Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Direct formation of amide/peptide bonds from carboxylic acids: no traditional coupling reagents, 1-pot, and green.

ABSTRACT: Technology for generating especially important amide and peptide bonds from carboxylic acids and amines that avoids traditional coupling reagents is described. The 1-pot processes developed rely on thioester formation, neat, using a simple dithiocarbamate, and are safe and green, and rely on Nature-inspired thioesters that are then converted to the targeted functionality.

SUBMITTER: Freiberg KM

PROVIDER: S-EPMC10055766 | biostudies-literature | 2023 Mar

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Direct formation of amide/peptide bonds from carboxylic acids: no traditional coupling reagents, 1-pot, and green.

Freiberg Kaitlyn M KM Kavthe Rahul D RD Thomas Rohan M RM Fialho David M DM Dee Paris P Scurria Matthew M Lipshutz Bruce H BH

Chemical science 20230228 13

Technology for generating especially important amide and peptide bonds from carboxylic acids and amines that avoids traditional coupling reagents is described. The 1-pot processes developed rely on thioester formation, neat, using a simple dithiocarbamate, and are safe and green, and rely on Nature-inspired thioesters that are then converted to the targeted functionality. ...[more]

PMID: 37006678

Similar Datasets

Carboxylic acid isomer-directed synthesis of CdS nanocluster isomers† † Electronic supplementary information (ESI) available. See DOI: https://doi.org/10.1039/d4sc01569j

Project description: Not available

| S-EPMC11234825 | biostudies-literature

The power of microdroplet photochemistry† † Electronic supplementary information (ESI) available. See DOI: https://doi.org/10.1039/d4sc00056k

Project description: Not available

| S-EPMC10915808 | biostudies-literature

Total synthesis of bi-magnolignan† † Electronic supplementary information (ESI) available. See DOI: https://doi.org/10.1039/d3ra01121f

Project description:Bi-magnolignan, isolated from the leaves of Magnolia officinalis, has shown excellent physiological activity against tumor cells. An efficient strategy for the first total synthesis of bi-magnolignan is reported. The bi-dibenzofuran skeleton was constructed via functional group interconversions of commercially available materials 1,2,4-trimethoxybenzene and 4-allylanisole. Then, the dibenzofuran skeleton was afforded by subsequent Suzuki coupling and intramolecular dehydration. The total synthesis of natural product was accomplished through FeCl3 catalyzed oxidative coupling. The first total synthesis of bi-magnolignan in eight steps from commercially available starting materials has been developed.

| S-EPMC10018648 | biostudies-literature

Boric acid catalysed hydrolysis of peroxyacids† † Electronic supplementary information (ESI) available. See DOI: https://doi.org/10.1039/d3ra01046e

Project description:This study shows for the first time that boric acid catalyses the hydrolysis of peroxyacids, resulting in an approximately 12-fold increase in hydrolysis rate for both peracetic acid (PAA) and 3-chloroperbenzoic acid (MCPBA) when 0.1 M boric acid is present. The maximum rate of hydrolysis occurs at pH 9 and pH 8.4 for PAA and MCPBA respectively. In contrast, carbonate buffer does not enhance the rate of PAA hydrolysis. The reaction was followed by measuring the initial rate of hydrogen peroxide formation using a specific Ti(iv) complexation method. The study of the hydrolysis reaction requires the presence of 2 × 10−5 M each of ethylenediaminetetraacetic acid (EDTA) and ethylenediamine tetramethylene phosphonic acid (EDTMP) in all solutions in order to chelate metal ions across the full pH range (3 to 13) that would otherwise contribute to peroxyacid decomposition. Catalysis of peroxyacid hydrolysis is most likely effected by the triganol boric acid acting as a Lewis acid catalyst, associating with the peroxide leaving group in the transition state to reduce the leaving group basicity. The products of the reaction are the well characterised monoperoxoborate species and the parent carboxylic acid. Analysis of the pH and borate dependence data reveals that in addition to a catalytic pathway involving a single boric acid molecule, there is a significant pathway involving either (a) two boric acid molecules or (b) the polyborate species, B3O3(OH)4−. Knowledge about catalytic mechanisms for the loss of peroxyacids through hydrolysis is important because they are widely used in reagents in a range of oxidation, bleaching and disinfection applications. Boric acid catalyses the hydrolysis of peroxyacids, with possible pathways involving one and two molecules of boric acid as well as polyborate species.

| S-EPMC10103745 | biostudies-literature

AI facilitated fluoro-electrochemical phytoplankton classification† † Electronic supplementary information (ESI) available. See DOI: https://doi.org/10.1039/d3sc01741a

Project description:Marine phytoplankton is extremely diverse. Counting and characterising phytoplankton is essential for understanding climate change and ocean health not least since phytoplankton extensively biomineralize carbon dioxide whilst generating 50% of the planet's oxygen. We report the use of fluoro-electrochemical microscopy to distinguish different taxonomies of phytoplankton by the quenching of their chlorophyll-a fluorescence using chemical species oxidatively electrogenerated in situ in seawater. The rate of chlorophyll-a quenching of each cell is characteristic of the species-specific structural composition and cellular content. But with increasing diversity and extent of phytoplankton species under study, human interpretation and distinction of the resulting fluorescence transients becomes increasingly and prohibitively difficult. Thus, we further report a neural network to analyse these fluorescence transients, with an accuracy >95% classifying 29 phytoplankton strains to their taxonomic orders. This method transcends the state-of-the-art. The success of the fluoro-electrochemical microscopy combined with AI provides a novel, flexible and highly granular solution to phytoplankton classification and is adaptable for autonomous ocean monitoring. Schematic of fluoro-electrochemical microscopy. (a) Cartoon E. huxleyi is green under normal light, but (b) emits red fluorescence under UV. (c) Placed near an oxidizing electrode, its fluorescence fades and ultimately (d) “switches off”.

| S-EPMC10246652 | biostudies-literature

Electrically conductive [Fe4S4]-based organometallic polymers† † Electronic supplementary information (ESI) available. See DOI: https://doi.org/10.1039/d3sc02195e

Project description: Not available

| S-EPMC10599474 | biostudies-literature

Straightforward synthesis of N-arylindoles via one-pot Fischer indolisation–indole N-arylation† † Electronic supplementary information (ESI) available. See DOI: https://doi.org/10.1039/d3ra02658b

Project description:A microwave-promoted, one-pot, three-component synthesis of N-arylindoles has been developed, utilising sequential Fischer indolisation then copper(i)-catalysed indole N-arylation. Novel arylation conditions were identified that use a simple and cheap catalyst/base system (Cu2O/K3PO4) in an environmentally benign solvent (ethanol), with no requirement for ligands, additives or exclusion of air or water, and microwave irradiation enabled significant acceleration of this commonly sluggish process. These conditions were designed to dovetail with Fischer indolisation, and the resulting one-pot, two-step sequence is rapid (total reaction time = 40 minutes), operationally straightforward, generally high yielding and it draws upon readily available hydrazine, ketone/aldehyde and aryl iodide building blocks. This process shows broad substrate tolerance and we have demonstrated its utility in the synthesis of 18 N-arylindoles bearing varied and useful functionality. One-pot, microwave-promoted Fischer indolisation–indole N-arylation enables straightforward, rapid synthesis of structurally-diverse N-arylindoles from widely-available precursors, using a simple, air-stable catalyst in a common, sustainable solvent.

| S-EPMC10214496 | biostudies-literature

Concise two-step chemical synthesis of molnupiravir† † Electronic supplementary information (ESI) available. See DOI: https://doi.org/10.1039/d2ra05064a

Project description:A concise synthesis of molnupiravir in a one-pot two-step approach starting from uridine is described. Formally, herein, two sets of one-pot two-reaction steps introducing simplicity for purifications and using chemically available reagents are presented. In this context, molnupiravir was obtained in up to 68% overall yield and multigram-scale. In addition, HPLC analysis showed the molnupiravir purity above 99%. Fast, effective and chromatography column-free chemical synthesis of molnupiravir.

| S-EPMC9585438 | biostudies-literature

Deaminative coupling of benzylamines and arylboronic acids† † Electronic supplementary information (ESI) available. See DOI: https://doi.org/10.1039/d2sc06055h

Project description:A metal-free deaminative coupling of non-prefunctionalised benzylamines and arylboronic acids is reported. In this operationally simple reaction, a primary amine in benzylamine is converted into a good leaving group in situ using inexpensive and commercially available isoamyl nitrite as a nitrosating reagent. Lewis-acidic arylboronic acids are shown to replace mineral acids such as HCl or HBF4 that are conventionally used in the preparation of aryl diazonium salts. This unlocked the formation of the corresponding diarylmethanes by forging a new C–C bond in good yields. A metal-free deaminative coupling of non-prefunctionalised benzylamines and arylboronic acids is reported.

| S-EPMC9930926 | biostudies-literature

Pathway-dependent supramolecular polymerization by planarity breaking† † Electronic supplementary information (ESI) available. See DOI: https://doi.org/10.1039/d4sc02499k

Project description: Not available

| S-EPMC11253169 | biostudies-literature