Browse
Submit Data
Databases
API
Help

Dataset Information

25 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

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

ABSTRACT: 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.

SUBMITTER: Olivier KS

PROVIDER: S-EPMC2871400 | biostudies-literature | 2010 Apr

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

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

Olivier Kevin S KS Van Nieuwenhze Michael S MS

Organic letters 20100401 8

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. ...[more]

PMID: 20232818

Similar Datasets

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

Project description: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 of β-methyllanthionine in a single batch.

| S-EPMC6542561 | 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

Diversity-Oriented Synthesis of Glycosylphosphatidylinositol Probes Based on an Orthogonally Protected Pentasaccharide.

Project description:Two glycosylphosphatidylinositol (GPI) derivatives having an alkynyl group at different positions were derived from the same orthogonally protected pentasaccharide that in turn was assembled by a convergent [3+2] glycosylation strategy. The resultant alkynylated GPIs are useful biological probes and are suitable for further modification by click reaction to obtain other GPI probes. The pentasaccharide is a versatile platform for the synthesis of various uniquely functionalized GPI probes.

| S-EPMC10132856 | biostudies-literature

Diastereoselective synthesis of cyclopentapyridazinones via radical cyclization: synthetic studies toward halichlorine.

Project description:The pyridazinone ring system serves as an excellent scaffold for the diastereoselective preparation of novel cis-fused cyclopentapyridazinones utilizing the directed 5-exo radical cyclization approach. This overall approach was successfully employed in the preparation of a functionalized aza-spirocycle.

| S-EPMC2745910 | biostudies-literature

Synthetic studies toward (+)-cortistatin A.

Project description:We describe herein the synthesis of a late-stage intermediate en route to cortistatin A. Key transformations included a Snieckus-like cascade sequence culminating in a 6?-electrocyclization, an alkylative dearomatization, and the stereoselective functionalization of the cortistatin A-ring. While the total synthesis we sought was not accomplished, the work sets the stage for several approaches to the preparation of novel analogs via diverted total synthesis.

| S-EPMC3413295 | biostudies-literature

Synthesis of peptide nucleic acid FRET probes via an orthogonally protected building block for post-synthetic labeling of peptide nucleic acids at the 5-position of uracil.

Project description:We report the design and synthesis of an orthogonally protected peptide nucleic acid (PNA) building block, Fmoc-PNA-U'-(Dde)-OH, and its use in the construction of PNA FRET probes. This building block allows for the post-synthetic attachment of reporter groups to the amino group attached to the 5-position of uracil (U) following selective deprotection of the Dde group. We illustrate the use of this building block for the synthesis of a series of FAM Cy5 donor acceptor pairs and their ability to detect a target DNA sequence.

| S-EPMC2763603 | biostudies-literature

Synthetic studies toward lapidilectine-type Kopsia alkaloids.

Project description:A rapid synthesis of the tetracyclic core of Kopsia indole alkaloids related to lapidilectine B, grandilodine C, and tenuisine A is reported. Key to the success of this route was an efficient and scalable Ugi four-component coupling to install all the necessary carbons found in the natural products.

| S-EPMC3262909 | biostudies-literature

Synthetic studies toward Mycobacterium tuberculosis sulfolipid-I.

Project description:Sulfolipid-I (SL-I) is an abundant metabolite found in the cell wall of Mycobacterium tuberculosis that is comprised of a trehalose 2-sulfate core modified with four fatty acyl substituents. The correlation of its abundance with the virulence of clinical isolates suggests a role for SL-I in pathogenesis, although its biological functions remain unknown. Here we describe the synthesis of a SL-I analogue bearing unnatural lipid substituents. A key feature of the synthesis was application of an intramolecular aglycon delivery reaction to join two differentially protected glucose monomers, one prepared with a novel alpha-selective glycosylation. The route developed for the model compound can be readily extended to the synthesis of native SL-I as well as additional analogues for use in the investigation of SL-I's functions.

| S-EPMC2735189 | biostudies-other

Synthesis of Four Orthogonally Protected Rare l-Hexose Thioglycosides from d-Mannose by C-5 and C-4 Epimerization

Project description:l-Hexoses are important components of biologically relevant compounds and precursors of some therapeuticals. However, they typically cannot be obtained from natural sources and due to the complexity of their synthesis, their commercially available derivatives are also very expensive. Starting from one of the cheapest d-hexoses, d-mannose, using inexpensive and readily available chemicals, we developed a reaction pathway to obtain two orthogonally protected l-hexose thioglycoside derivatives, l-gulose and l-galactose, through the corresponding 5,6-unsaturated thioglycosides by C-5 epimerization. From these derivatives, the orthogonally protected thioglycosides of further two l-hexoses (l-allose and l-glucose) were synthesized by C-4 epimerization. The preparation of the key intermediates, the 5,6-unsaturated derivatives, was systematically studied using various protecting groups. By the method developed, we are able to produce highly functionalized l-gulose derivatives in 9 steps (total yields: 21–23%) and l-galactose derivatives in 12 steps (total yields: 6–8%) starting from d-mannose.

| S-EPMC9182441 | biostudies-literature

Chemoenzymatic synthesis of each enantiomer of orthogonally protected 4,4-difluoroglutamic acid: a candidate monomer for chiral Bronsted acid peptide-based catalysts.

Project description:We have accomplished an asymmetric synthesis of each enantiomer of 4,4-difluoroglutamic acid. This α-amino acid has been of interest in medicinal chemistry circles. Key features of the synthesis include highly scalable procedures, a Reformatsky-based coupling reaction, and straightforward functional group manipulations to make the parent amino acid. Enantioenrichment derives from an enzymatic resolution of the synthetic material. Conversion of the optically enriched compounds to orthogonally protected forms allows for the selective formation of peptide bonds. 4,4-Difluoroglutamic acid, in a suitably protected form, is also shown to exhibit enhanced catalytic activity in both an oxidation reaction and a reduction reaction, in comparison to the analogous glutamic acid derivative.

| S-EPMC3228520 | 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