Immobilization of glycoenzymes by means of their glycosidic components

Marek, M.; Jarý, J.; Valentová, Olga; Vodrážka, Z.

doi:10.1007/bf01386357

Cited by 20 publications

(10 citation statements)

References 11 publications

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“…In an early report of enzyme immobilization, Marek and co-workers enhanced the catalytic activity of glucose oxidase by binding it on the surface of the modified glycidyl methacrylate polymers through Ugi-4CR approach. 128 For this purpose, the glycoenzyme was reacted with periodate to prepare aldehyde groups in the glycosidic part and then participated in Ugi-4CR with amino-functionalized glycidyl methacrylate polymers, excess acetic acid and cyclohexyl isocyanide. Notably, the Ugi product showed higher activity than those products which prepared by the direct binding between the aldehyde groups and the amino groups of the polymeric carrier.…”

Section: Acs Combinatorial Sciencementioning

confidence: 99%

Materials Functionalization with Multicomponent Reactions: State of the Art

Afshari

Shaabani

2018

ACS Comb. Sci.

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The emergence of neoteric synthetic routes for materials functionalization is an interesting phenomenon in materials chemistry. In particular, the union of materials chemistry with multicomponent reactions (MCRs) opens a new avenue leading to the realm of highly innovative functionalized architectures with unique features. MCRs have recently been recognized as considerable part of the synthetic chemist's toolbox due to their great efficiency, inherent molecular diversity, atom and pot economy along with operational simplicity. Also, MCRs can improve E-factor and mass intensity as important green chemistry metrics. By rational tuning of the materials, as well as the MCRs, wide ranges of functionalized materials can be produced with tailorable properties that can play important roles in the plethora of applications. To date, there has not reported any exclusive review of a materials functionalization with MCRs. This critical review highlights the state-of-the-art on the one-pot functionalization of carbonaceous and siliceous materials, polysaccharides, proteins, enzymes, synthetic polymers, etc., via diverse kind of MCRs like Ugi, Passerini, Petasis, Khabachnik-Fields, Biginelli, and MALI reactions through covalent or noncovalent manners. Besides the complementary discussion of synthetic routes, superior properties and detailed applicability of each functionalized material in modern technologies are discussed. Our outlook also emphasizes future strategies for this unprecedented area and their use as materials for industrial implementation. With no doubt, MCRs-functionalization of materials bridges the gap between materials science domain and applied chemistry.

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Section: Acs Combinatorial Sciencementioning

confidence: 99%

Materials Functionalization with Multicomponent Reactions: State of the Art

Afshari

Shaabani

2018

ACS Comb. Sci.

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“…While the Ugi reactionh as been the objecto fe xtensive studies for the conjugation and stapling of peptides, only ah andful of publications report the use of proteins as coupling partners. [32][33][34][35][36] Most notably,a ll these strategies use the four-component version of the Ugi reaction (U-4CR); that is, they only target as ingle site at the protein surface, whether it be an amino acidr esidue (lysines or aspartates/ glutamates) or aldehydes from the glycanp ortion after periodate oxidation, and the approach necessitates the use of av ast excesso fr eagents (up to 4000 equivalents) and long reaction times (up to 4days). In addition, the absence of detailed analytical investigations precludes the conclusiont hat the Ugi reaction, and not an uncontrolled side reaction, wasi ndeed responsible for the bioconjugation.…”

Section: Introductionmentioning

confidence: 99%

“…A solution of hydroxylamine would then simply be added at the end of the reaction to regenerate the amino groups of these lysine residues that did not partake in the multicomponent reaction. While the Ugi reaction has been the object of extensive studies for the conjugation and stapling of peptides, only a handful of publications report the use of proteins as coupling partners [32–36] . Most notably, all these strategies use the four‐component version of the Ugi reaction (U‐4CR); that is, they only target a single site at the protein surface, whether it be an amino acid residue (lysines or aspartates/ glutamates) or aldehydes from the glycan portion after periodate oxidation, and the approach necessitates the use of a vast excess of reagents (up to 4000 equivalents) and long reaction times (up to 4 days).…”

Section: Introductionmentioning

confidence: 99%

Investigating Ugi/Passerini Multicomponent Reactions for the Site‐Selective Conjugation of Native Trastuzumab**

Sornay

Hessmann

Erb

et al. 2020

Chemistry A European J

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Site-selective modificationo fp roteins hasb een the object of intense studies over the past decades, especially in the therapeutic field. Prominent resultsh ave been obtained with recombinant proteins,f or which site-specific conjugation is made possible by the incorporation of particular aminoa cid residues or peptides equences. In parallel, methods for the site-selective and site-specific conjugation of native andn atural proteins are starting to thrive, allowing the controlled functionalization of various types of amino acid residues.P ursuingt he efforts in this field, we planned to develop an ew typeo fs ite-selective method, aiming at the simultaneous conjugation of two amino acid residues. We reasonedt hat this should give higher chances of developing as ite-selective strategy compared to the great majority of existing methods that solely target as ingle residue. We opted for the Ugi four-centre three-component reaction to implement this idea, with the aim of conjugating the sidechain amine and carboxylate groups of two neighbouring lysine and aspartate/glutamate. Herein,w es how that this strategyc an give access to valuable antibody conjugates bearings everald ifferent payloads;f urthermore, the approach limits the potential conjugation sites to only six on the model antibody trastuzumab.

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“…In 1983, Vodrážka et al applied Ugi reaction to immobilize glucose oxidase on a polymer carrier which was the earliest report of protein bioconjugation based on MCR ( Marek et al, 1983 ). In 2000, Lang et al reported that the Ugi reaction was used to achieve the binding of bovine serum albumin (BSA) with isocyano-modified β-D-glucosyl groups ( Ziegler et al, 2000 ).…”

Section: Strategy 2: Isocyanide-based Mcrmentioning

confidence: 99%

Isocyanides: Promising Functionalities in Bioorthogonal Labeling of Biomolecules

2021

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Isocyanides have drawn increasing attention in biological applications due to their attractive properties and unique reactivities, which can undergo various reactions, such as multicomponent reactions, α-addition reactions, [4 + 1] cycloaddition reactions, and the reaction scope keeps expanding. In addition to acting as reactants for the preparation of structurally interesting and diverse N-heterocycles or peptidomimetics, this type of functionality may be a good choice in the labeling and modulation of biomolecules due to the high biocompatibility and small size to minimize modifications on the parent molecule. It has been demonstrated that isocyanides can participate in biomolecule labeling through three strategies, including the two-component bioorthogonal reaction, multicomponent reaction, and metal chelation. Among them, the isocyanide-tetrazine reaction has been better studied recently, augmenting the potency of isocyanide as a bioorthogonal handle. This review will focus on the recent progress in isocyanide chemistry for labeling of biomolecules. Meanwhile, methods to introduce isocyano groups into biomacromolecules are also described to facilitate wider applications of this unique functionality.

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Immobilization of glycoenzymes by means of their glycosidic components

Cited by 20 publications

References 11 publications

Materials Functionalization with Multicomponent Reactions: State of the Art

Materials Functionalization with Multicomponent Reactions: State of the Art

Investigating Ugi/Passerini Multicomponent Reactions for the Site‐Selective Conjugation of Native Trastuzumab**

Isocyanides: Promising Functionalities in Bioorthogonal Labeling of Biomolecules

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