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6 article(s) from Malanga, Milo

Homo- and hetero-difunctionalized β-cyclodextrins: Short direct synthesis in gram scale and analysis of regiochemistry

Gábor Benkovics,
Mihály Bálint,
Éva Fenyvesi,
Erzsébet Varga,
Szabolcs Béni,
Konstantina Yannakopoulou and
Milo Malanga

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Published 18 Mar 2019

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1. Graphical Abstract
2. Figure 1: Schematic representation of β-CD with glucopyranose atom numbering and with alphabetic labeling of ...
  
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3. Scheme 1: Syntheses of 6^A,6^X-diazido-β-CDs as reference compounds using the “capping” literature method [11,12].
  
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4. Scheme 2: Syntheses of homo-difunctionalized β-CDs using different reaction conditions.
  
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5. Figure 2: HPLC chromatograms of the authentic 6^A,6^X-diazido-β-CDs with known regiochemistry (references 1–3, Scheme 1...
  
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6. Figure 3: NMR spectral regions of the three ditosyl regioisomers in D₂O (500 MHz). The signals of the tosylat...
  
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7. Scheme 3: Syntheses of 6^A-monoazido-6^X-monotosyl-β-CDs using starting materials obtained from different react...
  
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8. Figure 4: Reversed-phase HPLC chromatograms of 6^A-monoazido-6^X-monotosyl-β-CDs prepared through reactions 4–8....
  
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9. Figure 5: HPLC separation of regioisomers and pseudoenantiomers of 6^A-monoazido-6^X-monotosyl-β-CD prepared in...
  
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10. Figure 6: Reversed-phase HPLC chromatograms of 6^A_,6^X-diazido-β-CDs prepared in reactions 9–13.
  
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Beilstein J. Org. Chem. 2019, 15, 710–720, doi:10.3762/bjoc.15.66

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Enhanced single-isomer separation and pseudoenantiomer resolution of new primary rim heterobifunctionalized α-cyclodextrin derivatives

Iveta Tichá,
Gábor Benkovics,
Milo Malanga and
Jindřich Jindřich

Full Research Paper
Published 13 Nov 2018

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1. Graphical Abstract
2. Figure 1: Schematic representation of native α-CD (1) and top view of its primary rim with alphabetic clockwi...
  
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3. Scheme 1: Synthesis of 6^A,6^X-diazido-α-CD derivatives 4 via 6^A,6^X-capped α-CDs 2 and 3 and their regioisomeri...
  
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4. Scheme 2: Synthesis of 6^A,6^X- and 6^A,6^D-diazido-α-CDs via 6^A,6^X-dibromo-α-CD 5, 6^A,6^D-dibromo-α-CD 5d interme...
  
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5. Scheme 3: Synthesis of 6^A,6^X-diazido-α-CDs via 6^A,6^X-ditosyl-α-CD intermediates 6 and their regioisomeric rat...
  
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6. Figure 2: HPLC chromatograms of 6^A,6^X-diazido-α-CDs 4 of the reactions 1–5, with ACN/water gradient elution a...
  
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7. Scheme 4: Synthesis of 6^A-azido-6^X-mesitylenesulfonyl-α-CD 8 and conversion into 6^A,6^X-diazido-α-CD 4.
  
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8. Figure 3: HPLC chromatograms of reaction 7 with separated 6^A-azido-α-CD 7 as starting material and regioisome...
  
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9. Figure 4: HPLC chromatograms of 6^A-azido-6^X-mesitylenesulfonyl-α-CD 8 (reaction 6): a) analytical and b) prep...
  
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10. Figure 5: ¹H NMR spectrum of the AC regioisomer 8c as a mixture of pseudoenantiomers prepared through reactio...
  
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11. Figure 6: ¹³C NMR spectrum of the AC regioisomer 8c as a mixture of pseudoenantiomers prepared through reacti...
  
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12. Figure 7: HPLC–MS chromatogram with the separated pseudoenantiomers of 6^A-azido-6^B-mesitylenesulfonyl-α-CD 8b...
  
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Beilstein J. Org. Chem. 2018, 14, 2829–2837, doi:10.3762/bjoc.14.261

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Novel β-cyclodextrin–eosin conjugates

Gábor Benkovics,
Damien Afonso,
András Darcsi,
Szabolcs Béni,
Sabrina Conoci,
Éva Fenyvesi,
Lajos Szente,
Milo Malanga and
Salvatore Sortino

Full Research Paper
Published 15 Mar 2017

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1. Graphical Abstract
2. Figure 1: Reaction scheme for the synthesis of eosin Y (2) and eosin B (4).
  
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3. Figure 2: Reaction scheme for the synthesis of eosin-appended β-CDs, 2–β-CD and 4–β-CD (NMM: N-methylmorpholi...
  
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4. Figure 3: TLC analysis of the composition of the crude coupling reaction mixtures.
  
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5. Figure 4: ¹H NMR spectrum of 2–β-CD with partial assignment (DMSO-d₆, 600 MHz, 298 K).
  
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6. Figure 5: Size distributions of 1 mM aqueous solutions of conjugates 4–β-CD (a) and 2–β-CD (b) at 25.0 °C (pH...
  
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7. Figure 6: Normalized absorption spectra of aqueous solutions of (a) eosin Y (2) and (b) conjugate 2–β-CD and ...
  
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8. Figure 7: Time-resolved fluorescence observed for aqueous solutions of (a) eosin Y (2) and (b) the 2–β-CD con...
  
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9. Figure 8: ¹O₂ luminescence detected upon 528 nm light excitation of D₂O solutions of (a) eosin Y (2) and (b) 2...
  
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Beilstein J. Org. Chem. 2017, 13, 543–551, doi:10.3762/bjoc.13.52

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New synthetic strategies for xanthene-dye-appended cyclodextrins

Milo Malanga,
Andras Darcsi,
Mihaly Balint,
Gabor Benkovics,
Tamas Sohajda and
Szabolcs Beni

Full Research Paper
Published 17 Mar 2016

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1. Graphical Abstract
2. Figure 1: Structures of fluorescent xanthene dyes. Rhodamine B·HCl 1 and fluorescein disodium salt 2.
  
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3. Figure 2: Reaction scheme for the synthesis of rhodamine-appended β-CD.
  
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4. Figure 3: TLC plates at different development stages for monitoring the composition of Rho-β-CD crude (left p...
  
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5. Figure 4: ¹H NMR spectrum of Rho-β-CD with partial assignments (D₂O, 500 MHz, 298 K).
  
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6. Figure 5: Expansion of DEPT-ed-HSQC spectrum of Rho-β-CD with partial assignments (D₂O, 500 MHz, 298 K).
  
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7. Figure 6: Cartoon models for the possible intermolecular inclusion mode of Rho-β-CD in solution (3D perspecti...
  
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8. Figure 7: ¹H NMR spectrum of Flu-β-CD with partial assignments (D₂O, 500 MHz, 298 K).
  
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9. Figure 8: Cartoon models for the possible intermolecular inclusion mode of Flu-β-CD in solution (3D perspecti...
  
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Beilstein J. Org. Chem. 2016, 12, 537–548, doi:10.3762/bjoc.12.53

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Supramolecular structures based on regioisomers of cinnamyl-α-cyclodextrins – new media for capillary separation techniques

Gabor Benkovics,
Ondrej Hodek,
Martina Havlikova,
Zuzana Bosakova,
Pavel Coufal,
Milo Malanga,
Eva Fenyvesi,
Andras Darcsi,
Szabolcs Beni and
Jindrich Jindrich

Full Research Paper
Published 19 Jan 2016

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1. Graphical Abstract
2. Figure 1: Example of elucidation of 2D NMR spectra of 2-O-Cin-α-CD.
  
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3. Figure 2: 2D ROESY spectrum of 2-O-Cin-α-CD in D₂O at 25 °C at 24 mM concentration.
  
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4. Figure 3: Expansion of the 2D ROESY spectrum of 2-O-Cin-α-CD indicating the geometric arrangement.
  
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5. Figure 4: ¹H NMR spectra of 2-O-Cin-α-CD in D₂O at 25 °C at different concentrations.
  
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6. Figure 5: ¹H NMR spectra of 3-O-Cin-α-CD in D₂O at 25 °C recorded at various concentrations.
  
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7. Figure 6: Diffusion coefficients of 2-O-Cin-α-CD (black) and, 3-O-Cin-α-CD (red) in D₂O at various concentrat...
  
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8. Figure 7: Effect of solvent on the size distribution of aggregates formed by 2-O-Cin-α-CD at 25 °C (the appli...
  
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9. Figure 8: Effect of a solvent on the size distribution of aggregates formed by 3-O-Cin-α-CD at 25 °C (the app...
  
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10. Figure 9: Aggregate sizes (diameter) of 2-O-Cin-α-CD (black) and 3-O-Cin-α-CD (red) in water at various tempe...
  
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11. Figure 10: Schematic representation of the DLS experiment proving the host–guest nature of the aggregate forma...
  
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12. Figure 11: The effect of competitive additives on the size distribution of aggregates formed by 3-O-Cin-α-CD a...
  
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13. Figure 12: Expansion of the 2D ROESY spectrum of 2-O-Cin-α-CD in the presence of CioOK as competitive guest mo...
  
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14. Figure 13: ¹H NMR spectrum of 2-O-Cin-α-CD before (up) and after (down) the addition of CioOK in 5-fold molar ...
  
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15. Figure 14: The influence of 5 mM 2-O-Cin-α-CD in BGE (right column) on the decrease of the effective electroph...
  
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Beilstein J. Org. Chem. 2016, 12, 97–109, doi:10.3762/bjoc.12.11

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Synthetic strategies for the fluorescent labeling of epichlorohydrin-branched cyclodextrin polymers

Milo Malanga,
Mihály Bálint,
István Puskás,
Kata Tuza,
Tamás Sohajda,
László Jicsinszky,
Lajos Szente and
Éva Fenyvesi

Full Research Paper
Published 16 Dec 2014

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1. Graphical Abstract
2. Scheme 1: Schematic representation of the various synthetic routes for the introduction of an anchoring group...
  
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3. Scheme 2: Synthetic strategy for the rhodaminylation of β-CD polymer.
  
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4. Figure 1: TLC study of β-CD iodination showing the proceeding of 6-monoiodination with increasing reaction ti...
  
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5. Figure 2: HSQC-DEPT spectrum of compound 1 with partial assignment.
  
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6. Figure 3: IR spectra of compound 1 (black line) and compound 2 (red line) showing the disappearance of the az...
  
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7. Scheme 3: Schematic representation for the coumarinylation of methylated β-CD-polymer, n, m, p and q mean the...
  
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8. Figure 4: HSQC-DEPT spectra of compound 4 with partial assignment; in the upper part the full spectrum is sho...
  
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9. Scheme 4: Schematic representation for the introduction of NBF in a cationic β-CD-polymer.
  
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10. Scheme 5: Schematic representation for the introduction of fluorescein into a β-CD-polymer.
  
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Beilstein J. Org. Chem. 2014, 10, 3007–3018, doi:10.3762/bjoc.10.319

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