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6 article(s) from Ravoo, Bart Jan

A dynamic combinatorial library for biomimetic recognition of dipeptides in water

Florian Klepel and
Bart Jan Ravoo

Beilstein J. Org. Chem. 2020, 16, 1588–1595, doi:10.3762/bjoc.16.131

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Scheme 1: a) Building blocks included in this study. b) Antiparallel and parallel constitutional isomers of t...

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Figure 1: HPLC–MS chromatograms of a reference library for all possible tripeptide dimers ([M + H]⁺ ions).

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Figure 2: a) HPLC–MS chromatograms of the dimers (CFC)₂ and templates YY and FF. b) Amplification of the peak...

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Scheme 2: a) Synthesis of the parallel and antiparallel isomers p(CFC)₂ and a(CFC)₂_. b) Templates FF. YY and ...

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Figure 3: ITC of YY (30 mM) to a(CFC)₂ (1.5 mM) in phosphate buffer (pH 7.4, 100 mM).

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Figure 4: Continuously varied NMR measurements of a) p(CFC)₂ to YY b) p(CFC)₂ to FF c) a(CFC)₂ to YY d) a(CFC)...

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Figure 5: Job plots derived from the continuously varied NMR measurements of a) p(CFC)₂ to YY b) p(CFC)₂ to FF...

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Published 02 Jul 2020

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Reversible end-to-end assembly of selectively functionalized gold nanorods by light-responsive arylazopyrazole–cyclodextrin interaction

Maximilian Niehues,
Patricia Tegeder and
Bart Jan Ravoo

Beilstein J. Org. Chem. 2019, 15, 1407–1415, doi:10.3762/bjoc.15.140

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Scheme 1: Light-responsive end-to-end assembly of host-functionalized gold nanorods (AuNR) by cyclodextrin–AA...

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Scheme 2: Two-step ligand exchange reaction for the synthesis of water-soluble cyclodextrin end-functionalize...

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Figure 1: a) ζ-Potential measurement of different stages of the ligand exchange. b) UV–vis spectroscopy befor...

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Figure 2: UV–vis spectroscopy of a) [tCD+tTEG]AuNR with different amount of dAAP (0-35 µM). b) [tCD]AuNR with...

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Figure 3: SPR maxima of [tCD+tTEG]AuNR with dAAP during four cycles of irradiation. a) Longitudinal SPR. b) T...

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Figure 4: TEM-BF images of a) [tCD+tTEG]AuNR. b and c) AuNR end-to-end assemblies by dAAP (15 µM). d) Dissolv...

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Figure 5: Reversible aggregation of [tCD+tTEG]AuNR by addition of dAAP (15 µM) monitored by dynamic light sca...

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Published 26 Jun 2019

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A self-assembled cyclodextrin nanocarrier for photoreactive squaraine

Ulrike Kauscher and
Bart Jan Ravoo

Beilstein J. Org. Chem. 2016, 12, 2535–2542, doi:10.3762/bjoc.12.248

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Figure 1: Schematic representation of adamantane-substituted squaraine (AdSq) binding as a divalent guest to ...

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Figure 2: Absorption spectra of AdSq in acetonitrile. [AdSq] = 7.5 µM. Top: Absorption at different time poin...

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Figure 3: Top: Emission spectra (ex: 630 nm) of AdSq immobilized at CDV. [CDV] = 0–100 µM; [AdSq] = 5 µM. Bot...

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Figure 4: Confocal fluorescence microscopy of giant unilamellar vesicles (GUVs) of amphiphilic cyclodextrins ...

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Figure 5: Top: Absorption spectra at different time points during irradiation of a CDV solution with AdSq imm...

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Figure 6: Synthesis of AdSq (I) NaH, DMF, 1,6-dibromohexane, 24 h, rt. (II) benzothiazole, acetonitrile, 12 h...

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Published 25 Nov 2016

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Towards the sequence-specific multivalent molecular recognition of cyclodextrin oligomers

Michael Kurlemann and
Bart Jan Ravoo

Beilstein J. Org. Chem. 2014, 10, 2428–2440, doi:10.3762/bjoc.10.253

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Figure 1: Chemical structures of the di- (A) and trivalent (B) CD sequences, the di- (C) and trivalent (D) gu...

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Figure 2: Synthesis of the di- and trivalent CD sequences 1–7 (for detailed reaction conditions see Supporting Information File 1).

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Figure 3: Solid phase peptide synthesis of the di- and trivalent guest strands 8 – 14 (for detailed reaction ...

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Figure 4: ¹H NMR spectra of 17 (B) and its inclusion complexes with β- (A) and α-CD (C), measured in D₂O (600...

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Figure 5: Schematic drawing of the complexation of the serine derivatives 17 (A) and 18 (B) with α- and β-CD....

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Figure 6: ¹H NMR spectra of 18 (B) and its inclusion complexes with β- (A) and α-CD (C), measured in D₂O (600...

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Figure 7: Selected binding models for the analysis of ITC data. (A) Monovalent receptor (R)-ligand (L) intera...

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Figure 8: Schematic drawing of the interactions of the divalent guest molecules 8 (A), 9 (B) and 10 (C) with ...

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Figure 9: Schematic drawing of the interactions of the trivalent guest molecules 11 (A), 12 (B), 13 (C) and 14...

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Published 20 Oct 2014

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Molecular recognition of surface-immobilized carbohydrates by a synthetic lectin

Melanie Rauschenberg,
Eva-Corrina Fritz,
Christian Schulz,
Tobias Kaufmann and
Bart Jan Ravoo

Beilstein J. Org. Chem. 2014, 10, 1354–1364, doi:10.3762/bjoc.10.138

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Figure 1: Molecular structures of carbohydrates (NANA, Glc, Gal, Man) immobilized on epoxide SAMs, NANA-bindi...

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Figure 2: Schematic representation of the preparation of a simple carbohydrate microarray by μCP of amine-fun...

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Figure 3: Optical microscopy images of water droplets selectively condensed in the areas where (A) the NANA i...

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Figure 4: (A) AFM height image (zoom) of NANA ink in 10 μm stripes on an epoxide-terminated SAM; (B) Height p...

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Figure 5: Fluorescence images of bifunctional carbohydrate microarrays incubated with FITC-HisHis. (A) NANA (...

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Figure 6: Overlay of fluorescence images of bifunctional carbohydrate microarrays; (A) NANA (dots 10 × 5 μm) ...

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Figure 7: Fluorescence images of a microarray consisting of NANA (dots 5 × 3 μm) and Man (background). (A) In...

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Figure 8: Fluorescence images of a microarray of NANA (dots 5 × 3 μm) and Glc (background), first incubated w...

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Published 16 Jun 2014

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Mannose-decorated cyclodextrin vesicles: The interplay of multivalency and surface density in lectin–carbohydrate recognition

Ulrike Kauscher and
Bart Jan Ravoo

Beilstein J. Org. Chem. 2012, 8, 1543–1551, doi:10.3762/bjoc.8.175

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Figure 1: Mannose–adamantane conjugates 1–4 and amphiphilic cyclodextrin 5.

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Figure 2: Integrated peak area (left) and raw titration curves (right) for the ITC measurements of 1–4 with β...

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Figure 3: Schematic presentation of the binding between β-cyclodextrin and (A) monovalent guest 1, (B) divale...

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Figure 4: (A) Agglutination of β-cyclodextrin vesicles in the presence of monovalent guest 1 and ConA. The su...

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Figure 5: (A) Agglutination dependence of β-cyclodextrin vesicles in the presence of guests 2–4. Legend: red ...

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Figure 6: (A) Agglutination of β-cyclodextrin vesicles in the presence of guest 2 or 3 and ConA. Legend: red ...

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Figure 7: Schematic presentation of the binding of (A) a monovalent, (B) a divalent, or (C) a trivalent guest...

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Figure 8: (A) Agglutination of β-cyclodextrin vesicles in the presence of guest 2 or 4 and ConA. Legend: red ...

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Figure 9: Schematic presentation of the binding of guest molecules with (A) one or (B) two mannose functions ...

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Published 17 Sep 2012

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