Rapid and Complete Surface Modification with Strain‐Promoted Oxidation‐Controlled Cyclooctyne‐1,2‐Quinone Cycloaddition (SPOCQ)

There is no author summary for this article yet. Authors can add summaries to their articles on ScienceOpen to make them more accessible to a non-specialist audience.

Abstract

Strain‐promoted oxidation‐controlled cyclooctyne‐1,2‐quinone cycloaddition (SPOCQ) between functionalized bicyclo[6.1.0]non‐4‐yne (BCN) and surface‐bound quinones revealed an unprecedented 100 % conjugation efficiency. In addition, monitoring by direct analysis in real time mass spectrometry (DART‐MS) revealed the underlying kinetics and activation parameters of this immobilization process in dependence on its microenvironment.

Related collections

Most cited references 34

Record: found
Abstract: found
Article: not found

In vivo imaging of membrane-associated glycans in developing zebrafish.

Scott Laughlin, Jeremy Baskin, Sharon Amacher … (2008)

Glycans are attractive targets for molecular imaging but have been inaccessible because of their incompatibility with genetically encoded reporters. We demonstrated the noninvasive imaging of glycans in live developing zebrafish, using a chemical reporter strategy. Zebrafish embryos were treated with an unnatural sugar to metabolically label their cell-surface glycans with azides. Subsequently, the embryos were reacted with fluorophore conjugates by means of copper-free click chemistry, enabling the visualization of glycans in vivo at subcellular resolution during development. At 60 hours after fertilization, we observed an increase in de novo glycan biosynthesis in the jaw region, pectoral fins, and olfactory organs. Using a multicolor detection strategy, we performed a spatiotemporal analysis of glycan expression and trafficking and identified patterns that would be undetectable with conventional molecular imaging approaches.

0 comments Cited 208 times – based on 0 reviews      Review now

Bookmark

Record: found
Abstract: found
Article: not found

Characterization of polydopamine thin films deposited at short times by autoxidation of dopamine.

Rebecca A Zangmeister, Todd Morris, Michael Tarlov (2013)

Current interest in melanin films derived from the autoxidation of dopamine stems from their use as a universal adhesion layer. Here we report chemical and physical characterization of polydopamine films deposited on gold surfaces from stirred basic solutions at times ranging from 2 to 60 min, with a focus on times ≤10 min. Data from Fourier transform infrared (FTIR), X-ray photoelectron spectroscopy (XPS), and electrochemical methods suggest the presence of starting (dopamine) and intermediate (C=N-containing tautomers of quinone and indole) species in the polydopamine films at all deposition times. A uniform overlayer analysis of the XPS data indicates that film thickness increased linearly at short deposition times of ≤10 min. At deposition times ≥10 min, the films appeared largely continuous with surface roughness ≈ ≤ 2 nm, as determined by atomic force microscopy (AFM). Pinhole-free films, as determined by anionic redox probe measurements, required deposition times of 60 min or greater.

0 comments Cited 162 times – based on 0 reviews      Review now

Bookmark

Record: found
Abstract: found
Article: not found

Mixed azide-terminated monolayers: a platform for modifying electrode surfaces.

James P. Collman, Neal Devaraj, Todd Eberspacher … (2006)

We have prepared and characterized mixed self-assembled monolayers (SAM) on gold electrodes from azido alkane thiols and various omega-functionalized alkane thiols. In the presence of copper(I) catalysts, these azide-modified surfaces are shown to react rapidly and quantitatively with terminal acetylenes forming 1,2,3-triazoles, via "click" chemistry. The initial azide substituents can be identified and monitored using both grazing-angle infrared (IR) and X-ray photoelectron spectrosopies. Acetylenes possessing redox-active ferrocene substituents react with the azide-terminated mixed SAMs and electrochemical measurements of the ferrocene-modified SAM electrodes have been used to quantify the redox centers attached to these platforms. Time-resolved electrochemical measurements have enabled us to follow the formation of these ferrocene centers and thus to measure the rate of the surface "click" reaction. Under optimal conditions this well-behaved second-order reaction takes place with a rate constant of 1 x 10(3) M(-)(1) s(-)(1). Typical reaction times of several minutes were realized using micromolar concentrations of acetylene. These techniques have been used to construct well-characterized, covalently modified monolayers that can be employed as functional electrode surfaces.

0 comments Cited 43 times – based on 0 reviews      Review now

Bookmark

All references

Author and article information

Contributors

Prof. Dr. Han Zuilhof:

ORCID: http://orcid.org/0000-0001-5773-8506

han.zuilhof@wur.nl

Journal

Journal ID (nlm-ta): Angew Chem Int Ed Engl

Journal ID (iso-abbrev): Angew. Chem. Int. Ed. Engl

Journal ID (doi): 10.1002/(ISSN)1521-3773

Journal ID (publisher-id): ANIE

Title: Angewandte Chemie (International Ed. in English)

Publisher: John Wiley and Sons Inc. (Hoboken )

ISSN (Print): 1433-7851

ISSN (Electronic): 1521-3773

Publication date (Electronic): 15 February 2017

Publication date (Print): 13 March 2017

Volume: 56

Issue: 12 ( doiID: 10.1002/anie.v56.12 )

Pages: 3299-3303

Affiliations

[ ¹ ] Laboratory of Organic ChemistryWageningen University and Research Stippeneng 4 6708 WE WageningenThe Netherlands

[ ² ] Department of Chemical and Materials EngineeringKing Abdulaziz University JeddahSaudi Arabia

Author notes

[†]

These authors contributed equally to this work.

Author information

Prof. Dr. Han Zuilhof http://orcid.org/0000-0001-5773-8506

Article

Publisher ID: ANIE201612037

DOI: 10.1002/anie.201612037

PMC ID: 5363232

PubMed ID: 28198134

SO-VID: 5fc3f811-790e-4944-aad4-6f50a58b5743

License:

This is an open access article under the terms of the Creative Commons Attribution‐NonCommercial‐NoDerivs License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non‐commercial and no modifications or adaptations are made.

History

Date received : 10 December 2016

Page count

Figures: 6, Tables: 2, References: 45, Pages: 5, Words: 0

Custom metadata

source-schema-version-number 2.0

component-id anie201612037

cover-date March 13, 2017

details-of-publishers-convertor Converter:WILEY_ML3GV2_TO_NLMPMC version:5.0.9 mode:remove_FC converted:23.03.2017

ScienceOpen disciplines: Chemistry

Keywords: cyclooctynes,kinetics,mass spectrometry,metal-free click chemistry,surface chemistry

Data availability:

ScienceOpen disciplines: Chemistry

Keywords: cyclooctynes, kinetics, mass spectrometry, metal-free click chemistry, surface chemistry

Rapid and Complete Surface Modification with Strain‐Promoted Oxidation‐Controlled Cyclooctyne‐1,2‐Quinone Cycloaddition (SPOCQ)

Read this article at

Abstract

Related collections

EPA CompTox Chemicals Dashboard

Most cited references 34

In vivo imaging of membrane-associated glycans in developing zebrafish.

Characterization of polydopamine thin films deposited at short times by autoxidation of dopamine.

Mixed azide-terminated monolayers: a platform for modifying electrode surfaces.

Author and article information

Contributors

Journal

Affiliations

Author notes

Author information

Article

History

Page count

Categories

Custom metadata

Comments

Comment on this article

Similar content 101

Cited by 7

Most referenced authors 1,032