Preparation of Functional Monomers as Precursors of Bioprobes from a Common Styrene Derivative and Polymer Synthesis
Abstract
:1. Introduction
2. Results and Discussion
2.1. Conversion of 4-(Chloromethyl)styrene into an Amine as a Common Precursor
2.2. Synthetic Conversion of the Amine into Functionalized Monomers
2.3. Preparation of a Carbohydrate Monomer
2.4. Polymerization of a Glycomonomer by Means of Radical Polymerization
2.5. Biological Evaluations of the Glycopolymers for Lectin
3. Experimental
3.1. Materials and Methods
3.2. Synthesis
3.2.1. 4-Azidomethylstyrene (AZ-Str) (2)
3.2.2. Aminomethylstyrene (AMN-Str) (3)
3.2.3. 4-{[5-(Dimethylamino)-1-naphthalenesulfonamido]methyl}styrene (DSL-Str) (4)
3.2.4. 4-({5-[(3aR,6S,6aS)-2-Oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-6-yl]pentanamido}methyl)-styrene (BTN-Str) (5)
3.2.5. 2-[2-(2-Hydroxyethoxy)-ethoxy]-ethyl-O-2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-d-glucopyranoside (7)
3.2.6. 8-O-(2-Acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-d-glucopyranosyl)-3,6-dioxaoctanoic Acid (8)
3.2.7. 8-O-(2-Acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-d-glucopyranosyl)-3,6-dioxaoctanoic Acid 4-vinybenzylamide (9)
3.2.8. 8-O-(2-Acetamido-2-deoxy-β-d-glucopyranosyl)-3,6-dioxaoctanoic acid 4-vinybenzylamide (NAG-Str) (10)
3.3. Radical Polymerization
3.4. Biological Evaluations of Glycopolymers for WGA
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Acknowledgments
Conflicts of Interest
References
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Sample Availability: Samples of the compounds 2, 4, 5 and 10 are available from the authors. |
Reagent | Solvent | Temp (°C) | Time (h) | Yield (%) |
---|---|---|---|---|
DIC | DMF | Rt | on | 0 |
EDC | DMF | Rt | 5 | 0 |
BOP | CH3CN | Rt | 3 | 36 1 |
BOP | DMF | Rt | 1.5 | 17 1 |
DMT-MM | DMF | Rt | 2 | 91 |
Monomer Ratio 10:AAm | Polymer | Time (h) | Solvent | Total Yield 1 (%) | Polymer Composition 2 x:y:n | Sugar Content (wt%) | D4 | |
---|---|---|---|---|---|---|---|---|
1:0 | 11a | 69 | H2O | 71 | 1:0:6.5 × 10 2 | 100 | 315 | 1.13 |
1:4 | 11b | 24 | H2O | 81 | 1:4:6.2 × 10 2 | 63 | 472 | 1.01 |
1:10 | 11c | 24 | H2O | 99 | 1:11:1.5 × 10 2 | 38 | 183 | 2.52 |
1:20 | 11d | 24 | H2O | 90 | 1:22:1.5 × 10 2 | 24 | 297 | 1.34 |
Compounds | Δλ (nm) | |ΔF′/F0| (%) | Ka (M−1) | Relative Potency |
---|---|---|---|---|
GlcNAc | 0 | 5 | 8.2 × 103 | 1 |
10 | - | 90 | 5.0 × 104 | 6 |
11a | −14.2 | 33 | 1.8 × 105 | 22 |
11b | −14.2 | 46 | 3.7 × 105 | 45 |
11c | −13.0 | 50 | 3.5 × 105 | 43 |
11d | −16.0 | 58 | 4.2 × 105 | 51 |
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Hayama, R.; Koyama, T.; Matsushita, T.; Hatano, K.; Matsuoka, K. Preparation of Functional Monomers as Precursors of Bioprobes from a Common Styrene Derivative and Polymer Synthesis. Molecules 2018, 23, 2875. https://doi.org/10.3390/molecules23112875
Hayama R, Koyama T, Matsushita T, Hatano K, Matsuoka K. Preparation of Functional Monomers as Precursors of Bioprobes from a Common Styrene Derivative and Polymer Synthesis. Molecules. 2018; 23(11):2875. https://doi.org/10.3390/molecules23112875
Chicago/Turabian StyleHayama, Riho, Tetsuo Koyama, Takahiko Matsushita, Ken Hatano, and Koji Matsuoka. 2018. "Preparation of Functional Monomers as Precursors of Bioprobes from a Common Styrene Derivative and Polymer Synthesis" Molecules 23, no. 11: 2875. https://doi.org/10.3390/molecules23112875