CuAAC: An Efficient Click Chemistry Reaction on Solid Phase

Castro, Vida; Rodríguez, Hortensia; Alberício, Fernando

doi:10.1021/acscombsci.5b00087

Cited by 196 publications

(162 citation statements)

References 170 publications

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“…The unnatural azido residue can be modified via click chemistry while immobilized on the solid support. 44 We used N-methyl propargylamine ( NMPA ) to click on a secondary amine. If the Fmoc protecting group is needed in future solution-phase modification, deprotection by the basic amine was avoided by doing repetitions of the click reaction.…”

Section: Resultsmentioning

confidence: 99%

An efficient methodology to introduce o-(aminomethyl)phenyl-boronic acids into peptides: alkylation of secondary amines

et al. 2017

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Current approaches for incorporating boronic acids into peptides require one of the following: the synthesis of commercially unavailable pinacol-protected boronate ester amino acid building blocks, amidation of small-molecule amine-containing boronic acids, or reductive amination of amine residues with 2-formylphenyl boronic acid. These methods have drawbacks, such as the use of excess starting materials, the lack of reactive-site specificity, or the inability to add multiple boronic acids in solution. In addition, several of these approaches do not allow for incorporation of the critical o-aminomethyl functionality that allows for binding of sacharrides under physiological conditions. In this work, we report three methods to functionalize synthetic peptides with boronic acids using solid-phase and solution-phase chemistries by alkylating a secondary amine with o-(bromomethyl)phenylboronic acid. Solution-phase chemistries afforded the highest yields, and were used to synthesize seven complex biotinylated multi-boronic acid peptides.

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Section: Resultsmentioning

confidence: 99%

An efficient methodology to introduce o-(aminomethyl)phenyl-boronic acids into peptides: alkylation of secondary amines

et al. 2017

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“…In contrast, the CuAAC can be used for ligation on the solid phase. 43 The two forms of the azide-alkyne click reaction, CuAAC and SPAAC, are therefore complementary and the respective advantages and disadvantages should be evaluated for each application.…”

Section: Resultsmentioning

confidence: 99%

Arginine side-chain modification that occurs during copper-catalysed azide–alkyne click reactions resembles an advanced glycation end product

et al. 2016

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“…[35][36][37][38] Employing again transparent TiO 2 electrodes, the focus moved to azide-decorated dyes with the intention to detect the surface functionalization optically. As modular and widely accepted mild functionalization reaction with terminal alkynes, the copper(I)-catalyzed 1,3-dipolar Huisgen cycloaddition reaction between an azide and an alkyne group, abbreviated as azide-alkyne "click" chemistry (AACC) in the following, was the first choice.…”

Section: Figurementioning

confidence: 99%

“…AACC experienced recently a tremendous development as an efficient, selective, but also mild and functional-group-tolerant coupling chemistry. [37,38] While electrochemically addressable protection groups are known for a variety of functional groups, [39][40][41][42][43][44][45] there are no suitable masking groups for alkynes reported so far to the best of our knowledge. [37,38] While electrochemically addressable protection groups are known for a variety of functional groups, [39][40][41][42][43][44][45] there are no suitable masking groups for alkynes reported so far to the best of our knowledge.…”

Section: Introductionmentioning

confidence: 99%

Electrochemical Multiplexing: Control over Surface Functionalization by Combining a Redox‐Sensitive Alkyne Protection Group with “Click”‐Chemistry

Hellstern

Gantenbein

Puebla‐Hellmann

et al. 2019

Adv Materials Inter

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and molecular electronics, [11,12] over medical diagnostic devices [13][14][15] to applications tuning macroscopic and/or environmental features like, e.g., the wettability [16][17][18] or the biocompatibility [19][20][21] of material surfaces. In most cases, a bifunctional molecule, combining an anchor group attaching the molecular compound to the surface with an exposed subunit representing the active moiety with tailored physiochemical properties is used to tune the surface's terminal appearance. While such approaches are successfully applied for entire objects and surfaces of considerable dimensions and macroscopic separations, there are limitations as soon as spatial patterns of varying surface functionalities and microscopic separations are desired or a spatially constrained surface-access including buried microfluidic chips has to be overcome. For example, conventional wet chemical surface functionalization procedures are spatially limited to the size of the droplet deposited (and its subsequent surface interaction) and methods depositing the molecules from gas-phase in vacuum require advanced masking strategies. Challenging are devices with a variety of molecular features to be created in a parallel process and in a locally controlled manner, like, e.g., multidimensional sensing platforms where a multitude of nearby molecular receptors are screening analytes in parallel. Or microfluidic chips with constrained access to functional sites as the channels are locally enclosed and inaccessible for droplet deposition. Of great interest are devices analyzing molecular binding events electronically, due to their miniaturization potential and the analyte-selective binding without the requirement of labels. In such devices, each electrode is electrically addressable in a separated manner as they were contacted individually. Such a preexisting electrical wiring scheme is a unique feature for an immobilization strategy able to distinguish between the applied electrical potentials of each electrode and a common electrolyte. The electrochemical release of thiol-based self-assembled monolayers (SAMs) on gold electrodes has been reported. [22] This allows the disintegration of existing SAMs. The subsequent decoration of the liberated electrode with an alternative thiol-molecule, however, is handicapped by scrambling with the remaining SAMs. Electrochemical triggered constructive build-up of molecular Local functionalization of surfaces is a current technological challenge. An electrochemically addressable alkyne protection group is presented enabling the site-selective liberation of alkynes exclusively on electrified electrodes. This controlled deprotection is based on a mendione chromophore which becomes a strong enough nucleophile upon reduction to intramolecularly attack the trialkylsilane alkyne protection group. The site-selective liberation of the alkyne is demonstrated by immobilizing the protected alkyne precursor on a transparent TiO 2 electrode and subsequently immobilizing red and blue azide dyes by azide-alky...

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CuAAC: An Efficient Click Chemistry Reaction on Solid Phase

Cited by 196 publications

References 170 publications

An efficient methodology to introduce o-(aminomethyl)phenyl-boronic acids into peptides: alkylation of secondary amines

An efficient methodology to introduce o-(aminomethyl)phenyl-boronic acids into peptides: alkylation of secondary amines

Arginine side-chain modification that occurs during copper-catalysed azide–alkyne click reactions resembles an advanced glycation end product

Electrochemical Multiplexing: Control over Surface Functionalization by Combining a Redox‐Sensitive Alkyne Protection Group with “Click”‐Chemistry

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