Heterofunctionalized Cavitands by Macrocyclization of Sequence-Defined Foldamers

Joseph W. Meisel; Chunhua T. Hu; Andrew D. Hamilton

doi:10.1021/acs.orglett.9b02708

Heterofunctionalized Cavitands by Macrocyclization of Sequence-Defined Foldamers

Joseph W. Meisel, Chunhua T. Hu, Andrew D. Hamilton

Chemistry

Research output: Contribution to journal › Article › peer-review

Abstract

Macrocyclic hosts have long been the workhorses of molecular recognition. Despite the widespread use of container-shaped molecules as synthetic receptors, an efficient preparation of cavitands bearing multiple functional groups has not been realized. This Letter describes a new cavitand derived from a sequence-defined oligoamide foldamer scaffold. A solid-phase synthesis approach is reported, which enables the display of multiple chemically diverse functional groups on the cavitand rim.

Original language	English (US)
Pages (from-to)	7763-7767
Number of pages	5
Journal	Organic Letters
Volume	21
Issue number	19
DOIs	https://doi.org/10.1021/acs.orglett.9b02708
State	Published - Oct 4 2019

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.9b02708

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title = "Heterofunctionalized Cavitands by Macrocyclization of Sequence-Defined Foldamers",

abstract = "Macrocyclic hosts have long been the workhorses of molecular recognition. Despite the widespread use of container-shaped molecules as synthetic receptors, an efficient preparation of cavitands bearing multiple functional groups has not been realized. This Letter describes a new cavitand derived from a sequence-defined oligoamide foldamer scaffold. A solid-phase synthesis approach is reported, which enables the display of multiple chemically diverse functional groups on the cavitand rim.",

author = "Meisel, {Joseph W.} and Hu, {Chunhua T.} and Hamilton, {Andrew D.}",

note = "Funding Information: We thank NYU for funding to A.D.H. and the National Institute of General Medical Sciences of the National Institutes of Health (F32GM126851) for funding to J.W.M. We are thankful for the support of the X-ray facility from the Materials Research Science and Engineering Center (MRSEC) program of the National Science Foundation (NSF) under Award Numbers DMR-0820341 and DMR-1420073. Publisher Copyright: {\textcopyright} 2019 American Chemical Society.",

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doi = "10.1021/acs.orglett.9b02708",

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N2 - Macrocyclic hosts have long been the workhorses of molecular recognition. Despite the widespread use of container-shaped molecules as synthetic receptors, an efficient preparation of cavitands bearing multiple functional groups has not been realized. This Letter describes a new cavitand derived from a sequence-defined oligoamide foldamer scaffold. A solid-phase synthesis approach is reported, which enables the display of multiple chemically diverse functional groups on the cavitand rim.

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Heterofunctionalized Cavitands by Macrocyclization of Sequence-Defined Foldamers

Abstract

ASJC Scopus subject areas

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