Browse
Submit Data
Databases
API
Help

Dataset Information

6 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Synthesis of a Stable Primary-Alkyl-Substituted Selenenyl Iodide and Its Hydrolytic Conversion to the Corresponding Selenenic Acid.

ABSTRACT: A primary-alkyl-substituted selenenyl iodide was successfully synthesized through oxidative iodination of a selenol with N-iodosuccinimide by taking advantage of a cavity-shaped steric protection group. The selenenyl iodide exhibited high thermal stability and remained unchanged upon heating at 100 °C for 3 h in [D?]toluene. The selenenyl iodide was reduced to the corresponding selenol by treatment with dithiothreitol. Hydrolysis of the selenenyl iodide under alkaline conditions afforded the corresponding selenenic acid almost quantitatively, corroborating the chemical validity of the recent proposal that hydrolysis of a selenenyl iodide to a selenenic acid is potentially involved in the catalytic mechanism of an iodothyronine deiodinase.

SUBMITTER: Sase S

PROVIDER: S-EPMC6331843 | biostudies-other | 2015 Dec

REPOSITORIES: biostudies-other

ACCESS DATA

Json Xml

Publications

Synthesis of a Stable Primary-Alkyl-Substituted Selenenyl Iodide and Its Hydrolytic Conversion to the Corresponding Selenenic Acid.

Sase Shohei S Kakimoto Ryo R Kimura Ryutaro R Goto Kei K

Molecules (Basel, Switzerland) 20151202 12

A primary-alkyl-substituted selenenyl iodide was successfully synthesized through oxidative iodination of a selenol with N-iodosuccinimide by taking advantage of a cavity-shaped steric protection group. The selenenyl iodide exhibited high thermal stability and remained unchanged upon heating at 100 °C for 3 h in [D₈]toluene. The selenenyl iodide was reduced to the corresponding selenol by treatment with dithiothreitol. Hydrolysis of the selenenyl iodide under alkaline conditions afforded the cor ...[more]

PMID: 26633336

Similar Datasets

Synthesis and Hydrolytic Degradation of Substituted Poly(DL-Lactic Acid)s.

Project description:Non-substituted racemic poly(DL-lactic acid) (PLA) and substituted racemic poly(DL-lactic acid)s or poly(DL-2-hydroxyalkanoic acid)s with different side-chain lengths, i.e., poly(DL-2-hydroxybutanoic acid) (PBA), poly(DL-2-hydroxyhexanoic acid) (PHA), and poly(DL-2-hydroxydecanoic acid) (PDA) were synthesized by acid-catalyzed polycondensation of DL-lactic acid (LA), DL-2-hydroxybutanoic acid (BA), DL-2-hydroxyhexanoic acid (HA), and DL-2-hydroxydecanoic acid (DA), respectively. The hydrolytic degradation behavior was investigated in phosphate-buffered solution at 80 and 37 °C by gravimetry and gel permeation chromatography. It was found that the reactivity of monomers during polycondensation as monitored by the degree of polymerization (DP) decreased in the following order: LA > DA > BA > HA. The hydrolytic degradation rate traced by DP and weight loss at 80 °C decreased in the following order: PLA > PDA > PHA > PBA and that monitored by DP at 37 °C decreased in the following order: PLA > PDA > PBA > PHA. LA and PLA had the highest reactivity during polymerization and hydrolytic degradation rate, respectively, and were followed by DA and PDA. BA, HA, PBA, and PHA had the lowest reactivity during polymerization and hydrolytic degradation rate. The findings of the present study strongly suggest that inter-chain interactions play a major role in the reactivity of non-substituted and substituted LA monomers and degradation rate of the non-substituted and substituted PLA, along with steric hindrance of the side chains as can be expected.

| S-EPMC5448671 | biostudies-other

Lactic Acid Conversion to Acrylic Acid Over Fluoride-Substituted Hydroxyapatites.

Project description:One of the most interesting intermediates for the chemical industry is acrylic acid, which can be derived from lactic acid by catalytic dehydration in the gas phase. The realization of this reaction is complex due to a strong thermal activation leading to the formation of undesired by-products (acetaldehyde, propanoic acid…) as well as polymerization. We studied this reaction over hydroxyapatites modified by substitution of the hydroxyl groups by fluoride. This notably enabled increasing the selectivity to acrylic acid while reducing the formation of the undesired acetaldehyde. Introduction of fluoride induced a modification of the phosphate ( PO43- ) groups. In the presence of water, fluoride prevented the formation of hydrogenophosphate species ( HPO42- ), which are well-known acid sites responsible for the formation of acetaldehyde by decarboxylation/decarbonylation. Further, we evidenced an important impact of fluoride substitution on crystallinity, specific surface area and on the surface Ca/P ratio. This latter is known to be a key parameter to control the acidity and the basicity of the hydroxyapatites. Using FT-IR spectroscopy with propyne as a probe molecule, we could show that lactic acid was concertedly adsorbed on basic and acid sites, which might be at the origin of the observed superior performances.

| S-EPMC7237761 | biostudies-literature

Synthesis of 2-substituted tryptophans via a C3- to C2-alkyl migration.

Project description:The reaction of 3-substituted indoles with dehydroalanine (Dha) derivatives under Lewis acid-mediated conditions has been investigated. The formation of 2-substituted tryptophans is proposed to occur through a selective alkylative dearomatization-cyclization followed by C3- to C2-alkyl migration and rearomatization.

| S-EPMC4168769 | biostudies-literature

Poly(4-ketovalerolactone) from Levulinic acid: Synthesis and Hydrolytic Degradation.

Project description:We report here the synthesis of poly(4-ketovalerolactone) (PKVL) via ring-opening transesterification polymerization (ROTEP) of the monomer 4-ketovalerolactone (KVL, two steps from levulinic acid). The polymerization of KVL proceeds to high equilibrium monomer conversion (up to 96% in the melt) to give the semicrystalline polyketoester PKVL with low dispersity. PKVL displays glass transition temperatures of 7 °C and two melting temperatures at 132 and 148 °C. This polyester can be chemically recycled through hydrolytic degradation. Under aqueous neutral or acidic conditions, the dominating pathway for polyester hydrolysis is through backbiting from the chain end. Under basic conditions, mid-chain cleavage, accelerated by the ketone carbonyl group in the backbone, promotes the hydrolysis of nearby backbone ester bonds. The final hydrolysis product is 5-hydroxylevulinic acid, the ring opened hydrolysis product of KVL. PKVL was also observed to degrade under the action of a Brønsted acid to a bis-spirocyclic dilactone natural product altaicadispirolactone, which is a dimer of KVL. This constitutes a rare example of a one-step synthesis of a secondary metabolite of non-trivial structure in which a polymer was the starting material and the sole source of matter. Analogous ROTEP of the isomeric 4-membered lactone 4-acetyl-β-propiolactone (APL) was also explored, although this chemistry was not as well-behaved as the KVL to PKVL polymerization.

| S-EPMC7987374 | biostudies-literature

CuH-Catalyzed Regioselective Intramolecular Hydroamination for the Synthesis of Alkyl-Substituted Chiral Aziridines.

Project description:This report details a general and enantioselective means for the synthesis of alkyl-substituted aziridines. This protocol offers a direct route for the synthesis of alkyl-substituted chiral aziridines from achiral starting materials. Readily accessed allylic hydroxylamine esters undergo copper hydride-catalyzed intramolecular hydroamination with a high degree of regio- and enantiocontrol to afford the aziridine products in good to excellent yields in highly enantioenriched form. The utility of the products derived from this method is further demonstrated through derivatization of the chiral aziridine products to obtain a diverse array of functionalized enantioenriched amines.

| S-EPMC5656387 | biostudies-literature

Chiral Bronsted base-promoted nitroalkane alkylation: enantioselective synthesis of sec-alkyl-3-substituted indoles.

Project description:A Brønsted base-catalyzed reaction of nitroalkanes with alkyl electrophiles provides indole heterocycles substituted at C3 bearing a sec-alkyl group with good enantioselectivity (up to 90% ee). Denitration by hydrogenolysis provides a product with equally high ee. An indolenine intermediate is implicated in the addition step, and surprisingly, water cosolvent was found to have a beneficial effect in this step, leading to a one-pot protocol for elimination/enantioselective addition using PBAM, a bis(amidine) chiral nonracemic base.

| S-EPMC3005818 | biostudies-literature

Synthesis of cholesteryl-?-D-lactoside via generation and trapping of a stable ?-lactosyl iodide.

Project description:The generation of ?-lactosyl iodide was carried out under non-in situ-anomerization, metal free conditions by reacting commercially available ?-per-O-acetylated lactose with trimethylsilyl iodide (TMSI). The ?-iodide was surprisingly stable as evidenced by NMR spectroscopy. Introduction of octanol or cholesterol under microwave conditions gave high yields of ?-linked glycoconjugates. Careful analysis of the reaction products and mechanistic considerations suggest an acid catalyzed rearrangement that provides ?-linked glycosylation products with a free C2-hydroxyl. Accessibility to these compounds may further advance glycolipidomic profiling of immune modulating bacterial derived-glycans.

| S-EPMC4629507 | biostudies-literature

Alkyl-Substituted ?-Lactones Derived from Dihydrojasmone and Their Stereoselective Fungi-Mediated Conversion: Production of New Antifeedant Agents.

Project description:A chemoenzymatic method was applied to obtain optically pure alkyl-substituted ?-lactones. First, chemical Baeyer-Villiger oxidation of dihydrojasmone (1) was carried out, affording two new alkyl-substituted ?-lactones: 3,4-dihydro-5-methyl-6-pentyl-2H-pyran-2-one (2) and 5-methyl-6-pentyl-1,13-dioxabicyclo[4.1.0]heptan-2-one (3). In the next step, fungal strains were investigated as biocatalysts to enantioselective conversion of ?-lactones (2) and (3). The fungal cultures: Fusarium culmorum AM10, Fusarium equiseti AM15 and Beauveria bassiana AM278 catalyzed the stereoselective hydration of the double bond of lactone (2) (ee = 20%-99%) while Didymosphaeria igniaria KCh6670 proved to be the best biocatalyst for the reduction of carbonyl group in the epoxylactone (3) (ee = 99%). In both cases, chiral oxyderivatives were obtained in low to high yields (7%-91%). The synthetic lactones (2), (3) and its derivatives (4), (5) were tested for their antifeedant activity towards larvae and adults of lesser mealworm (Alphitobius diaperinus Panzer) and peach potato aphid (Myzus persicae [Sulzer]) and some of them were active towards studied insects.

| S-EPMC6273879 | biostudies-other

Transistor application of alkyl-substituted picene.

Project description:Field-effect transistors (FETs) were fabricated with a thin film of 3,10-ditetradecylpicene, picene-(C14H29)2, formed using either a thermal deposition or a deposition from solution (solution process). All FETs showed p-channel normally-off characteristics. The field-effect mobility, ?, in a picene-(C14H29)2 thin-film FET with PbZr0.52Ti0.48O3 (PZT) gate dielectric reached ~21?cm2 V(-1) s(-1), which is the highest ? value recorded for organic thin-film FETs; the average ? value (<?>) evaluated from twelve FET devices was 14(4)?cm2 V(-1) s(-1). The <?> values for picene-(C14H29)2 thin-film FETs with other gate dielectrics such as SiO2, Ta2O5, ZrO2 and HfO2 were greater than 5?cm2 V(-1) s(-1), and the lowest absolute threshold voltage, |Vth|, (5.2?V) was recorded with a PZT gate dielectric; the average |Vth| for PZT gate dielectric is 7(1)?V. The solution-processed picene-(C14H29)2 FET was also fabricated with an SiO2 gate dielectric, yielding ?=3.4×10(-2)?cm2 V(-1) s(-1). These results verify the effectiveness of picene-(C14H29)2 for electronics applications.

| S-EPMC4031476 | biostudies-other

Synthesis and antimicrobial activity of some novel 5-alkyl-6-substituted uracils and related derivatives.

Project description:6-chloro-5-ethyl-, n-propyl- and isopropyluracils 5a-c were efficiently prepared from the corresponding 5-alkybarbituric acids 3a-c via treatment with phosphorus oxychloride and N,N-dimethylaniline to yield the corresponding 5-alkyl-2,4,6-trichloro-pyrimidines 4a-c, which were selectively hydrolyzed by heating in 10% aqueous sodium hydroxide for 30 minutes. The reaction of compounds 5a-c with 1-substituted piperazines yielded the corresponding 5-alkyl-6-(4-substituted-1-piperazinyl)uracils 6a-j. The target 8-alkyltetrazolo[1,5-f]pyrimidine-5,7(3H,6H)-diones 7a-c were prepared via the reaction of 5a-c with sodium azide. Compounds 6a-j and 7a-c were tested for in vitro activities against a panel of Gram-positive and Gram-negative bacteria and the yeast-like pathogenic fungus Candida albicans. Compound 6h displayed potent broad-spectrum antibacterial activity, while compound 6b showed moderate activity against the Gram-positive bacteria. All the tested compounds were practically inactive against Candida albicans.

| S-EPMC6264406 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

OmicsDI Databases

PRIDE
PeptideAtlas
MassIVE
JPOST Repository
Physiome Model Repository

EGA
EVA
ENA
LINCS
PAXDB
Cell Collective

MetaboLights
Metabolomics Workbench
MetabolomeExpress
GNPS
BioModels
FAIRDOMHub

ArrayExpress
dbGaP
ExpressionAtlas
GEO
NODE

Information

Databases
Help
API
Contact us
Code on GitHub
Terms of use
Submit Data