substituted alkyl (C=O), aryl (C=O); -alanyl (H2NCH2CH2 (C=O); -amino-acyl; R5 = alkyl, especially methyl, phenyl. The invention also relates to the use of said compound for producing compounds of the 5-sulfanyl-histidine type and the derivatives thereof, in addition to corresponding disulfides; and to the various methods for the production thereof.
Tetrahedron | Date: 2017-07-26
The invention relates to a method for the purification of L-hercynine. Said method for the purification of L-hercynine, from a reaction mixture resulting from the reaction of L-histidine, in controlled pH conditions, with a methylating agent Me X in a polar solvent or a mixture of polar solvents, at room temperature, is characterised in that it comprises at least one step of separating the organic products from the inorganic salts formed during the reaction by electrodialysis. This method allows the L-hercynine losses to be limited during the purification.
Tetrahedron | Date: 2017-02-15
The invention relates to a selenium compound. Said selenium compound has formula (I), where R1 = alkyl; R2 = H, R4C(=0), R4OC(=0), a-aminoacyl, CH3SeCH2CH2CH(NH2)C(=0), CH3SeCH2CH2CH(OH)C(=0); X = OH, OR3, NH2, NR4R5, -amino acid, CH3SeCH2CH2CH(COOH)NH-, CH3SeCH2CH2CH(COOH)0-; R3 = alkyl; R4 = alkyl, aryl; R5 = H, alkyl, aryl; R4 and R5 which can together form a 5- or 6-membered cycloalkyl radical which can comprise a heteroatom; provided that when X = NH-terbutyl, R2 C(=0)CH3. Said compound can be used as a pharmaceutical substance, in particular as an anitumour ssubstance.
Tetrahedron | Date: 2015-04-07
The invention relates to a selenium compound. Said selenium compound has formula (I), where R^(1)=alkyl; R^(2)=H, R^(4)C(=0), R^(4)OC(=0), a-aminoacyl, CH_(3)SeCH_(2)CH_(2)CH(NH_(2))C(=0), CH_(3)SeCH_(2)CH_(2)CH(OH)C(=0); X=OH, OR^(3), NH_(2), NR^(4)R^(5), -amino acid, CH_(3)SeCH_(2)CH_(2)CH(COOH)NH, CH_(3)SeCH_(2)CH_(2)CH(COOH)0-; R^(3)=alkyl; R^(4)=alkyl, aryl; R^(5)=H, alkyl, aryl; R^(4 )and R^(5 )which can together form a 5- or 6-membered cycloalkyl radical which can comprise a heteroatom; provided that when X=NH-terbutyl, R^(2)C(=0)CH_(3). Said compound can be used as a pharmaceutical substance, in particular as an antitumour substance.
Vacchina V.,UT2A |
Moutet M.,Tetrahedron |
Yadan J.-C.,Tetrahedron |
de Baene F.,Eco Solution |
And 2 more authors.
Journal of Chromatography B: Analytical Technologies in the Biomedical and Life Sciences | Year: 2010
An analytical method was developed for the simultaneous speciation of selenomethionine (SeMet) and 2-hydroxy-4-methylselenobutanoic acid (NutraSelen®), a new SeMet precursor. The compounds could be baseline resolved by ion-pairing reversed-phase HPLC using ICP MS detection. Detection limits of 1 ng mL-1 (Se content) could be reached. SELM-1 reference material was used to validate the SeMet measurement. Additionally, the quantification of NutraSelen® was validated by standard addition together with checking the Se mass balance. The procedure developed was then applied to the monitoring of the conversion of NutraSelen® into SeMet by yeast. © 2010 Elsevier B.V. All rights reserved.
Erdelmeier I.,TETRAHEDRON |
Daunay S.,TETRAHEDRON |
Lebel R.,TETRAHEDRON |
Farescour L.,TETRAHEDRON |
Green Chemistry | Year: 2012
Biomass-derived cysteine was used as a sustainable sulfur source for the synthesis of rare sulfur-containing amino acids, such as l-ergothioneine (4), which might be a new vitamin, and various l- or d-2-thiohistidine compounds. Key in this simple, one-pot two-step procedure in water is a bromine-induced regioselective introduction of cysteine followed by a novel thermal cleavage reaction in the presence of thiols, a safer alternative to hazardous red phosphorus. Besides avoiding hazardous sulfur reagents, the new protecting-group-free approach reduces drastically the total number of steps, compared to described procedures. The main drawback, i.e. handling of liquid bromine as an activating and oxidizing reagent in water, was addressed by evaluating four alternative methods using in situ generation of bromine or HOBr, and first encouraging results are described. © 2012 The Royal Society of Chemistry.
Tetrahedron | Date: 2010-10-06
Methods for the synthesis of 2-thiohistidine or a derivative thereof of the formula (I), or of a physiologically acceptable salt, a tautomer, a stereoisomer or a mixture of stereoisomers in any proportions thereof, from a compound of the formula (II) or a physiologically acceptable salt, a tautomer, a stereoisomer or a mixture of stereoisomers in any proportions thereof, by cleavage reaction in the presence of a thiol at a temperature higher than or equal to 60 C. The invention also relates to compounds of the formula (II) and a method for the synthesis thereof.
Tetrahedron | Date: 2013-02-25
Chemicals used in industry, science and photography, as well as in agriculture, horticulture and forestry; chemical substances for preserving foodstuffs; chemical reagents other than for medical or veterinary use. Pharmaceutical and veterinary products; dietetic food and substances for medical or veterinary use; food for babies; food supplements for humans and animals; chemical preparations for medical or pharmaceutical use. Beers; mineral and carbonated waters; beverages based on fruit and fruit juices; fruit nectars. Wines.
Tetrahedron | Date: 2014-01-31
PubMed | Tetrahedron and CiToxLAB
Type: | Journal: Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association | Year: 2015
L-Ergothioneine is a naturally occurring histidine-derived betaine (CAS No: 497-30-3) synthesized by bacteria and fungi, and found ubiquitously in plants and animals. It is present in many human foodstuffs. We evaluated the potential reproductive toxicity of L-Ergothioneine in Sprague-Dawley rats. L-Ergothioneine was administered at concentrations of 0.1, 0.3 or 0.9% in diet to F0 males (for 10 weeks before pairing and 3 weeks during pairing) and F0 females (for 13 weeks before pairing, during pairing and gestation, and until day 5 of lactation). Systemic exposure increased with dose-level, but not dose proportionally, suggesting saturation of uptake mechanisms. No clinical signs of toxicity were observed and there were no effects of L-Ergothioneine treatment on mating and reproductive performance or parameters of fertility. All animals mated within a similar number of days and pregnancy rates were uniformly high in control and treated groups. There were no effects of treatment with L-Ergothioneine on the duration of gestation, pre- and post-implantation losses, number of pups delivered and viability index, or on litter parameters (litter size, clinical signs, body weight or sex ratio) and the repartition of found dead/cannibalized pups. In conclusion, L-Ergothioneine was well tolerated and without adverse effects on the reproductive parameters evaluated.