Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Preparation and reactions of N-thioformyl peptides from amino thioacids and isonitriles.

ABSTRACT: The preparation of N-thioformyl peptides from amino thioacids and isonitriles at room temperature is described.

SUBMITTER: Yuan Y

PROVIDER: S-EPMC2690959 | biostudies-literature | 2009 May

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Preparation and reactions of N-thioformyl peptides from amino thioacids and isonitriles.

Yuan Yu Y Zhu Jianglong J Li Xuechen X Wu Xiangyang X Danishefsky Samuel J SJ

Tetrahedron letters 20090501 20

The preparation of N-thioformyl peptides from amino thioacids and isonitriles at room temperature is described. ...[more]

PMID: 20161291

Similar Datasets

Coupling reactions of hindered isonitriles and hindered alkyl thioacids: Mechanistic studies.

Project description:The coupling reaction between hindered thioacids and isonitriles is developed and described. The mechanism for the formation of the thiopyruvamide products is explored, and the method is applied to a selection of substrates.

| S-EPMC2758784 | biostudies-literature

On the Preparation of Enantiomerically Pure Isonitriles from Amino Acid Esters and Peptides.

Project description:An improved method for the synthesis of enantiomerically pure isonitriles from amino acid esters and dipeptides is described.

| S-EPMC3159893 | biostudies-literature

o-Quinones formed in plant extracts. Their reactions with amino acids and peptides.

Project description:1. The reactions of amino acids and peptides with the o-quinones produced by the enzymic oxidation of chlorogenic acid and caffeic acid have been studied manometrically and spectrophotometrically. 2. Amino acids, except lysine and cysteine, react primarily through their alpha-amino groups to give red or brown products. These reactions, which compete with the polymerization of the quinones, are followed by secondary reactions that may absorb oxygen and give products with other colours. 3. The in-amino group of lysine reacts with the o-quinones in a similar way. The thiol group of cysteine reacts with the quinones, without absorbing oxygen, giving colourless products. 4. Peptides containing cysteine react with the o-quinones through their thiol group. 5. Other peptides, such as glycyl-leucine and leucylglycine, react primarily through their alpha-amino group and the overall reaction resembles that of the N-terminal amino acid except that it is quicker. 6. With some peptides, the secondary reactions differ from those that occur between the o-quinones and the N-terminal amino acids. The colours produced from carnosine resemble those produced from histidine rather than those from beta-alanine, and the reactions of prolylalanine with o-quinones are more complex than those of proline.

| S-EPMC1187763 | biostudies-other

Samarium iodide-mediated Reformatsky reactions for the stereoselective preparation of ?-hydroxy-?-amino acids: synthesis of isostatine and dolaisoleucine.

Project description:The synthesis of ?-hydroxy-?-amino acids via SmI(2)-mediated Reformatsky reactions of ?-chloroacetyloxazolidinones with aminoaldehydes is reported. Diastereoselective coupling is demonstrated to depend on the absolute configuration of the Evans chiral auxiliary employed in the reaction, allowing erythro or threo products to be obtained selectively. The potential utility of the methodology is exemplified by the facile synthesis of biologically relevant N-Boc-isostatine (2b) and N-Boc-dolaisoleucine (3c).

| S-EPMC3259735 | biostudies-literature

Preparation and wittig reactions of organotrifluoroborato phosphonium ylides.

Project description:[reaction: see text] Potassium [(trifluoroboratophenyl)methyl]triphenylphosphonium chlorides have been prepared from the corresponding benzyl chlorides and PPh3. In the presence of 1.2 equiv of K2CO3 and various aldehydes, these mixed salts are easily converted to the corresponding unsaturated organotrifluoroborates via the intermediate phosphorus ylides. A protocol for a one-pot transformation has also been developed.

| S-EPMC2556880 | biostudies-literature

Preparation and Diels-Alder reactions of 1'-heterosubsituted vinylimidazoles.

Project description:A Diels-Alder/rearrangement sequence has been pursued in our lab en route to a number of oroidin dimers. In order to access the fully substituted core of these molecules, 1',2'-disubstituted 4-vinylimidazoles were required as dienes. The preparation of a series of a 4-vinylimidazoles containing substituents on the vinyl moiety via hydroalumination/electrophilic trapping or hydrosilylation are described. These derivatives undergo Diels-Alder reactions with N-phenylmaleimide to provide the tetrahydrobenzimidazole derivatives. The cycloadducts derived from halosubstituted systems generally undergo elimination, leading to the corresponding dihydrobenzimidazole, whereas the silyl and stannyl derivatives provide the corresponding 4-substituted tetrahydrobenzimidazole.

| S-EPMC4484863 | biostudies-literature

Preparation and ring-opening reactions of N-diphenylphosphinyl vinyl aziridines.

Project description:Predominantly (E)-N-diphenylphosphinyl vinyl aziridines are prepared by a reaction of N-diphenylphosphinyl imines with ?-bromoallyllithium in the presence of freshly fused ZnCl2. These aziridines undergo a ring-opening reaction with a variety of carbon and heteronucleophiles, in good yield, and generally with good regioselectivity.

| S-EPMC3678660 | biostudies-literature

Revisiting oxytocin through the medium of isonitriles.

Project description:The reaction of thioamino acids and N-terminal peptides, mediated by hindered isonitriles and hydroxybenzotriazole, gives rise to peptide bonds. In one pathway, oxytocin was synthesized by eight such reiterative amidations. In another stereospecific track, oxytocin was constructed by native chemical ligation, wherein the two building blocks were assembled by thioacid amine amidation. The NMR spectra of oxytocin and dihydrooxytocin suggest a high level of preorganization in the latter, perhaps favoring oxidative folding.

| S-EPMC3433685 | biostudies-literature

Direct Conversion of Nitriles into Alkene "Isonitriles".

Project description:The sequenced addition of RLi to nitriles, trapping with isopropylformate, and dehydration with phosphoryl chloride provides an efficient, direct synthesis of alkene isocyanides. The one-pot sequence involves a series of carefully orchestrated steps: addition, formylation, tautomerization, and dehydration, with CuCN catalyzing a key equilibration of a formyl imine to an N-formyl enamine. The resulting aromatic alkeneisocyanides, that are otherwise challenging to synthesize, engage in an unusual [4+2]-type cycloaddition/1,3-H shift/decyanation sequence to afford substituted naphthalenes.

| S-EPMC5176577 | biostudies-literature

Binding of aromatic isonitriles to haemoglobin and myoglobin.

Project description:A series of aromatic isonitriles were synthesized and their binding to sheep haemoglobin and horse heart myoglobin was investigated. The disubstituted ligands 2,6-dimethylphenylisonitrile and 2,6-diethylphenylisonitrile were found to bind to horse-heart myoglobin with affinities ranging from 500 to 5000 times greater than that of ethylisonitrile (4.6 x 10(-6) M) which has been the tightest binding isonitrile ligand for myoglobin thus far reported. The tight binding was not found to vary significantly with pH or temperature. An explanation for the unexpectedly high affinity is offered in terms of the electronic structure of aromatic isonitriles.

| S-EPMC1148465 | biostudies-other

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