Aqueous-Medium Selective Modification of Cysteine and Related Thiols with Tricyclic Oxygen-Heterocycles

Yoshioka, Eito; Goto, Yuya; Minato, Ikko; Miyabe, Hideto

doi:10.1055/s-0036-1588497

Cited by 4 publications

(1 citation statement)

References 3 publications

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“…After their finding that tricyclic 2 H ‐chromeme hemiketals xx have the selective reactivity toward thiophenol, [17b] they further demonstrated the utility of this reagent for the thiol‐selective modification toward bioconjugation by the use of L‐cysteine, D‐penicillamine, captopril and glutathione as sulfur‐nucleophile to afford series of 4‐sulphur substituted 4 H ‐chromenes 60 (Scheme 15). [17c] In detail, the reaction of 58 a and L‐cysteine proceeded smoothly by using MeCN‐PBS (5:1, v/v, PBS: phosphate‐buffered saline) as solvent at room temperature for 16 h to give the desired product in 97% yield. Under the standard conditions, other thiols such as D‐penicillamine, captopril and Glutathione can be also compatible to afford corresponding products in 40%‐quant yield.…”

Section: Nucleophilic Addition To 2h‐chromene Derivativesmentioning

confidence: 99%

Advancements in the Preparation of 4H‐Chromenes: An Overview

et al. 2023

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Functionalized 4H‐chromenes represent one class of the most important structural scaffolds in both synthetic and medicinal chemistry. They often appear in an arrange of biological natural products, pharmaceutical agents and drug candidates. The significance has stimulated the development of efficient methodologies for the synthesis of such compounds. In this review, a comprehensive discussion on different synthetic approaches to 4H‐chromenes has been presented with an emphasis on reaction features and mechanisms. Three main categories are outlined: 1) nucleophilic addition to 2H‐chromene derivatives, 2) 4H‐chromene ring formation involved cycloaddition or cyclization reactions, and 3) miscellaneous reactions.

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Section: Nucleophilic Addition To 2h‐chromene Derivativesmentioning

confidence: 99%

Advancements in the Preparation of 4H‐Chromenes: An Overview

et al. 2023

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Site-Specific Conjugation of Polymers to Proteins

Wang

2018

Biomacromolecules

100

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Conjugation of polymer to protein has been widely employed in therapeutics, medicine, biotechnology, and enzymatic catalysis. The synergistic effect benefits both counterparts and potentially overcomes their inherent limitations. This article reviews the strategies for the site-specific synthesis of well-defined protein-polymer conjugates, aiming to provide a toolbox for the community. First, it is essential to set a definite reactive site on the protein because the position of the reaction site can directly influence the reaction activity and the bioactivity of the protein after modification. The origins of the specific functional groups on protein include the utilization of the unique natural amino acid, mutagenesis to introduce a sole reactive amino acid, chemical modification, noncanonical amino acid incorporation, and enzyme-mediated introduction of functional groups. Second, the main conjugation methods, i.e., "grafting to" and "grafting from" methods, are summarized and compared with each other. In the "grafting to" method, a comprehensive investigation on the reactions used to attach an end functional polymer chain to a protein is conducted according to the position of the target site and its nature. In the "grafting from" method, a comparison between the commonly used controlled polymerization, i.e., atom transfer radical polymerization (ATRP) and reversible addition-fragmentation transfer (RAFT), is surveyed. Further, a special case where a noncovalent bond is adopted to link the protein and polymer together is investigated due to its high specificity and reversibility, typically biotin-(strept)avidin-based interactions and metal-mediated conjugation. Finally, applications of protein-polymer conjugates in drug delivery, biomedicine, biosensor, and the disease-related protein self-assembly are illustrated. This precise review on the conjugation of polymer chain to protein to form well-defined protein-polymer conjugates summarizes the representative strategies and may provide useful cues in the areas of biotechnology, therapeutic drugs, and biomedicine.

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