Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Automated fluorous-assisted solution-phase synthesis of ?-1,2-, 1,3-, and 1,6-mannan oligomers.

ABSTRACT: Automated solution-phase syntheses of ?-1,2-, 1,3-, and 1,6-mannan oligomers have been accomplished by applying a ?-directing C-5 carboxylate strategy. Fluorous-tag-assisted purification after each reaction cycle allowed the synthesis of short ?-mannan oligomers with limited loading of glycosyl donor-as low as 3.0 equivalents for each glycosylation cycle. This study showed the capability of the automated solution-phase synthesis protocol for synthesizing various challenging glycosides, including use of a C-5 ester as a protecting group that could be converted under reductive conditions to a hydroxymethyl group for chain extension.

SUBMITTER: Tang SL

PROVIDER: S-EPMC4893899 | biostudies-literature | 2016 Jul

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Automated fluorous-assisted solution-phase synthesis of β-1,2-, 1,3-, and 1,6-mannan oligomers.

Tang Shu-Lun SL Pohl Nicola L B NLB

Carbohydrate research 20160406

Automated solution-phase syntheses of β-1,2-, 1,3-, and 1,6-mannan oligomers have been accomplished by applying a β-directing C-5 carboxylate strategy. Fluorous-tag-assisted purification after each reaction cycle allowed the synthesis of short β-mannan oligomers with limited loading of glycosyl donor-as low as 3.0 equivalents for each glycosylation cycle. This study showed the capability of the automated solution-phase synthesis protocol for synthesizing various challenging glycosides, including ...[more]

PMID: 27155895

Similar Datasets

Automated Solution-Phase Synthesis of β-1,4-Mannuronate and β-1,4-Mannan.

Project description:The first automated solution-phase synthesis of β-1,4-mannuronate and β-1,4-mannan oligomers has been accomplished by using a β-directing C-5 carboxylate strategy. By utilizing fluorous-tag assisting purification after repeated reaction cycles, β-1,4-mannuronate was synthesized up to a hexasaccharide with limited loading of a glycosyl donor (up to 3.5 equiv) for each glycosylation cycle due to the homogeneous solution-phase reaction condition. After a global reduction of the uronates, the β-1,4-mannan hexasaccharide was obtained, thereby demonstrating a new approach to β-mannan synthesis.

| S-EPMC4460921 | biostudies-literature

Regio- and sequence-controlled conjugated topological oligomers and polymers via boronate-tag assisted solution-phase strategy.

Project description:The regulation of polymer topology and the precise control over the monomer sequence is crucial and challenging in polymer science. Herein, we report an efficient solution-phase synthetic strategy to prepare regio- and sequence-controlled conjugated polymers with topological variations via the usage of methyliminodiacetic acid (MIDA) boronates. Based on the solubility of MIDA boronates and their unusual binary affinity for silica gel, the synthesized regio- and sequence-defined conjugated oligomers can be rapidly purified via precipitation or automatic liquid chromatography. These synthesized discrete oligomers can be used for iterative exponential and sequential growth to obtain linear and dendrimer-like star polymers. Moreover, different topological sequence-controlled conjugated polymers are conveniently prepared from these discrete oligomers via condensation polymerization. By investigating the structure-property relationship of these polymers, we find that the optical properties are strongly influenced by the regiochemistry, which may give inspiration to the design of optoelectronic polymeric materials.

| S-EPMC8494804 | biostudies-literature

Fluorous-Assisted One-Pot Oligosaccharide Synthesis.

Project description:A new method for oligosaccharide assembly that combines the advantages of one-pot synthesis and fluorous separation is described. After one-pot glycosylations are completed, a fluorous tag is introduced into the reaction mixture to selectively "catch" the desired oligosaccharide, which is rapidly separated from non-fluorous impurities by fluorous solid-phase extraction (F-SPE). Subsequent "release" of the fluo rous tag and F-SPE achieved the purification of the desired oligosaccharide without the use of time- and solvent-consuming silica gel chromatography. Linear and branched oligosaccharides have been synthesized with this approach in just a few hours (for the overall oligosaccharide assembly and purification process).

| S-EPMC3324286 | biostudies-literature

Peptidines: glycine-amidine-based oligomers for solution- and solid-phase synthesis.

Project description:Efforts to emulate biological oligomers have given rise to a host of useful technologies, ranging from solid-phase peptide and nucleic acid synthesis to various peptidomimetic platforms. Herein we introduce a novel class of peptide-like oligomers called "peptidines" wherein each carbonyl O-atom within poly-N-alkyl glycine oligomers is replaced with a functionalized N-atom. Compared to peptoids or peptides, the presence of this amidine N-substituent in peptidines effectively doubles the number of diversification sites per monomeric unit, and can decrease their overall conformational flexibility. We have developed iterative solution- and solid-phase protocols for the straightforward assembly of peptidines containing diverse backbone and amidine substituents, derived from readily available primary and secondary amines. We have also performed crystallographic and computational studies, which demonstrate a strong preference for the trans (E) amidine geometry. Given their straightforward synthetic preparation and high functional group density, peptidines have the potential to serve as useful tools for library generation, peptide mimicry, and the identification of biologically active small molecules.

| S-EPMC6006957 | biostudies-literature

Immune response to intra-ocular injection of particulate β-(1,3)(1,6) glucan

Project description:Description of cellular and molecular landscape of vitreal immune cells following optic nerve crush injury plus intra-ocular injection of particulate β-glucan after 3days, in WT and Itgam-/- mice

2024-07-03 | GSE244627 | GEO

Solution-phase parallel synthesis of a diverse library of 1,2-dihydroisoquinolines.

Project description:Synthesis of a 105 membered library of 1,2-dihydroisoquinolines is described. The 1,2-dihydroisoquinoline compounds have been prepared in good yields using a Lewis acid and organocatalyst-cocatalyzed multicomponent reaction of 2-(1-alkynyl)benzaldehydes, amines, and ketones. Various indoles have also been employed as pronucleophiles, furnishing 1-(3-indolyl)-1,2-dihydroisoquinolines. The halogen functionality present in some of the synthesized compounds allows for further diversification by palladium-catalyzed Suzuki?Miyaura and Sonogashira cross-couplings to give more diversified 1,2-dihydroisoquinoline derivatives.

| S-EPMC3118513 | biostudies-literature

Fluorous-assisted chemoenzymatic synthesis of heparan sulfate oligosaccharides.

Project description:The chemoenzymatic synthesis of heparan sulfate tetrasaccharide (1) and hexasaccharide (2) with a fluorous tag attached at the reducing end is reported. The fluorous tert-butyl dicarbonate ((F)Boc) tag did not interfere with enzymatic recognition for both elongation and specific sulfation, and flash purification was performed by standard fluorous solid-phase extraction (FSPE). Based on an (F)Boc attached disaccharide as acceptor, a series of partial N-sulfated, 6-O-sulfated heparan sulfate oligosaccharides were successfully synthesized employing fluorous techniques.

| S-EPMC3998769 | biostudies-literature

Fluorous-Phase Approach to α-Hydroxytropolone Synthesis.

Project description:α-Hydroxytropolones (αHTs) are troponoids that demonstrate inhibition against an array of therapeutically significant targets, making them potential drug leads for several human diseases. We have utilized a recently discovered one-pot three-component oxidopyrylium cycloaddition in a solid-supported synthesis of αHTs. Though the procedure is time efficient and generates assay-ready molecules, the system suffers from low yields and an inability to perform reaction modifications on resin-bound intermediates. In order to combat these issues with the solid-phase platform, we incorporated fluorous tags into our synthetic route. Through the implementation of fluorous phase chemistry, we demonstrate a substantial increase in the overall yield of αHTs, as well as an ability to execute metal-catalyzed cross coupling and amide coupling on fluorous tagged intermediates. We also show that tagged molecules can be separated from nonfluorous impurities, and vice versa, by utilizing fluorous liquid-liquid and solid-phase extractions. Hence, these proof-of-principle investigations describe the viability of a fluorous phase approach to αHT synthesis and its potential to serve as a combinatorial technique to produce structurally diverse substrates.

| S-EPMC5859309 | biostudies-literature

1,3-Diphenyl-3,4-dihydro-benzo[b][1,6]naphthyridine.

Project description:The title compound, C(24)H(18)N(2), is the first structural example containing the 3,4-dihydro-benzo[b][1,6]naphthyridine fragment. It was synthesized from 2,4,6,8-tetra-phenyl-3,7-diaza-bicyclo-[3.3.1]nonan-9-one and was crystallized from a methanol-ethanol solution over two years as a racemate. The C=N double bond [1.2868?(15)?Å] is bent significantly out of the plane of the aromatic bicyclic ring system [N-C-C-C = -157.63?(12)°] and out of the plane of the phenyl ring bonded at the 1-position [N-C-C-C = 41.15?(16)°].

| S-EPMC2979077 | biostudies-literature

4,9-Dioxa-1,3(1,2)-dibenzena-2(4,5)-1,3-oxazolidinacyclononaphane.

Project description:The oxazole ring in the title compound, C(20)H(23)NO(3), adopts an envelope conformation while the 12-membered ring is in a chair conformation. The dihedral angle between the benzene rings is 37.8 (1)°. The crystal structure displays inter-molecular C-H⋯O hydrogen bonding.

| S-EPMC3051461 | 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