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Journal articles on the topic 'Bioconjugation reaction'

Author: Grafiati

Published: 9 March 2023

Last updated: 10 March 2023

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1

Flood, Dillon T., Jordi C. J. Hintzen, Kyle W. Knouse, David E. Hill, Chenxi Lu, Philip A. Cistrone, Jason S. Chen, Takanori Otomo, and Philip E. Dawson. "Selenomethionine as an expressible handle for bioconjugations." Proceedings of the National Academy of Sciences 118, no. 8 (February 18, 2021): e2005164118. http://dx.doi.org/10.1073/pnas.2005164118.

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Site-selective chemical bioconjugation reactions are enabling tools for the chemical biologist. Guided by a careful study of the selenomethionine (SeM) benzylation, we have refined the reaction to meet the requirements of practical protein bioconjugation. SeM is readily introduced through auxotrophic expression and exhibits unique nucleophilic properties that allow it to be selectively modified even in the presence of cysteine. The resulting benzylselenonium adduct is stable at physiological pH, is selectively labile to glutathione, and embodies a broadly tunable cleavage profile. Specifically, a 4-bromomethylphenylacetyl (BrMePAA) linker has been applied for efficient conjugation of complex organic molecules to SeM-containing proteins. This expansion of the bioconjugation toolkit has broad potential in the development of chemically enhanced proteins.

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2

Tantipanjaporn, Ajcharapan, and Man-Kin Wong. "Development and Recent Advances in Lysine and N-Terminal Bioconjugation for Peptides and Proteins." Molecules 28, no. 3 (January 21, 2023): 1083. http://dx.doi.org/10.3390/molecules28031083.

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The demand for creation of protein diversity and regulation of protein function through native protein modification and post-translational modification has ignited the development of selective chemical modification methods for peptides and proteins. Chemical bioconjugation offers selective functionalization providing bioconjugates with desired properties and functions for diverse applications in chemical biology, medicine, and biomaterials. The amino group existing at the lysine residue and N-terminus of peptides and proteins has been extensively studied in bioconjugation because of its good nucleophilicity and high surface exposure. Herein, we review the development of chemical methods for modification of the amino groups on lysine residue and N-terminus featuring excellent selectivity, mild reaction conditions, short reaction time, high conversion, biocompatibility, and preservation of protein integrity. This review is organized based on the chemoselectivity and site-selectivity of the chemical bioconjugation reagents to the amino acid residues aiming to provide guidance for the selection of appropriate bioconjugation methods.

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3

Choi, Eun Joung, Dongwook Jung, Jong-Seo Kim, Yan Lee, and B. Moon Kim. "Chemoselective Tyrosine Bioconjugation through Sulfate Click Reaction." Chemistry - A European Journal 24, no. 43 (July 18, 2018): 10948–52. http://dx.doi.org/10.1002/chem.201802380.

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4

Miyabe, Hideto, Eito Yoshioka, Yuya Goto, and Ikko Minato. "Aqueous-Medium Selective Modification of Cysteine and Related Thiols with Tricyclic Oxygen-Heterocycles." Synthesis 49, no. 21 (July 25, 2017): 4887–92. http://dx.doi.org/10.1055/s-0036-1588497.

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The utility of tricyclic oxygen-heterocycles as a reagent for the thiol-selective modification toward bioconjugation was demonstrated by the use of l-cysteine, homocysteine, captopril, and glutathione as a nucleophile having a thiol group. These trapping reactions proceeded under the mild and aqueous reaction conditions.

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5

Draganov, Alexander B., Ke Wang, Jalisa Holmes, Krishna Damera, Danzhu Wang, Chaofeng Dai, and Binghe Wang. "Click with a boronic acid handle: a neighboring group-assisted click reaction that allows ready secondary functionalization." Chemical Communications 51, no. 82 (2015): 15180–83. http://dx.doi.org/10.1039/c5cc05890b.

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6

Hörner, S., C. Uth, O. Avrutina, H. Frauendorf, M. Wiessler, and H. Kolmar. "Combination of inverse electron-demand Diels–Alder reaction with highly efficient oxime ligation expands the toolbox of site-selective peptide conjugations." Chemical Communications 51, no. 55 (2015): 11130–33. http://dx.doi.org/10.1039/c5cc03434e.

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7

Song, Chunlan, Kun Liu, Zhongjie Wang, Bo Ding, Shengchun Wang, Yue Weng, Chien-Wei Chiang, and Aiwen Lei. "Electrochemical oxidation induced selective tyrosine bioconjugation for the modification of biomolecules." Chemical Science 10, no. 34 (2019): 7982–87. http://dx.doi.org/10.1039/c9sc02218j.

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8

Montalvan-Sorrosa, D., J. L. González-Solis, J. Mas-Oliva, and R. Castillo. "Filamentous virus decoration with gold nanoparticles: global fingerprints of bionanocomposites acquired with SERS." RSC Adv. 4, no. 100 (2014): 57329–36. http://dx.doi.org/10.1039/c4ra10656c.

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9

Ramos-Tomillero, Iván, Gema Pérez-Chacon, Beatriz Somovilla-Crespo, Francisco Sánchez-Madrid, Carmen Cuevas, Juan Manuel Zapata, Juan Manuel Domínguez, Hortensia Rodríguez, and Fernando Albericio. "From Ugi Multicomponent Reaction to Linkers for Bioconjugation." ACS Omega 5, no. 13 (March 23, 2020): 7424–31. http://dx.doi.org/10.1021/acsomega.0c00099.

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10

Hu, Xianglong, Xueqian Zhao, Benzhao He, Zheng Zhao, Zheng Zheng, Pengfei Zhang, Xiujuan Shi, et al. "A Simple Approach to Bioconjugation at Diverse Levels: Metal-Free Click Reactions of Activated Alkynes with Native Groups of Biotargets without Prefunctionalization." Research 2018 (December 12, 2018): 1–12. http://dx.doi.org/10.1155/2018/3152870.

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The efficient bioconjugation of functional groups/molecules to targeted matrix and bio-related species drives the great development of material science and biomedicine, while the dilemma of metal catalysis, uneasy premodification, and limited reaction efficiency in traditional bioconjugation has restricted the booming development to some extent. Here, we provide a strategy for metal-free click bioconjugation at diverse levels based on activated alkynes. As a proof-of-concept, the abundant native groups including amine, thiol, and hydroxyl groups can directly react with activated alkynes without any modification in the absence of metal catalysis. Through this strategy, high-efficient modification and potential functionalization can be achieved for natural polysaccharide, biocompatible polyethylene glycol (PEG), synthetic polymers, cell penetrating peptide, protein, fast whole-cell mapping, and even quick differentiation and staining of Gram-positive bacteria, etc. Therefore, current metal-free click bioconjugation strategy based on activated alkynes is promising for the development of quick fluorescence labeling and functional modification of many targets and can be widely applied towards the fabrication of complex biomaterials and future in vivo labeling and detection.

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11

Tang, T. M. Simon, Davide Cardella, Alexander J. Lander, Xuefei Li, Jorge S. Escudero, Yu-Hsuan Tsai, and Louis Y. P. Luk. "Use of an asparaginyl endopeptidase for chemo-enzymatic peptide and protein labeling." Chemical Science 11, no. 23 (2020): 5881–88. http://dx.doi.org/10.1039/d0sc02023k.

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12

Cistrone, Philip A., Anouk Dirksen, Sampat Ingale, and Philip E. Dawson. "Scandium(III) Triflate as a Lewis Acid Catalyst of Oxime Ligation." Australian Journal of Chemistry 73, no. 4 (2020): 377. http://dx.doi.org/10.1071/ch20042.

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Imine-forming reactions are widely applicable in bioconjugation owing to their high chemoselectivity. The ligation of a ketone or aldehyde with an aminooxy functional group to form a physiologically stable oxime bond is often used to link complex and precious biomolecules. Although the reaction proceeds modestly in acidic solution, the abundance of protonated carbonyl species at pH 7 limits its utility in many biological applications. The use of nucleophilic aryl amines, such as aniline or a phenylenediamine, allows a high population of protonated Schiff base to undergo transimination to the oxime product. Although this method affords significant enhancements at low pH, reactions can still be sluggish at neutral pH, especially with ketones such as acetophenone that are commonly used in bioconjugation. Here, we employ scandium(iii) trifluromethanesulfonate (triflate) (Sc(OTf)3), a uniquely water-stable Lewis acid, as a co-catalyst with ortho-phenylenediamine in the oxime ligation to yield up to an order of magnitude rate enhancement over the catalysts when applied individually.

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13

Han, Ming-Jie, Qing-tao He, Mengyi Yang, Chao Chen, Yirong Yao, Xiaohong Liu, Yuchuan Wang, et al. "Single-molecule FRET and conformational analysis of beta-arrestin-1 through genetic code expansion and a Se-click reaction." Chemical Science 12, no. 26 (2021): 9114–23. http://dx.doi.org/10.1039/d1sc02653d.

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A facile bioconjugation reaction for site-specific protein modification was developed for smFRET measurement, which detected the subtle but important conformational change of the β-arrestin/GPCR complex for the first time.

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14

Shen, Kun, and Qiu Wang. "Copper-catalyzed aminoalkynylation of alkenes with hypervalent iodine reagents." Chemical Science 8, no. 12 (2017): 8265–70. http://dx.doi.org/10.1039/c7sc03420b.

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A copper-catalyzed aminoalkynylation reaction of alkenes is developed for construction of diverse azaheterocycles and installation of an alkyne group in one step, presenting broad applications in synthesis, bioconjugation, and molecular imaging.

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15

Jouanno, Laurie-Anne, Arnaud Chevalier, Nawal Sekkat, Nicolas Perzo, Hélène Castel, Anthony Romieu, Norbert Lange, Cyrille Sabot, and Pierre-Yves Renard. "Kondrat’eva Ligation: Diels–Alder-Based Irreversible Reaction for Bioconjugation." Journal of Organic Chemistry 79, no. 21 (October 27, 2014): 10353–66. http://dx.doi.org/10.1021/jo501972m.

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16

Ban, Hitoshi, Julia Gavrilyuk, and Carlos F. Barbas. "Tyrosine Bioconjugation through Aqueous Ene-Type Reactions: A Click-Like Reaction for Tyrosine." Journal of the American Chemical Society 132, no. 5 (February 10, 2010): 1523–25. http://dx.doi.org/10.1021/ja909062q.

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17

Decuypère, Elodie, Lucie Plougastel, Davide Audisio, and Frédéric Taran. "Sydnone–alkyne cycloaddition: applications in synthesis and bioconjugation." Chem. Commun. 53, no. 84 (2017): 11515–27. http://dx.doi.org/10.1039/c7cc06405e.

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This feature article aims at providing an overview of the recent developments in sydnone–alkyne cycloadditions. Particular attention has been focused on the strategies for achieving high regiocontrol, milder reaction conditions and applications in the field of click and biorthogonal chemistry.

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18

Addy, Partha Sarathi, Sarah B. Erickson, James S. Italia, and Abhishek Chatterjee. "A Chemoselective Rapid Azo-Coupling Reaction (CRACR) for Unclickable Bioconjugation." Journal of the American Chemical Society 139, no. 34 (August 16, 2017): 11670–73. http://dx.doi.org/10.1021/jacs.7b05125.

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19

Li, Gai-Li, Karen Ka-Yan Kung, Lan Zou, Hiu-Chi Chong, Yun-Chung Leung, Ka-Hing Wong, and Man-Kin Wong. "Multifunctional bioconjugation by Morita–Baylis–Hillman reaction in aqueous medium." Chemical Communications 48, no. 29 (2012): 3527. http://dx.doi.org/10.1039/c2cc17116c.

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20

Joshi, Neel S., Leanna R. Whitaker, and Matthew B. Francis. "A Three-Component Mannich-Type Reaction for Selective Tyrosine Bioconjugation." Journal of the American Chemical Society 126, no. 49 (December 2004): 15942–43. http://dx.doi.org/10.1021/ja0439017.

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21

Tejado, Alvaro, Miro Antal, Xiaojun Liu, and Theo G. M. van de Ven. "Wet Cross-Linking of Cellulose Fibers via a Bioconjugation Reaction." Industrial & Engineering Chemistry Research 50, no. 10 (May 18, 2011): 5907–13. http://dx.doi.org/10.1021/ie1023589.

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22

Kaiser, Dustin, Johan M. Winne, Maria Elena Ortiz-Soto, Jürgen Seibel, Thien A. Le, and Bernd Engels. "Mechanistical Insights into the Bioconjugation Reaction of Triazolinediones with Tyrosine." Journal of Organic Chemistry 83, no. 17 (July 13, 2018): 10248–60. http://dx.doi.org/10.1021/acs.joc.8b01445.

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23

Dinand, E., M. Zloh, and S. Brocchini. "Competitive Reactions During Amine Addition to cis-Aconityl Anhydride." Australian Journal of Chemistry 55, no. 7 (2002): 467. http://dx.doi.org/10.1071/ch02092.

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Amine addition to cis-aconityl anhydride has been used to prepare monomers needed to make water-soluble polymers that are being developed for biomedical applications. Unfortunately competitive decarboxylation, double bond isomerization, and hydrolysis reactions of cis-aconityl anhydride have been observed during monomer synthesis. Since cis-aconityl anhydride has also been used for bioconjugation applications, these deleterious side reactions should be accounted for. Reactions and product profiles of cis-aconityl anhydride with amines and amino acids in aqueous and organic media are described. The side reactions could be avoided with weakly nucleophilic aromatic amines and by the interfacial reaction of glycine with cis-aconityl anhydride.

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24

Tsao, Kelvin K., Ann C. Lee, Karl É. Racine, and Jeffrey W. Keillor. "Site-Specific Fluorogenic Protein Labelling Agent for Bioconjugation." Biomolecules 10, no. 3 (February 28, 2020): 369. http://dx.doi.org/10.3390/biom10030369.

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Many clinically relevant therapeutic agents are formed from the conjugation of small molecules to biomolecules through conjugating linkers. In this study, two novel conjugating linkers were prepared, comprising a central coumarin core, functionalized with a dimaleimide moiety at one end and a terminal alkyne at the other. In our first design, we developed a protein labelling method that site-specifically introduces an alkyne functional group to a dicysteine target peptide tag that was genetically fused to a protein of interest. This method allows for the subsequent attachment of azide-functionalized cargo in the facile synthesis of novel protein-cargo conjugates. However, the fluorogenic aspect of the reaction between the linker and the target peptide was less than we desired. To address this shortcoming, a second linker reagent was prepared. This new design also allowed for the site-specific introduction of an alkyne functional group onto the target peptide, but in a highly fluorogenic and rapid manner. The site-specific addition of an alkyne group to a protein of interest was thus monitored in situ by fluorescence increase, prior to the attachment of azide-functionalized cargo. Finally, we also demonstrated that the cargo can also be attached first, in an azide/alkyne cycloaddition reaction, prior to fluorogenic conjugation with the target peptide-fused protein.

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25

Buscemi, Gabriella, Francesco Milano, Danilo Vona, Gianluca M. Farinola, and Massimo Trotta. "Effect of chemical substitution on the surface charge of the photosynthetic Reaction Center from Rhodobacter sphaeroides: an in-silico investigation." MRS Advances 5, no. 45 (2020): 2309–16. http://dx.doi.org/10.1557/adv.2020.281.

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The Reaction Centers (RCs) proteins are membrane proteins representing the key component so flight energy transduction in photosynthetic organisms. Upon photon absorption, these photoenzymes produce a long lasting intra protein hole electron couples whose charges are separated by 3 nanometers. The dipoles formed within the RCs can be effectively employed as transducing cores of several biological-organic hybrid devices whose design can accomplish photocurrents generation or act as phototransistor. To widen the application of the RCs to as many substrate as possible one valuable strategy is the bioconjugation of the protein with specific molecules ad-hoc selected to improve enzymatic performance and/or integration in proper scaffolding. In the present manuscript, we investigate the changes of the isoelectric point of the RC from the carotenoidless strain of the photosynthetic bacterium Rhodobacter sphaeroides R26 by inducing “in silico” mutations to predict on the role of the aminoacids involved in the bioconjugation.

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26

Vetriselvan, Moorthy, Manickam Pramesh, Selvaraj Jayanthi, Kittappa Gunasundari, and Ponnusamy Shanmugam. "One Pot Multicomponent Synthesis of Highly Commutated 1,2,3-Triazoles using some Pyrazole aldehyde through “Click” Reaction." Oriental Journal Of Chemistry 38, no. 2 (April 29, 2022): 295–301. http://dx.doi.org/10.13005/ojc/380209.

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1,2,3 Trizole compounds are widely applied in major several technical and research areas especially in drug discovery new chemical entities like trizoles are developed via click reactions. Synthesis of heterocycles through cycloaddition reaction between azides and alkynes by employing and azides using copper as catalyst is said to be Click reaction. Most commonly triazoles are utilized in medicinal field as a drug linkers for bioconjugation. It found to have potential multiple applications in biological as well as medical sciences. We describe herein the novel and efficient three step multicomponent synthesis of highly substituted 1,2,3-triazole derivatives from pyrazole aldehyde, diaminobenzene via N-alkylation by Click reaction.For the future, our perspective is studies of anti-cancer, anti-viral and antimicrobial activities in 1,2,3-triazole.

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27

Da Pieve, Chiara, Ata Makarem, Stephen Turnock, Justyna Maczynska, Graham Smith, and Gabriela Kramer-Marek. "Thiol-Reactive PODS-Bearing Bifunctional Chelators for the Development of EGFR-Targeting [18F]AlF-Affibody Conjugates." Molecules 25, no. 7 (March 29, 2020): 1562. http://dx.doi.org/10.3390/molecules25071562.

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Site-selective bioconjugation of cysteine-containing peptides and proteins is currently achieved via a maleimide–thiol reaction (Michael addition). When maleimide-functionalized chelators are used and the resulting bioconjugates are subsequently radiolabeled, instability has been observed both during radiosynthesis and post-injection in vivo, reducing radiochemical yield and negatively impacting performance. Recently, a phenyloxadiazolyl methylsulfone derivative (PODS) was proposed as an alternative to maleimide for the site-selective conjugation and radiolabeling of proteins, demonstrating improved in vitro stability and in vivo performance. Therefore, we have synthesized two novel PODS-bearing bifunctional chelators (NOTA-PODS and NODAGA-PODS) and attached them to the EGFR-targeting affibody molecule ZEGFR:03115. After radiolabeling with the aluminum fluoride complex ([18F]AlF), both conjugates showed good stability in murine serum. When injected in high EGFR-expressing tumor-bearing mice, [18F]AlF-NOTA-PODS-ZEGFR:03115 and [18F]AlF-NODAGA-PODS-ZEGFR:03115 showed similar pharmacokinetics and a specific tumor uptake of 14.1 ± 5.3% and 16.7 ± 4.5% ID/g at 1 h post-injection, respectively. The current results are encouraging for using PODS as an alternative to maleimide-based thiol-selective bioconjugation reactions.

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28

St. Amant, Andre H., Daniel Lemen, Stelios Florinas, Shenlan Mao, Christine Fazenbaker, Haihong Zhong, Herren Wu, Changshou Gao, R. James Christie, and Javier Read de Alaniz. "Tuning the Diels–Alder Reaction for Bioconjugation to Maleimide Drug-Linkers." Bioconjugate Chemistry 29, no. 7 (June 22, 2018): 2406–14. http://dx.doi.org/10.1021/acs.bioconjchem.8b00320.

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29

Hartley, Andrew M., Harley L. Worthy, Samuel C. Reddington, Pierre J. Rizkallah, and D. Dafydd Jones. "Molecular basis for functional switching of GFP by two disparate non-native post-translational modifications of a phenyl azide reaction handle." Chemical Science 7, no. 10 (2016): 6484–91. http://dx.doi.org/10.1039/c6sc00944a.

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Through the genetic incorporation of a single phenyl azide group into superfolder GFP (sfGFP) at residue 148 we provide a molecular description of how this highly versatile chemical handle can be used to positively switch protein function in vitro and in vivo via either photochemistry or bioconjugation.

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30

De Rosa, Lucia, Rossella Di Stasi, Alessandra Romanelli, and Luca Domenico D’Andrea. "Exploiting Protein N-Terminus for Site-Specific Bioconjugation." Molecules 26, no. 12 (June 9, 2021): 3521. http://dx.doi.org/10.3390/molecules26123521.

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Although a plethora of chemistries have been developed to selectively decorate protein molecules, novel strategies continue to be reported with the final aim of improving selectivity and mildness of the reaction conditions, preserve protein integrity, and fulfill all the increasing requirements of the modern applications of protein conjugates. The targeting of the protein N-terminal alpha-amine group appears a convenient solution to the issue, emerging as a useful and unique reactive site universally present in each protein molecule. Herein, we provide an updated overview of the methodologies developed until today to afford the selective modification of proteins through the targeting of the N-terminal alpha-amine. Chemical and enzymatic strategies enabling the selective labeling of the protein N-terminal alpha-amine group are described.

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31

Hiscocks, Hugh G., Alison T. Ung, and Giancarlo Pascali. "Novel Strategy for Non-Aqueous Bioconjugation of Substituted Phenyl-1,2,4-triazole-3,5-dione Analogues." Molecules 27, no. 19 (October 7, 2022): 6667. http://dx.doi.org/10.3390/molecules27196667.

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A novel 4-[4-(pentafluoro-λ⁶-sulfanyl)phenyl]-1,2,4-triazole-3,5-dione (5a) was synthesised as a potential [18F]radio-prosthetic group for radiolabelling peptides and proteins via selective bioconjugation with the phenolic side chains of tyrosine residues. Preliminary conjugation tests revealed the rapid hydrolysis of 5a under semi-aqueous conditions; these results led to further investigation into the electronic substituent effects of PTAD derivatives and corresponding hydrolytic stabilities. Five derivatives of 5a with para substituents of varying electron donating and withdrawing effects were synthesised for the investigation. The bioconjugation of these derivatives with model tyrosine was monitored in both aqueous and organic media in the presence of a variety of catalysts. From these investigations, we have found HFIP to be an effective catalyst when used in tandem with DCM as a solvent to give PTAD-tyrosine conjugate products (6a–f) in satisfactory to good yields (54–79%), whereas analogous reactions performed in acetonitrile were unsuccessful. The discovery of this system has allowed for the successful conjugation of electron-deficient PTAD derivatives to tyrosine, which would otherwise be unachievable under aqueous reaction conditions. The inclusion of these electron-deficient, fluorinated PTAD derivatives for use in the PTAD-tyrosine conjugation will hopefully broaden their applicability within fields such as 19F-MRI and PET imaging.

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Méndez, Yanira, Janoi Chang, Ana R. Humpierre, Abel Zanuy, Raine Garrido, Aldrin V. Vasco, Jessy Pedroso, et al. "Multicomponent polysaccharide–protein bioconjugation in the development of antibacterial glycoconjugate vaccine candidates." Chemical Science 9, no. 9 (2018): 2581–88. http://dx.doi.org/10.1039/c7sc05467j.

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33

Belviso, Benny Danilo, Rocco Roberto Tangorra, Francesco Milano, Omar Hassan Omar, Simona la Gatta, Roberta Ragni, Angela Agostiano, Gianluca M. Farinola, Rocco Caliandro, and Massimo Trotta. "Crystallographic analysis of the photosynthetic reaction center from Rhodobacter sphaeroides bioconjugated with an artificial antenna." MRS Advances 1, no. 57 (2016): 3789–800. http://dx.doi.org/10.1557/adv.2016.10.

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ABSTRACTA high-throughput crystallographic investigation on several crystals of photosynthetic reaction center covalently bound to an ad-hoc synthesized artificial antenna (AE600) is presented. The investigation did not show a preferential binding site of the antenna molecule AE600 to the reaction center in the solid phase. An accurate crystallographic study allowed identifying a lysine residue sitting on periplasmic side of the protein as one of the bioconjugation sites. The residue sits on subunit M of the protein, in close proximity to the bacteriochlorophylls of the reaction center involved in the light absorption and conversion processes. Distances obtained from the crystallographic structure confirm that energy transfer between the antenna and the protein proceed with the Förster resonance mechanism.

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34

Aflak, Noura, Hicham Ben El Ayouchia, Lahoucine Bahsis, Hafid Anane, Miguel Julve, and Salah-Eddine Stiriba. "Recent Advances in Copper-Based Solid Heterogeneous Catalysts for Azide–Alkyne Cycloaddition Reactions." International Journal of Molecular Sciences 23, no. 4 (February 21, 2022): 2383. http://dx.doi.org/10.3390/ijms23042383.

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The copper(I)-catalyzed azide−alkyne cycloaddition (CuAAC) reaction is considered to be the most representative ligation process within the context of the “click chemistry” concept. This CuAAC reaction, which yields compounds containing a 1,2,3-triazole core, has become relevant in the construction of biologically complex systems, bioconjugation strategies, and supramolecular and material sciences. Although many CuAAC reactions are performed under homogenous conditions, heterogenous copper-based catalytic systems are gaining exponential interest, relying on the easy removal, recovery, and reusability of catalytically copper species. The present review covers the most recently developed copper-containing heterogenous solid catalytic systems that use solid inorganic/organic hybrid supports, and which have been used in promoting CuAAC reactions. Due to the demand for 1,2,3-triazoles as non-classical bioisosteres and as framework-based drugs, the CuAAC reaction promoted by solid heterogenous catalysts has greatly improved the recovery and removal of copper species, usually by simple filtration. In so doing, the solving of the toxicity issue regarding copper particles in compounds of biological interest has been achieved. This protocol is also expected to produce a practical chemical process for accessing such compounds on an industrial scale.

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35

Folikumah, Makafui Y., Marc Behl, and Andreas Lendlein. "Reaction behaviour of peptide-based single thiol-thioesters exchange reaction substrate in the presence of externally added thiols." MRS Communications 11, no. 4 (July 14, 2021): 402–10. http://dx.doi.org/10.1557/s43579-021-00041-z.

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Abstract Identification of patterns in chemical reaction pathways aids in the effective design of molecules for specific applications. Here, we report on model reactions with a water-soluble single thiol-thioester exchange (TTE) reaction substrate, which was designed taking in view biological and medical applications. This substrate consists of the thio-depsipeptide, Ac-Pro-Leu-Gly-SLeu-Leu-Gly-NEtSH (TDP) and does not yield foul-smelling thiol exchange products when compared with aromatic thiol containing single TTE substrates. TDP generates an α,ω-dithiol crosslinker in situ in a ‘pseudo intramolecular’ TTE. Competitive intermolecular TTE of TDP with externally added “basic” thiols increased the crosslinker concentration whilst “acidic” thiols decreased its concentration. TDP could potentially enable in situ bioconjugation and crosslinking applications. Graphic abstract The competition between ‘pseudo intramolecular’ and intermolecular exchange of a peptide-based thiol-thioester exchange (TTE) substrate can be used to control the relative amount of final exchange products based on size and pKa values of externally added thiols. Potential application of this system can be seen in the development of TTE substrates for the rapid identification of thiols by dynamic combinatorial screening.

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36

Zhang, Yiru, Jianlei Shen, Rong Hu, Xiujuan Shi, Xianglong Hu, Benzhao He, Anjun Qin, and Ben Zhong Tang. "Fast surface immobilization of native proteins through catalyst-free amino-yne click bioconjugation." Chemical Science 11, no. 15 (2020): 3931–35. http://dx.doi.org/10.1039/d0sc00062k.

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37

Ban, Hitoshi, Masanobu Nagano, Julia Gavrilyuk, Wataru Hakamata, Tsubasa Inokuma, and Carlos F. Barbas. "Facile and Stabile Linkages through Tyrosine: Bioconjugation Strategies with the Tyrosine-Click Reaction." Bioconjugate Chemistry 24, no. 4 (March 27, 2013): 520–32. http://dx.doi.org/10.1021/bc300665t.

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38

Silvestri, Anthony P., Philip A. Cistrone, and Philip E. Dawson. "Adapting the Glaser Reaction for Bioconjugation: Robust Access to Structurally Simple, Rigid Linkers." Angewandte Chemie International Edition 56, no. 35 (July 21, 2017): 10438–42. http://dx.doi.org/10.1002/anie.201705065.

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39

Cui, Cheng, Hui Zhang, Ruowen Wang, Sena Cansiz, Xiaoshu Pan, Shuo Wan, Weijia Hou, et al. "Recognition-then-Reaction Enables Site-Selective Bioconjugation to Proteins on Live-Cell Surfaces." Angewandte Chemie International Edition 56, no. 39 (August 25, 2017): 11954–57. http://dx.doi.org/10.1002/anie.201706285.

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40

Silvestri, Anthony P., Philip A. Cistrone, and Philip E. Dawson. "Adapting the Glaser Reaction for Bioconjugation: Robust Access to Structurally Simple, Rigid Linkers." Angewandte Chemie 129, no. 35 (July 21, 2017): 10574–78. http://dx.doi.org/10.1002/ange.201705065.

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41

Cui, Cheng, Hui Zhang, Ruowen Wang, Sena Cansiz, Xiaoshu Pan, Shuo Wan, Weijia Hou, et al. "Recognition-then-Reaction Enables Site-Selective Bioconjugation to Proteins on Live-Cell Surfaces." Angewandte Chemie 129, no. 39 (August 25, 2017): 12116–19. http://dx.doi.org/10.1002/ange.201706285.

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42

Rahim, Maha K., Rajesh Kota, Sumi Lee, and Jered B. Haun. "Bioorthogonal chemistries for nanomaterial conjugation and targeting." Nanotechnology Reviews 2, no. 2 (April 1, 2013): 215–27. http://dx.doi.org/10.1515/ntrev-2012-0083.

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AbstractBioorthogonal chemistries are covalent reaction pairs that proceed in the presence of biological components with complete specificity. A suite of reactions has been described to date that provides scientists and engineers with diverse operational characteristics for different applications. Nanomaterials in particular have benefitted from these new capabilities, resulting in improved coupling efficiencies and multifunctionality. In this review, we will discuss the application of bioorthogonal chemistries to different nanomaterial systems, highlighting the advantages and limitations for use in bioconjugation. We will also describe how recent improvements in the reaction speed of catalyst-free bioorthogonal chemistries have enabled the successful coupling of nanomaterials directly to live cells. Using a recently developed reaction pair, tetrazine and trans-cyclooctene, the direct covalent coupling to cells has been shown to occur on time-scales that are relevant for biological studies and diagnostic applications and can even amplify nanomaterial binding greater than tenfold relative to traditional immunoconjugates. This powerful technique still maintains exquisite specificity, however, yielding robust results in clinical diagnostic applications using human tissue and blood samples. Future work will likely focus on further advancement of the in situ amplification technique, such as increasing nanomaterial binding, enabling multiplexed detection through the use of orthogonal reaction systems and extension to applications in vivo.

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43

Zhang, Song-Lin, and Jia-Jia Dong. "Mechanism and chemoselectivity origins of bioconjugation of cysteine with Au(iii)-aryl reagents." Organic & Biomolecular Chemistry 17, no. 5 (2019): 1245–53. http://dx.doi.org/10.1039/c8ob03143f.

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A detailed computational study is presented on the reaction mechanism of selective cysteine S-arylation by cationic Au(iii)-aryl reagents. The chemoselectivity origins have been elucidated through comparison with potential N- and O-arylation, showing that the acidity and nucleophilicity of the residue are two inherent controlling factors.

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44

Barbosa, Mariana, Cristina Martins, and Paula Gomes. ""Click" chemistry as a tool to create novel biomaterials: a short review." U.Porto Journal of Engineering 1, no. 1 (October 1, 2015): 22–34. http://dx.doi.org/10.24840/10.24840/2183-6493_001.001_0004.

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In recent years, there has been a growing demand for novel strategies for biomedical applications. Chitosan is a typical cationic amino-containing polysaccharide that has been widely used due to its unique properties. The grafting modification of chitosan has been explored as an interesting method to develop multifunctional novel chitosan hybrid materials for drug delivery, tissue engineering, and other biomedical applications. Recently, “click” chemistry has been introduced into the synthesis of polymeric materials with well-defined and complex chain architectures. The Huisgen’s 1,3-dipolar cycloaddition reaction between alkynes and azides yielding triazoles is the principal example of a “click” reaction. Bioconjugation, surface modification, and orthogonal functionalization of polymers were successfully performed through this chemoselective reaction. In recent literature interest has been shown in this cycloaddition for the modification of polysaccharides, however, only a few chitosan graft copolymers have been synthesized by this technique.

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45

Barbosa, Mariana, Cristina Martins, and Paula Gomes. ""Click" chemistry as a tool to create novel biomaterials: a short review." U.Porto Journal of Engineering 1, no. 1 (September 5, 2017): 22–34. http://dx.doi.org/10.24840/2183-6493_001.001_0004.

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Abstract:

In recent years, there has been a growing demand for novel strategies for biomedical applications. Chitosan is a typical cationic amino-containing polysaccharide that has been widely used due to its unique properties. The grafting modification of chitosan has been explored as an interesting method to develop multifunctional novel chitosan hybrid materials for drug delivery, tissue engineering, and other biomedical applications. Recently, “click” chemistry has been introduced into the synthesis of polymeric materials with well-defined and complex chain architectures. The Huisgen’s 1,3-dipolar cycloaddition reaction between alkynes and azides yielding triazoles is the principal example of a “click” reaction. Bioconjugation, surface modification, and orthogonal functionalization of polymers were successfully performed through this chemoselective reaction. In recent literature interest has been shown in this cycloaddition for the modification of polysaccharides, however, only a few chitosan graft copolymers have been synthesized by this technique.

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46

Witus, Leah S., and Matthew Francis. "Site-Specific Protein Bioconjugation via a Pyridoxal 5′-Phosphate-Mediated N-Terminal Transamination Reaction." Current Protocols in Chemical Biology 2, no. 2 (April 2010): 125–34. http://dx.doi.org/10.1002/9780470559277.ch100018.

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47

Tolnai, Gergely L., Jonathan P. Brand, and Jerome Waser. "Gold-catalyzed direct alkynylation of tryptophan in peptides using TIPS-EBX." Beilstein Journal of Organic Chemistry 12 (April 19, 2016): 745–49. http://dx.doi.org/10.3762/bjoc.12.74.

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The selective functionalization of peptides containing only natural amino acids is important for the modification of biomolecules. In particular, the installation of an alkyne as a useful handle for bioconjugation is highly attractive, but the use of a carbon linker is usually required. Herein, we report the gold-catalyzed direct alkynylation of tryptophan in peptides using the hypervalent iodine reagent TIPS-EBX (1-[(triisopropylsilyl)ethynyl]-1,2-benziodoxol-3(1H)-one). The reaction proceeded in 50–78% yield under mild conditions and could be applied to peptides containing other nucleophilic and aromatic amino acids, such as serine, phenylalanine or tyrosine.

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Meguro, Tomohiro, Norikazu Terashima, Harumi Ito, Yuka Koike, Isao Kii, Suguru Yoshida, and Takamitsu Hosoya. "Staudinger reaction using 2,6-dichlorophenyl azide derivatives for robust aza-ylide formation applicable to bioconjugation in living cells." Chemical Communications 54, no. 57 (2018): 7904–7. http://dx.doi.org/10.1039/c8cc00179k.

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Efficient formation of water- and air-stable aza-ylides has been achieved by the Staudinger reaction. The reaction proceeds rapidly and has been successfully applied to chemical modification of proteins in living cells.

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Zhang, Hang, Jinlong Chen, Chunsheng Xiao, Youhua Tao, and Xianhong Wang. "A Multifunctional Polypeptide via Ugi Reaction for Compact and Biocompatible Quantum Dots with Efficient Bioconjugation." Bioconjugate Chemistry 29, no. 4 (March 5, 2018): 1335–43. http://dx.doi.org/10.1021/acs.bioconjchem.8b00072.

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Young, Aidan G., A. James McQuillan, and David P. Green. "In Situ IR Spectroscopic Studies of the Avidin−Biotin Bioconjugation Reaction on CdS Particle Films." Langmuir 25, no. 13 (July 7, 2009): 7416–23. http://dx.doi.org/10.1021/la900350s.

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