Browse
Submit Data
Databases
API
Help

Dataset Information

32 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

One-pot isomerization-cross metathesis-reduction (ICMR) synthesis of lipophilic tetrapeptides.

ABSTRACT: An efficient, versatile and rapid method toward homologue series of lipophilic tetrapeptide derivatives (herein, the opioid peptides H-TIPP-OH and H-DIPP-OH) is reported. High atom economy and a minimal number of synthetic steps resulted from a one-pot tandem isomerization-cross metathesis-reduction sequence (ICMR), applicable both in solution and solid phase methodology. The broadly applicable synthesis proceeds with short reaction times and simple work-up, as illustrated in this work for alkylated opioid tetrapeptides.

SUBMITTER: Jida M

PROVIDER: S-EPMC4140390 | biostudies-literature |

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Similar Datasets

A phosphate tether-mediated, one-pot, sequential ring-closing metathesis/cross-metathesis/chemoselective hydrogenation protocol.

Project description:A versatile three-step, one-pot, sequential reaction protocol involving ring-closing metathesis, cross-metathesis, and chemoselective hydrogenation is reported. This phosphate tether-mediated process occurs without intermediate isolation, is chemoselective, and is governed by stereoelectronic properties innate to phosphate tethers, which ultimately act to preserve the integrity of the bisallylic, bicyclic phosphate for subsequent nucleophilic additions. Overall, this process can be used to efficiently generate advanced polyol synthons.

| S-EPMC3858481 | biostudies-literature

Synthesis of Substituted Benzaldehydes via a Two-Step, One-Pot Reduction/Cross-Coupling Procedure.

Project description:The synthesis of functionalized (benz)aldehydes, via a two-step, one-pot procedure, is presented. The method employs a stable aluminum hemiaminal as a tetrahedral intermediate, protecting a latent aldehyde, making it suitable for subsequent cross-coupling with (strong nucleophilic) organometallic reagents, leading to a variety of alkyl and aryl substituted benzaldehydes. This very fast methodology also facilitates the effective synthesis of a 11C radiolabeled aldehyde. Aluminum-ate complexes enable transmetalation of alkyl fragments onto palladium and subsequent cross-coupling.

| S-EPMC6558639 | biostudies-literature

One-pot synthesis of polyrotaxanes via acyclic diene metathesis polymerization of supramolecular monomers.

Project description:A one-pot synthesis of polyrotaxanes has been developed. The method employs a supramolecular monomer comprising a polymerizable ammonium salt and crown ether, in combination with dynamic ADMet polymerization. Ultimately, highly efficient complexation, polymerization, and end-capping were accomplished in a single operation to yield polyrotaxanes with M(w) up to 19.3 kDa and >80% of the repeat units being complexed.

| S-EPMC3236677 | biostudies-literature

Synthesis of caeliferins, elicitors of plant immune responses: accessing lipophilic natural products via cross metathesis.

Project description:A cross metathesis (CM)-based synthesis of the caeliferins, a family of sulfooxy fatty acids that elicit plant immune responses, is reported. Unexpectedly, detailed NMR spectroscopic and mass spectrometric analyses of CM reaction mixtures revealed extensive isomerization and homologation of starting materials and products. It is shown that the degree of isomerization and homologation in CM strongly correlates with substrate chain length and lipophilicity. Side-product suppression requires appropriate catalyst selection and use of 1,4-benzoquinone as a hydride scavenger.

| S-EPMC3216471 | biostudies-literature

Pot economy and one-pot synthesis.

Project description:The one-pot synthesis of a target molecule in the same reaction vessel is widely considered to be an efficient approach in synthetic organic chemistry. In this review, the characteristics and limitations of various one-pot syntheses of biologically active molecules are explained, primarily involving organocatalytic methods as key tactics. Besides catalysis, the pot-economy concepts presented herein are also applicable to organometallic and organic reaction methods in general.

| S-EPMC5529999 | biostudies-other

One-pot synthesis of (-)-Ambrox.

Project description:(-)-Ambrox is recognised as the prototype of all ambergris odorants. Widely used in perfumery, (-)-Ambrox is an important ingredient due to its unique scent and excellent fixative function. An environmentally friendly and practical preparation of (-)-Ambrox is still unavailable at present although a lot of attention has been paid to this hot research topic for many years. A one-pot synthesis of (-)-Ambrox was studied starting from (-)-sclareol through oxidation with hydrogen peroxide in the presence of a quaternary ammonium phosphomolybdate catalyst {[C5H5NC16H33] [H2PMo12O40]}, which gave the product a 20% overall yield.

| S-EPMC5007644 | biostudies-literature

Toward the Identification of Novel Antimicrobial Agents: One-Pot Synthesis of Lipophilic Conjugates of N-Alkyl d- and l-Iminosugars.

Project description:In the effort to improve the antimicrobial activity of iminosugars, we report the synthesis of lipophilic iminosugars 10a-b and 11a-b based on the one-pot conjugation of both enantiomeric forms of N-butyldeoxynojirimycin (NBDNJ) and N-nonyloxypentyldeoxynojirimycin (NPDNJ) with cholesterol and a succinic acid model linker. The conjugation reaction was tuned using the established PS-TPP/I2/ImH activating system, which provided the desired compounds in high yields (94-96%) by a one-pot procedure. The substantial increase in the lipophilicity of 10a-b and 11a-b is supposed to improve internalization within the bacterial cell, thereby potentially leading to enhanced antimicrobial properties. However, assays are currently hampered by solubility problems; therefore, alternative administration strategies will need to be devised.

| S-EPMC7699595 | biostudies-literature

One-pot synthesis of brush-like polymers via integrated ring-opening metathesis polymerization and polymerization of amino acid N-carboxyanhydrides.

Project description:We report here the integration of ring-opening metathesis polymerization (ROMP) and ring-opening polymerization of the amino acid N-carboxyanhydride (NCA) to allow facile synthesis of brush-like polymers containing polypeptide as the brush side chains. ROMP of N-trimethylsilyl norbornenes rendered the preparation of poly(norbornene)s bearing pendant N-TMS groups. With no need to purify the resulting polymers, such macromolecular initiators could subsequently initiate controlled NCA polymerizations. Brush-like poly(norbornene)s with grafted polypeptides or block copolypeptides were readily obtained with controlled molecular weights and narrow molecular weight distributions. Because numerous ROMP and NCA monomers are widely available, this novel polymerization technique will allow easy access to numerous brush-like hybrid macromolecules with unprecedented properties and broad applications.

| S-EPMC3222154 | biostudies-literature

Self-Assembly of Disorazole?C1 through a One-Pot Alkyne Metathesis Homodimerization Strategy.

Project description:Alkyne metathesis is increasingly explored as a reliable method to close macrocyclic rings, but there are no prior examples of an alkyne-metathesis-based homodimerization approach to natural products. In this approach to the cytotoxic C2 -symmetric marine-derived bis(lactone) disorazole?C1, a highly convergent, modular strategy is employed featuring cyclization through an ambitious one-pot alkyne cross-metathesis/ring-closing metathesis self-assembly process.

| S-EPMC4902119 | biostudies-literature

Self-Assembly of Disorazole C1 through a One-Pot Alkyne Metathesis Homodimerization Strategy.

Project description:Alkyne metathesis is increasingly explored as a reliable method to close macrocyclic rings, but there are no prior examples of an alkyne-metathesis-based homodimerization approach to natural products. In this approach to the cytotoxic C2-symmetric marine-derived bis(lactone) disorazole C1, a highly convergent, modular strategy is employed featuring cyclization through an ambitious one-pot alkyne cross-metathesis/ring-closing metathesis self-assembly process.

| S-EPMC4517162 | 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