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Suman Kumar Ghosh
복잡계 자기조립 연구단
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Superacid-Mediated Functionalization of Hydroxylated Cucurbit[ n]urils

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Title
Superacid-Mediated Functionalization of Hydroxylated Cucurbit[ n]urils
Author(s)
Suman Kr Ghosh; Avinash Dhamija; Young Ho Ko; An J.; Moon Young Hur; Deepak Ramdas Boraste; Seo J.; Eunsung Lee; Kyeng Min Park; Kimoon Kim
Publication Date
2019-11
Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, v.141, no.44, pp.17503 - 17506
Publisher
AMER CHEMICAL SOC
Abstract
© 2019 American Chemical Society.Herein we report a facile transformation of hydroxylated cucurbit[n]uril (CB[n], n = 6 and 7) to other functionality-conjugated CB[n]s by nucleophilic substitution of the hydroxyl group with a wide range of nitriles and alcohols. The reaction proceeds efficiently via generation of a superelectrophilic carbocation on the CB framework from hydroxylated CB[n]s under superacidic conditions. One of the resulting CB[n] derivatives with reactive functionality, monocarboxylated CB[7], is efficiently conjugated to an enzyme (horseradish peroxidase, HRP) by amide coupling. This provides a CB[7]-conjugated functional biomaterial (CB[7]-HRP) that selectively detects proteins labeled with a guest, adamantylammonium (AdA), based on bioorthogonal high-affinity host-guest interactions between CB[7] and AdA. We demonstrated the potential of overcoming the limitations in preparing reactive functional CB[n] derivatives, enabling the exploration of novel bioapplications of CB[n]-based host-guest chemistry with new CB[n]-conjugated functional materials
URI
https://pr.ibs.re.kr/handle/8788114/6812
ISSN
0002-7863
Appears in Collections:
Center for Self-assembly and Complexity(복잡계 자기조립 연구단) > Journal Papers (저널논문)
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