Browse
Submit Data
Databases
API
Help

Dataset Information

25 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Synthesis of polymer-bound 4-acetoxy-3-phenylbenzaldehyde derivatives: applications in solid-phase organic synthesis.

ABSTRACT: Aminomethyl polystyrene resin was reacted with 4-(5'-formyl-2'-hydroxyphenyl)benzoic acid and 4-(5'-formyl-2'-hydroxyphenyl)phenyl propionic acid, respectively, in the presence of 1-hydroxybenzotriazole and 1,3-diisopropylcarbodiimide to yield polymer-bound benzaldehydes. The phenolic group in resins was acetylated with acetic anhydride to afford two polymer-bound 4-acetoxybenzaldehydes. The reductive amination of polymer-bound linkers by amines and sodium triacetoxyborohydride, followed by sulfonylation with arylsulfonyl chloride derivatives in the presence of pyridine and the cleavage with TFA/DCM/H2O, produced pure sulfonamides.

SUBMITTER: Kumar A

PROVIDER: S-EPMC2532670 | biostudies-literature | 2006 Sep

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Synthesis of polymer-bound 4-acetoxy-3-phenylbenzaldehyde derivatives: applications in solid-phase organic synthesis.

Kumar Anil A Ye Guofeng G Ahmadibeni Yousef Y Parang Keykavous K

The Journal of organic chemistry 20060901 20

Aminomethyl polystyrene resin was reacted with 4-(5'-formyl-2'-hydroxyphenyl)benzoic acid and 4-(5'-formyl-2'-hydroxyphenyl)phenyl propionic acid, respectively, in the presence of 1-hydroxybenzotriazole and 1,3-diisopropylcarbodiimide to yield polymer-bound benzaldehydes. The phenolic group in resins was acetylated with acetic anhydride to afford two polymer-bound 4-acetoxybenzaldehydes. The reductive amination of polymer-bound linkers by amines and sodium triacetoxyborohydride, followed by sulf ...[more]

PMID: 16995713

Similar Datasets

Polymer-supported (2,6-dichloro- 4-alkoxyphenyl)(2,4-dichlorophenyl)methanol: a new linker for solid-phase organic synthesis.

Project description:An acid and base stable hydroxytetrachlorodiphenylmethyl (HTPM) linker is developed for polymer-supported organic synthesis. The linkers reported here are utilized for loading carboxylic acids, amines, alcohols, and phenols, and are stable to Brønsted and Lewis acids, Brønsted bases, and a wide variety of nucleophiles. However, the HTPM linkers can conveniently be cleaved by the solvolytic displacement reactions with 20% TFA. [structure: see text]

| S-EPMC2577291 | biostudies-literature

DNA display III. Solid-phase organic synthesis on unprotected DNA.

Project description:DNA-directed synthesis represents a powerful new tool for molecular discovery. Its ultimate utility, however, hinges upon the diversity of chemical reactions that can be executed in the presence of unprotected DNA. We present a solid-phase reaction format that makes possible the use of standard organic reaction conditions and common reagents to facilitate chemical transformations on unprotected DNA supports. We demonstrate the feasibility of this strategy by comprehensively adapting solid-phase 9-fluorenylmethyoxycarbonyl-based peptide synthesis to be DNA-compatible, and we describe a set of tools for the adaptation of other chemistries. Efficient peptide coupling to DNA was observed for all 33 amino acids tested, and polypeptides as long as 12 amino acids were synthesized on DNA supports. Beyond the direct implications for synthesis of peptide-DNA conjugates, the methods described offer a general strategy for organic synthesis on unprotected DNA. Their employment can facilitate the generation of chemically diverse DNA-encoded molecular populations amenable to in vitro evolution and genetic manipulation.

| S-EPMC434150 | biostudies-literature

Automated synthesis of prexasertib and derivatives enabled by continuous-flow solid-phase synthesis.

Project description:Recent advances in end-to-end continuous-flow synthesis are rapidly expanding the capabilities of automated customized syntheses of small-molecule pharmacophores, resulting in considerable industrial and societal impacts; however, many hurdles persist that limit the number of sequential steps that can be achieved in such systems, including solvent and reagent incompatibility between individual steps, cumulated by-product formation, risk of clogging and mismatch of timescales between steps in a processing chain. To address these limitations, herein we report a strategy that merges solid-phase synthesis and continuous-flow operation, enabling push-button automated multistep syntheses of active pharmaceutical ingredients. We demonstrate our platform with a six-step synthesis of prexasertib in 65% isolated yield after 32 h of continuous execution. As there are no interactions between individual synthetic steps in the sequence, the established chemical recipe file was directly adopted or slightly modified for the synthesis of twenty-three prexasertib derivatives, enabling both automated early and late-stage diversification.

| S-EPMC8054510 | biostudies-literature

Resin capsules: permeable containers for parallel/combinatorial solid-phase organic synthesis.

Project description:A resin capsule is a permeable container for resin beads designed for multiple/combinatorial solid-phase organic synthesis. Resin capsules consist of a high density polyethylene ring sealed with peek mesh on both sides. The cylindrical shape of resin capsules enabled space-saving packing into plastic columnlike reaction vessels commonly used for solid-phase organic synthesis. Resin capsules have been evaluated for their use in combinatorial synthesis, and a set of model compounds with excellent purity was prepared.

| S-EPMC2652863 | biostudies-literature

Yellow-Emitting Hydrophobic Carbon Dots via Solid-Phase Synthesis and Their Applications.

Project description:The preparation and application of hydrophobic carbon dots (HCDs) are now the hotspots in the field of nanomaterials. This paper reports the fast synthesis of long-wavelength-emitting HCDs (yellow-emitting, λem = 541 nm) through a solid-phase route, with l-cysteine hydrochloride anhydrous and citric acid as carbon sources and dicyclohexylcarbodiimide as a dehydrating agent, reacting at 180 °C for 40 min, with a quantum yield of 30%. The solid-phase route avoids the usage of organic reagents during the synthesis process and is thus environmentally friendly. The obtained HCDs can be simply separated into HCDs-L (less density) and HCDs-W (higher density) with differences in physical (polarity, density), optical, and chemical properties. The differences in HCDs-L, HCDs-W, and water-soluble CDs (WCDs) were compared through various characterization methods, and the synthesis and luminescence mechanisms of HCDs were investigated. Meanwhile, HCDs were employed in the fields of LED lamp production and solid fluorescent shaping material. The prepared HCDs were then modified into WCDs through the liposomal embedding method. The HCDs prepared by the new solid-phase route exhibit stable and highly efficient photoluminescence ability and will have a promising outlook in their applications in various fields.

| S-EPMC7482243 | biostudies-literature

Solid-phase synthesis of N-substituted glycine oligomers (alpha-peptoids) and derivatives.

Project description:Peptoids (N-substituted polyglycines and extended peptoids with variant backbone amino-acid monomer units) are oligomeric synthetic polymers that are becoming a valuable molecular tool in the biosciences. Of particular interest are their applications to the exploration of peptoid secondary structures and drug design. Major advantages of peptoids as research and pharmaceutical tools include the ease and economy of synthesis, highly variable backbone and side-chain chemistry possibilities. At the same time, peptoids have been demonstrated as highly active in biological systems while resistant to proteolytic decay. This review with 227 references considers the solid-phase synthetic aspects of peptoid preparation and utilization up to 2010 from the instigation, by R. N. Zuckermann et al., of peptoid chemistry in 1992.

| S-EPMC6257730 | biostudies-literature

The development of a dedicated polymer support for the solid-phase oligosaccharide synthesis.

Project description:Reported herein is the development of a novel polystyrene-based resin that we named PanzaGel. The resin was equipped with diethylene glycol-derived cross-linker with the dedicated application to polymer supported glycan synthesis in mind. After investigating its swelling properties and obtaining encouraging data for its chemical and thermal stability we accessed the amenability of PanzaGel to the HPLC-based platform for the automated synthesis. Comparable glycosylation results to those with traditional supports have been obtained in the synthesis of glycans up to pentasaccharide that was obtained in 30% overall yield. The automated synthesis set-up implemented a common analytical autosampler for delivering all reagents for all steps of the glycan synthesis and cleavage.

| S-EPMC7658588 | biostudies-literature

Divergent behavior of glycosylated threonine and serine derivatives in solid phase peptide synthesis.

Project description:Solid phase peptide coupling of glycosylated threonine derivatives was systematically evaluated. In contrast to glycosylated serine derivatives which are highly prone to epimerization, glycosylated threonine derivatives produce only negligible amounts of epimerization. Under forcing conditions, glycosylated threonine analogs undergo ?-elimination, rather than epimerization. Mechanistic studies and molecular modeling were used to understand the origin of the differences in reactivity.

| S-EPMC3417326 | biostudies-literature

Solid-Phase Synthesis of Molecularly Imprinted Polymer Nanoparticles with a Reusable Template - "Plastic Antibodies".

Project description:Molecularly Imprinted Polymers (MIPs) are generic alternatives to antibodies in sensors, diagnostics and separations. To displace biomolecules without radical changes in infrastructure in device manufacture, MIPs should share their characteristics (solubility, size, specificity and affinity, localized binding domain) whilst maintaining the advantages of MIPs (low-cost, short development time and high stability) hence the interest in MIP nanoparticles. Herein we report a reusable solid-phase template approach (fully compatible with automation) for the synthesis of MIP nanoparticles and their precise manufacture using a prototype automated UV photochemical reactor. Batches of nanoparticles (30-400 nm) with narrow size distributions imprinted with: melamine (d = 60 nm, Kd = 6.3 × 10-8 m), vancomycin (d = 250 nm, Kd = 3.4 × 10-9 m), a peptide (d = 350 nm, Kd = 4.8 × 10-8 m) and proteins have been produced. Our instrument uses a column packed with glass beads, bearing the template. Process parameters are under computer control, requiring minimal manual intervention. For the first time we demonstrate the reliable re-use of molecular templates in the synthesis of MIPs (? 30 batches of nanoMIPs without loss of performance). NanoMIPs are produced template-free and the solid-phase acts both as template and affinity separation medium.

| S-EPMC4746745 | biostudies-literature

Solid-Phase Synthesis of Diverse Macrocycles by Regiospecific 2-Pyridone Formation: Scope and Applications.

Project description:This study introduces a novel solid-phase macrocyclization method generating 2-pyridone rings. This method relies on the intramolecular condensation between secondary and tertiary dimethoxy-propionic amide units. This selective reaction leads to the formation of a single well-defined regioisomer. The method demonstrates remarkable efficiency in producing diverse peptidic and nonpeptidic bioactive targets, paving the way for the development of innovative macrocycle libraries featuring the 2-pyridone unit.

| S-EPMC11350735 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

Tweets

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