One-pot synthesis of hybrid macrocyclic pentamers with variable functionalizations around the periphery |
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Authors: | Qin Bo Sun Chang Liu Ying Shen Jie Ye Ruijuan Zhu Jia Duan Xin-Fang Zeng Huaqiang |
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Institution: | Department of Chemistry and NUS MedChem Program of the Office of Life Sciences, 3 Science Drive 3, National University of Singapore, Singapore 117543, China. |
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Abstract: | Rather than four- or six-residue macrocylces, one-pot macrocyclization allows for the highly selective formation of five-residue macrocycles rigidified by intramolecular hydrogen bonds. Variable functionalizations around the pentameric periphery were achieved by reacting monomers with higher oligomers bearing different exterior side chains. The formation of these hybrid pentamers suggests a chain-growth mechanism for the one-pot macrocyclization where the successive addition of monomers onto higher oligomers is faster than those between two monomers or two higher oligomers. |
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