Die Entwicklung der Thiol‐En‐Kupplung als Klick‐Prozess für die Materialwissenschaften und die bioorganische Chemie

Dondoni, Alessandro

doi:10.1002/ange.200802516

Cited by 88 publications

(26 citation statements)

References 42 publications

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“…[41] Recently, it has attracted great interest as a click reaction, since it does not require a metal catalyst, proceeds under very mild conditions, and is insensitive to water and oxygen. [42] The ready availa-bility of thiol-functional biomolecules is an additional advantage. Several excellent reviews exemplify the many applications of the versatile thiol-ene reaction [40c, 41b, 42b, 43] Examples of successful application are the modification of surfaces, [44] polymers, [45] and the preparation of dendrimeric structures [46] and soft polymeric stamps; [47] this reaction was even demonstrated to proceed in sunlight without extra irradiation with UV light.…”

Section: Introductionmentioning

confidence: 99%

Biofunctional Silicon Nanoparticles by Means of Thiol‐Ene Click Chemistry

Ruizendaal

Pujari

Gevaerts

et al. 2011

Chemistry An Asian Journal

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The preparation and characterization of butylene‐terminated silicon nanoparticles (SiNPs) and their functionalization using thiol‐ene chemistry is described, as well as the coupling of DNA strands. Bromide‐terminated SiNPs were prepared by means of the oxidation of magnesium silicide and functionalized with butylene chains through treatment with the corresponding Grignard reagent. The successful coupling was confirmed by NMR and FTIR spectroscopy. TEM measurements revealed a silicon‐core diameter of (2.4±0.5) nm. The fluorescence emission maximum is at λmax=525 nm when excited at λexc=430 nm. The conjugation of these alkene‐terminated SiNPs by means of thiol‐ene chemistry is described for a variety of functional thiols. Efficient coupling was evidenced by NMR and FTIR spectroscopy. Moreover, the characteristic fluorescence properties of the SiNPs remained unaltered, thus demonstrating the value of this approach towards functional oxide‐free SiNPs. Activation of the attached carboxylic acid moieties allowed for conjugation of NH2‐terminated oligo‐ssDNA (ss=single strand) to the SiNPs. Successful coupling was confirmed by a characteristic new UV absorption band at 260 nm, and by the still‐present distinctive fluorescence of the SiNPs at 525 nm. Gel electrophoresis confirmed coupling of 2 to 3 DNA strands onto the SiNPs, whereas no uncoupled DNA was observed.

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Section: Introductionmentioning

confidence: 99%

Biofunctional Silicon Nanoparticles by Means of Thiol‐Ene Click Chemistry

Ruizendaal

Pujari

Gevaerts

et al. 2011

Chemistry An Asian Journal

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“…Therefore, the thiol-ene reaction has started to attract researchers in various areas of material synthesis. [7][8][9][10][11][12][13] In our laboratories, the copper-catalyzed Huisgen 1,3-dipolar azide/ alkyne cycloaddition process [14][15][16][17][18] as well as the equally effective hetero Diels-Alder conjugation chemistries [19][20][21] have been used successfully for a number of efficient coupling reactions.…”

Section: Introductionmentioning

confidence: 99%

Surface Modification of Poly(divinylbenzene) Microspheres via Thiol−Ene Chemistry and Alkyne−Azide Click Reactions

et al. 2009

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We report the functionalization of cross-linked poly(divinylbenzene) (pDVB) microspheres using both thiol-ene chemistry and azide-alkyne click reactions. The RAFT technique was carried out to synthesize SH-functionalized poly(N-isopropylacrylamide) (pNIPAAm) and utilized to generate pNIPAAm surface-modified microspheres via thiol-ene modification. The accessible double bonds on the surface of the microspheres allow the direct coupling with thiol-end functionalized pNIPAAm. In a second approach, pDVB microspheres were grafted with poly(2-hydroxyethyl methacrylate) (pHEMA). For this purpose, the residual double bonds on the microspheres surface were used to attach azide groups via the thiol-ene approach of 1-azido-undecane-11-thiol. In a second step, alkyne endfunctionalized pHEMA was used to graft pHEMA to the azide-modified surface via click-chemistry (Huisgen 1,3-dipolar cycloaddition). The surface-sensitive characterization methods X-ray photoelectron spectroscopy, scanning-electron microscopy and FT-IR transmission spectroscopy were employed to characterize the successful surface modification of the microspheres. In addition, fluorescence microscopy confirms the presence of grafted pHEMA chains after labeling with Rhodamine B.

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“…[14] The great potential of this high yielding reaction that is not metal-based catalyst dependent and is compatible with oxygen and water has been amply documented in polymer chemistry and to a lesser extent in bioorganic chemistry. [15] The potential role of this reaction in carbohydrate and protein chemistry has been validated, however, by significant applications such as heteroglycoclusters, [16] vaccines, [17] and S-disaccharides [18] syntheses as well as by the site-specific immobilization and patterning of proteins. [19] We considered the study of the hydrothiolation of allyl Cglycosides by an SH-free cysteine derivative propaedeutic to our ultimate goal consisting of peptide and protein glycosylation.…”

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confidence: 99%