Ester coupling reactions – an enduring challenge in the chemical synthesis of bioactive natural products

Tsakos, Michail; Schaffert, Eva S.; Clement, Lise L.; Villadsen, Nikolaj L.; Poulsen, Thomas B.

doi:10.1039/c4np00106k

Cited by 172 publications

(138 citation statements)

References 266 publications

(188 reference statements)

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“…Initially, model 11 was synthesized from 9 and 10 to aid characterization of the final lignin (Scheme ). RHBL γ‐oxCA was then coupled with 10 by using EDC, Et 3 N and HOBt at RT for 24 h (Lignin general procedure D) . The resulting lignin was characterized by using HSQC NMR spectroscopy (Figure ) and compared with model 11 (Figure A).…”

Section: Resultsmentioning

confidence: 99%

“…RHBL g-oxCA was then coupled with 10 by using EDC, Et 3 Na nd HOBt at RT for 24 h( Lignin general procedure D). [53] The resulting lignin was characterizedb yu sing HSQC NMR spectroscopy ( Figure 6) and compared with model 11 (Figure 6A). Aniline 10 was selected for these studies as, on formationo ft he ligninaniline amide bond, ad istinctive change in the chemicals hift of the aniline aromatic protons was expected.…”

Section: Tempo-mediated Formation Of B-o-4 G-carboxylic Acid-substitumentioning

confidence: 99%

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Selective Primary Alcohol Oxidation of Lignin Streams from Butanol‐Pretreated Agricultural Waste Biomass

Panovic

Lancefield

Phillips³

et al. 2019

ChemSusChem

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Chemically modified lignins are important for the generation of biomass‐derived materials and as precursors to renewable aromatic monomers. A butanol‐based organosolv pretreatment has been used to convert an abundant agricultural waste product, rice husks, into a cellulose pulp and three additional product streams. One of these streams, a butanol‐modified lignin, was oxidized at the γ position to give a carboxylic acid functionalized material. Subsequent coupling of the acid with aniline aided lignin characterization and served as an example of the flexibility of this approach for grafting side chains onto a lignin core structure. The pretreatment was scaled up for use on a multi‐kilogram scale, a development that enabled the isolation of an anomeric mixture of butoxylated xylose in high purity. The robust and scalable butanosolv pretreatment has been developed further and demonstrates considerable potential for the processing of rice husks.

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Section: Resultsmentioning

confidence: 99%

Section: Tempo-mediated Formation Of B-o-4 G-carboxylic Acid-substitumentioning

confidence: 99%

Selective Primary Alcohol Oxidation of Lignin Streams from Butanol‐Pretreated Agricultural Waste Biomass

Panovic

Lancefield

Phillips³

et al. 2019

ChemSusChem

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“…An ester bond is an important structural unit that serves as key component in a number of applications . Novel fast peptide synthesis using microwave irradiation also requires a direct protocol to achieve on‐resin esterification in a robust and straightforward manner.…”

Section: Results and Methodsmentioning

confidence: 99%

Further applications of classical amide coupling reagents: Microwave‐assisted esterification on solid phase

Takayama

Hayakawa

Hinou

et al. 2018

Journal of Peptide Science

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Ester linkage (s) is a key chemical connector in organic chemistry, including natural products, peptides, and synthetic polymers. We herein describe a straightforward method for the efficient formation of ester linkage (s) on solid-phase. This method simply involves the use of amide coupling reagents under microwave irradiation. The robustness of this method relies on the use of classical solid-phase coupling reagents, heating by microwave irradiation, and a short time period, which results in high yields and the minimization of racemization.

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“…Similarly, Steglich esterification conditions can be used to couple carboxylic acids with hydroxyl groups of ligands. Like amide coupling, the carboxylic acid is pre‐activated with a carbodiimide, after which coupling agents and hydroxyl‐containing ligands are added . Steglich esterification of PEG polymers has been demonstrated by van Hest et al.…”

Section: Functional Handles On Polymersomes and Nanoparticlesmentioning

confidence: 99%

Designing Molecular Building Blocks for Functional Polymersomes

Rijpkema

Toebes

Maas

et al. 2019

Israel Journal of Chemistry

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In recent years various polymeric vesicles have been reported that show promising results for drug delivery applications, nanomotors and/or nanoreactors. These polymeric vesicles can be assembled from many different materials and various coupling reactions have been applied for functionalization of the vesicles. However, the designs reported are still rather simple, as it is challenging to mimic biological complex systems. In this review we focus on the properties of widely used hydrophobic polymers to better understand polymersome properties for various applications. Examples are shown of how researchers have used and modulated block‐copolymers and their properties to their advantage. Furthermore, an overview of possible end group functionalizations of nanoparticles is reported, giving insight in recent developments of smart nanoparticles for biomedical applications.

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Ester coupling reactions – an enduring challenge in the chemical synthesis of bioactive natural products

Cited by 172 publications

References 266 publications

Selective Primary Alcohol Oxidation of Lignin Streams from Butanol‐Pretreated Agricultural Waste Biomass

Selective Primary Alcohol Oxidation of Lignin Streams from Butanol‐Pretreated Agricultural Waste Biomass

Further applications of classical amide coupling reagents: Microwave‐assisted esterification on solid phase

Designing Molecular Building Blocks for Functional Polymersomes

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