Controlled Decoration of [60]Fullerene with Polymannan Analogues and Amino Acid Derivatives through Malondiamide-Based Linkers
Abstract
:1. Introduction
2. Results
2.1. Synthesis of Propargyl-Mannose Glycans
2.2. Preparation of Glycosylated C60 Derivatives
2.3. Conjugation of C60 with Amino Acid Derivatives
2.4. Double Conjugation of C60: Sugar and Amino Acid Derivative
3. Conclusions
4. Materials and Methods
4.1. Sugar Synthesis
- Propargyl 2″,3″,4″,6″-tetra-O-acetyl-α-d-mannopyranosyl-(1→6)-2′,3′,4′-tri-O-acetyl-α-d-mannopyranosyl-(1→6)-2,3,4-tri-O-acetyl-α-d-mannopyranoside (7)
4.2. Functionalization of C60 with Sugar Derivatives
- 3-azidopropan-1-amine (8) [54]
- N1,N3-bis(3-azidopropyl)malondiamide (9)
- Man malondiamide chain (10)
- Man(α1,6)man malondiamide chain (11)
- Man(α1,2)man malondiamide chain (12)
- Man(α1,6)man(α1,6)man malondiamide chain (13)
- Fullerene-man (14)
- Fullerene-man(α1,6)man (15)
- Fullerene-man(α1,2)man (16)
- Fullerene-man(α1,6)man(α1,6)man (17)
4.3. Functionalization of C60 with Amino Acid Derivatives
- Methyl hex-5-ynoyl-l-alaninate (18)
- Dimethyl 2,2′-((4,4′-(((malonylbis(azanediyl))bis(propane-3,1-diyl))bis(1H-1,2,3-triazole-1,4-diyl))bis(butanoyl))bis(azanediyl))dipropionate (19)
- Fullerene-l-alanine (20)
- Methyl 2-(hex-5-ynamido)-2-methylpropanoate (21)
- Dimethyl 2,2′-((4,4′-(((malonylbis(azanediyl))bis(propane-3,1-diyl))bis(1H-1,2,3-triazole-1,4-diyl))bis(butanoyl))bis(azanediyl))bis(2-methylpropanoate) (22)
- Fullerene–Aib (23)
4.4. Double Functionalization of C60
- Fullerene–man–Aib (24)
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Acknowledgments
Conflicts of Interest
Sample Availability
References
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Compound | Entry | Ratio (C60:Sugar) | Temperature | Time | Yield |
---|---|---|---|---|---|
14 | 1 | 1:1 | rt | 1.5 h | 17% |
2 | 1:1 | rt | 1 h | 30% | |
3 | 1:1 | rt | 45 min | 41% | |
15 | 4 | 1:1 | rt | 1.5 h | 10% |
5 | 1:1 | rt | 1 h | 12% | |
6 | 1:1 | rt | 30 min | 16% | |
7 | 1:1 | rt | 15 min | 22% | |
8 | 1:1 | rt | 7 min | 24% | |
9 | 1:1 | 0 °C | 20 min | 26% | |
10 | 1:1 | 0 °C | 1 h | 30% | |
11 | 1:1 | 0 °C | 2 h | 31% | |
16 | 12 | 1:1 | 0 °C | 1 h | 8% |
13 | 1:1 | −20 °C | 3 h | 8% | |
14 | 1:1 | −20 °C | 1.5 h | <5% | |
15 | 1:1 | rt | 3 h | 11% | |
16 | 1:1 | rt | 1.5 h | 10% | |
17 | 1:1 | rt | 6 h | 5% | |
18 | 1:0.7 | rt | 1 h | 5% | |
17 | 19 | 1:1 | 0 °C | 1 h | 12% |
20 | 1:1 | 0 °C | 20 min | 15% | |
21 | 1:1 | 0 °C | 10 min | 13% | |
22 | 1:1 | rt | 15 min | 12% |
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Tanzi, L.; Rubes, D.; Bavaro, T.; Sollogoub, M.; Serra, M.; Zhang, Y.; Terreni, M. Controlled Decoration of [60]Fullerene with Polymannan Analogues and Amino Acid Derivatives through Malondiamide-Based Linkers. Molecules 2022, 27, 2776. https://doi.org/10.3390/molecules27092776
Tanzi L, Rubes D, Bavaro T, Sollogoub M, Serra M, Zhang Y, Terreni M. Controlled Decoration of [60]Fullerene with Polymannan Analogues and Amino Acid Derivatives through Malondiamide-Based Linkers. Molecules. 2022; 27(9):2776. https://doi.org/10.3390/molecules27092776
Chicago/Turabian StyleTanzi, Lisa, Davide Rubes, Teodora Bavaro, Matthieu Sollogoub, Massimo Serra, Yongmin Zhang, and Marco Terreni. 2022. "Controlled Decoration of [60]Fullerene with Polymannan Analogues and Amino Acid Derivatives through Malondiamide-Based Linkers" Molecules 27, no. 9: 2776. https://doi.org/10.3390/molecules27092776