Browse
Submit Data
Databases
API
Help

Dataset Information

23 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Scalable Synthesis of Orthogonally Protected ?-Methyllanthionines by Indium(III)-Mediated Ring Opening of Aziridines.

ABSTRACT: Lantibiotics are a class of peptide antibiotics with activity against most Gram-positive bacteria. Lanthionine (Lan) and ?-MeLan are unusual thioether-bridged, non-proteinogenic amino acids, which are characteristic features of lantibiotics. In this paper, we report the facile stereoselective synthesis of ?-methyllanthionines with orthogonal protection by nucleophilic ring opening of aziridines. This method leads to an expedient access to ?-methyllanthionines and allows production of over 30 g of ?-methyllanthionine in a single batch.

SUBMITTER: Li Z

PROVIDER: S-EPMC6542561 | biostudies-literature | 2019 Apr

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Scalable Synthesis of Orthogonally Protected β-Methyllanthionines by Indium(III)-Mediated Ring Opening of Aziridines.

Li Ziran Z Gentry Zachary Z Murphy Brennan B VanNieuwenhze Michael S MS

Organic letters 20190311 7

Lantibiotics are a class of peptide antibiotics with activity against most Gram-positive bacteria. Lanthionine (Lan) and β-MeLan are unusual thioether-bridged, non-proteinogenic amino acids, which are characteristic features of lantibiotics. In this paper, we report the facile stereoselective synthesis of β-methyllanthionines with orthogonal protection by nucleophilic ring opening of aziridines. This method leads to an expedient access to β-methyllanthionines and allows production of over 30 g o ...[more]

PMID: 30855974

Similar Datasets

Synthesis of ?-substituted tryptamines by regioselective ring opening of aziridines.

Project description:Functionalized tryptamines are targets of interest for development as small molecule therapeutics. The ring opening of aziridines with indoles is a powerful method for tryptamine synthesis if site selectivity can be controlled. 4-Nitrobenzyl carbamate (PNZ)-protected aziridines undergo regioselective ring opening to produce ?-substituted tryptamines for a series of indoles. The PNZ-protected tryptamines can be further manipulated by PNZ removal under mild conditions.

| S-EPMC4930112 | biostudies-literature

Ammonium Salt-Catalyzed Ring-Opening of Aryl-Aziridines with β-Keto Esters.

Project description:We herein report an ammonium salt-catalyzed protocol for the regioselective ring opening of aryl-aziridines with β-keto esters. The reaction gives access to a variety of highly functionalized target molecules with two consecutive stereo-genic centers and can be rendered enantioselective (up to e.r. = 91:9) by using bifunctional chiral ammonium salt catalysts.

| S-EPMC7508174 | biostudies-literature

Synthetic studies toward the mannopeptimycins: synthesis of orthogonally protected beta-hydroxyenduracididines.

Project description:The asymmetric synthesis of the nonproteinogenic amino acids (2S,3S,4'S)-beta-hydroxyenduracididine 3 and (2R,3S,4'S)-beta-hydroxyenduracididine 4 in orthogonally protected form in 15 total steps from Garner's aldehyde is reported. The former and N-glycosylated form of the latter are found in the glycopeptide antibiotic mannopeptimycin.

| S-EPMC2871400 | 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

Ammonium Salt-Catalyzed Ring-Opening of Aryl-Aziridines with ?-Keto Esters

Project description:We herein report an ammonium salt-catalyzed protocol for the regioselective ring opening of aryl-aziridines with ?-keto esters. The reaction gives access to a variety of highly functionalized target molecules with two consecutive stereo-genic centers and can be rendered enantioselective (up to e.r. = 91:9) by using bifunctional chiral ammonium salt catalysts.

| S-EPMC7116117 | biostudies-literature

Stereoselective synthesis of complex polycyclic aziridines: use of the Bronsted acid-catalyzed aza-Darzens reaction to prepare an orthogonally protected mitomycin C intermediate with maximal convergency.

Project description:A concise synthesis of a highly functionalized intermediate lacking only C10 of the mitomycin backbone is described. The key to this development is the Brønsted acid-catalyzed aza-Darzens reaction used to forge the cis-aziridine. Additionally an oxidative ketalization fortuitously occurs during the quinone-enamine coupling step, leading to an orthogonally protected hydroquinone.

| S-EPMC3334326 | biostudies-literature

Copper-Catalyzed Ring-Opening Reactions of Alkyl Aziridines with B2pin2: Experimental and Computational Studies.

Project description:The possibility to form new C-B bonds with aziridines using diboron derivatives continues to be a particularly challenging field in view of the direct preparation of functionalized β-aminoboronates, which are important compounds in drug discovery, being a bioisostere of β-aminoacids. We now report experimental and computational data that allows the individuation of the structural requisites and of reaction conditions necessary to open alkyl aziridines using bis(pinacolate)diboron (B2pin2) in a regioselective nucleophilic addition reaction under copper catalysis.

| S-EPMC8659106 | biostudies-literature

Modular continuous flow synthesis of orthogonally protected 6-deoxy glucose glycals.

Project description:An efficient, modular continuous flow process towards accessing two orthogonally protected glycals is described with the development of reaction conditions for several common protecting group additions in flow, including the addition of benzyl, naphthylmethyl and tert-butyldimethylsilyl ethers. The process affords the desired target compounds in 57-74% overall yield in just 21-37 minutes of flow time. Furthermore, unlike batch conditions, the flow processes avoided the need for active cooling to prevent unwanted exotherms and required shorter reaction times.

| S-EPMC7289173 | biostudies-literature

Cationic indium catalysts for ring opening polymerization: tuning reactivity with hemilabile ligands.

Project description:This is a comprehensive study of the effects of rationally designed hemilabile ligands on the stability, reactivity, and change in catalytic behavior of indium complexes. We report cationic alkyl indium complexes supported by a family of hemi-salen type ligands bearing hemilabile thiophenyl (2a), furfuryl (2b) and pyridyl (2c) pendant donor arms. Shelf-life and stability of these complexes followed the trend 2a < 2b < 2c, showing direct correlation to the affinity of the pendant donor group to the indium center. Reactivity towards polymerization of epichlorohydrin and cyclohexene oxide followed the trend 2a > 2b > 2c with control of polymerization following an inverse relationship to reactivity. Surprisingly, 2c polymerized racemic lactide without an external initiator, likely through an alkyl-initiated coordination-insertion mechanism.

| S-EPMC8159295 | biostudies-literature

Synthesis and ring openings of cinnamate-derived N-unfunctionalised aziridines.

Project description:tert-Butyl cinnamates are aziridinated with high trans-selectivity by an N-N ylide generated in situ from N-methylmorpholine and O-diphenylphosphinyl hydroxylamine. The resulting N-unfunctionalised aziridines are shown to be versatile synthetic building blocks that undergo highly selective ring-opening reactions with a wide range of nucleophiles.

| S-EPMC3511008 | 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