Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Solid-phase synthesis of peptidyl thioacids employing a 9-fluorenylmethyl thioester-based linker in conjunction with Boc chemistry.

ABSTRACT: A method for the synthesis of peptidyl thioacids is described on the basis of the use of the N-[9-(thiomethyl)-9H-fluoren-2-yl]succinamic acid and cross-linked aminomethyl polystyrene resin. The method employs standard Boc chemistry SPPS techniques in conjunction with 9-fluorenylmethyloxycarbonyl protection of side-chain alcohols and amines and 9-fluorenylmethyl protection of side-chain acids and thiols. Cleavage from the resin is accomplished with piperidine, which also serves to remove the side-chain protection and avoids the HF conditions usually associated with the resin cleavage stage of Boc chemistry SPPS. The so-obtained thioacids are converted to simple thioesters in high yield by standard alkylation according to well-established methods.

SUBMITTER: Crich D

PROVIDER: S-EPMC2778002 | biostudies-literature | 2009 Oct

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Solid-phase synthesis of peptidyl thioacids employing a 9-fluorenylmethyl thioester-based linker in conjunction with Boc chemistry.

Crich David D Sana Kasinath K

The Journal of organic chemistry 20091001 19

A method for the synthesis of peptidyl thioacids is described on the basis of the use of the N-[9-(thiomethyl)-9H-fluoren-2-yl]succinamic acid and cross-linked aminomethyl polystyrene resin. The method employs standard Boc chemistry SPPS techniques in conjunction with 9-fluorenylmethyloxycarbonyl protection of side-chain alcohols and amines and 9-fluorenylmethyl protection of side-chain acids and thiols. Cleavage from the resin is accomplished with piperidine, which also serves to remove the sid ...[more]

PMID: 19725529

Similar Datasets

Direct Fmoc-chemistry-based solid-phase synthesis of peptidyl thioesters.

Project description:Attachment of a growing peptide chain to a glycylaminomethyl resin via a thioglycinamide bond is compatible with Fmoc-chemistry solid-phase peptide synthesis. Subsequent S-alkylation of the thioamide gives a thioimide that, on treatment with aqueous trifluoroacetic acid, releases the peptide from the resin in the form of a C-terminal thioester.

| S-EPMC3184774 | biostudies-literature

A Tripeptide Approach to the Solid-Phase Synthesis of Peptide Thioacids and N-Glycopeptides.

Project description:A general and robust method for the incorporation of aspartates with a thioacid side chain into peptides has been developed. Pseudoproline tripeptides served as building blocks for the efficient fluorenylmethyloxycarbonyl (Fmoc) solid-phase synthesis of thioacid-containing peptides. These peptides were readily converted to complex N-glycopeptides by using a fast and chemoselective one-pot deprotection/ligation procedure. Furthermore, a novel side reaction that can lead to site-selective peptide cleavage using thioacids (CUT) was discovered and studied in detail.

| S-EPMC6916195 | biostudies-literature

Solid phase chemistry to covalently and reversibly capture thiolated RNA

Project description:Here, we describe an approach to enrich newly transcribed RNAs from primary mouse neurons using 4-thiouridine (s4U) metabolic labeling and solid phase chemistry. This one-step enrichment procedure captures s4U-RNA by using highly efficient methane thiosulfonate (MTS) chemistry in an immobilized format. Like solution-based methods, this solid-phase enrichment can distinguish mature RNAs (mRNA) with differential stability, and can be used to reveal transient RNAs such as enhancer RNAs (eRNAs) and primary microRNAs (pri-miRNAs) from short metabolic labeling. Most importantly, the efficiency of this solid-phase chemistry made possible the first large scale measurements of RNA polymerase II (RNAPII) elongation rates in mouse cortical neurons. Thus, our approach provides the means to study regulation of RNA metabolism in specific tissue contexts as a means to better understand gene expression in vivo.

2018-07-19 | GSE110951 | GEO

Total Synthesis of Scytonemide A Employing Weinreb AM Solid-Phase Resin.

Project description:The human 20S proteasome inhibitor scytonemide A (1), a macrocyclic imine originally isolated from the cyanobacterium Scytonema hofmanni, was synthesized via a biomimetic solid-phase peptide synthesis (SPPS) approach employing the Weinreb AM resin. Utilizing this approach, cyclization of the protected heptapeptide via formation of the imine bond occurred spontaneously upon cleavage from the resin in the presence of a reducing agent and subsequent aqueous workup. The final deprotection step necessary to produce the natural product was accomplished under slightly basic conditions, facilitating cleavage of the silyl ether group while leaving the macrocycle intact. Purification of the synthetic scytonemide A was accomplished via normal-phase flash column chromatography, potentially facilitating larger scale preparation of the compound necessary for future mechanistic and SAR studies. The structure of the target compound was confirmed by NMR spectroscopy, which also shed light on differences in the spectroscopic data obtained for the synthetic and natural scytonemide A samples for some of the amide and alcohol signals in the 1H NMR spectrum.

| S-EPMC5866229 | biostudies-literature

Current ADC Linker Chemistry.

Project description:The list of ADCs in the clinic continues to grow, bolstered by the success of first two marketed ADCs: ADCETRIS® and Kadcyla®. Currently, there are 40 ADCs in various phases of clinical development. However, only 34 of these have published their structures. Of the 34 disclosed structures, 24 of them use a linkage to the thiol of cysteines on the monoclonal antibody. The remaining 10 candidates utilize chemistry to surface lysines of the antibody. Due to the inherent heterogeneity of conjugation to the multiple lysines or cysteines found in mAbs, significant research efforts are now being directed toward the production of discrete, homogeneous ADC products, via site-specific conjugation. These site-specific conjugations may involve genetic engineering of the mAb to introduce discrete, available cysteines or non-natural amino acids with an orthogonally-reactive functional group handle such as an aldehyde, ketone, azido, or alkynyl tag. These site-specific approaches not only increase the homogeneity of ADCs but also enable novel bio-orthogonal chemistries that utilize reactive moieties other than thiol or amine. This broadens the diversity of linkers that can be utilized which will lead to better linker design in future generations of ADCs.

| S-EPMC4596905 | biostudies-literature

Solid phase chemistry to covalently and reversibly capture thiolated RNA.

| S-EPMC6101502 | biostudies-literature

Acylsulfonamide safety-catch linker: promise and limitations for solid-phase oligosaccharide synthesis.

Project description:Safety-catch linkers are useful for solid-phase oligosaccharide synthesis as they are orthogonal to many common protective groups. A new acylsulfonamide safety-catch linker was designed, synthesized and employed during glycosylations using an automated carbohydrate synthesizer. The analysis of the cleavage products revealed shortcomings for oligosaccharide synthesis.

| S-EPMC3511041 | biostudies-literature

Employing Solid Phase Microextraction as Extraction Tool for Pesticide Residues in Traditional Medicinal Plants.

Project description:HS-SPME was optimised using blank plant sample for analysis of organochlorine pesticides (OCPs) of varying polarities in selected medicinal plants obtained from northern part of Botswana, where OCPs such as DDT and endosulfan have been historically applied to control disease carrying vectors (mosquitos and tsetse fly). The optimised SPME parameters were used to isolate analytes from root samples of five medicinal plants obtained from Maun and Kasane, Botswana. The final analytes determination was done with a gas chromatograph equipped with GC-ECD and analyte was confirmed using electron ionisation mass spectrometer (GC-MS). Dieldrin was the only pesticide detected and confirmed with MS in the Terminalia sericea sample obtained from Kasane. The method was validated and the analyte recoveries ranged from 69.58 ± 7.20 to 113 ± 15.44%, with RSDs ranging from 1.19 to 17.97%. The method indicated good linearity (R2 > 0.9900) in the range of 2 to 100?ng?g-1. The method also proved to be sensitive with low limits of detection (LODs) ranging from 0.48 ± 0.16 to 1.50 ± 0.50?ng?g-1. It can be concluded that SPME was successfully utilized as a sampling and extraction tool for pesticides of diverse polarities in root samples of medicinal plants.

| S-EPMC5048045 | biostudies-literature

Solid phase chemistry to covalently and reversibly capture thiolated RNA

Project description:Solid phase chemistry to covalently and reversibly capture thiolated RNA

| PRJNA435267 | ENA

A solid-phase compatible silane-based cleavable linker enables custom isobaric quantitative chemoproteomics

Project description:Only ~4% of the human proteome has been drugged by FDA approved molecules. Consequently, closing this druggability gap is a central focus of mass spectrometry chemoproteomics screening platforms. Despite increasingly widespread adoption, established chemoproteomic platforms fall short of achieving comprehensive proteome-wide structure activity relationship (SAR) maps for two key reasons: (1) time consuming and cumbersome sample preparation workflows and (2) and low throughput sample acquisition. Here we report the silane-based Cleavable Linkers for Isotopically-labeled Proteomics (sCLIP) method. sCLIP streamlines sample preparation with unparalleled early-stage isobaric labeling and sample pooling, allowing for increased sample throughput via customized low cost 6-plex sample multiplexing. The sCLIP method is distinguished by its unprecedented click-assembled isobaric tags, in which the reporter group is encoded in the sCLIP capture reagent and balancer in the pan cysteine-reactive probe. When paired with a custom FragPipe data analysis workflow and applied to cysteine-reactive fragment screens, sCLIP proteomics revealed established and unprecedented cysteine-ligand pairs, including those labeled by covalent-reversible electrophilic modalities.

2023-09-20 | PXD040696 | Pride

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