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A Direct One-Pot Modification of β-Cyclodextrin via the Ugi-Five-Component Reaction

Schneider, Rebekka V.; Sehlinger, Ansgar; Meier, Michael A. R.

Abstract:
Starch‐derived β‐cyclodextrins (β‐CDs) are used in pharmacy or the food and cosmetic industry as drug deliverers, separating agents, catalysts, detergents, or viscosity modifiers. However, solubility issues often restrict their potential applications. Here, we report a straightforward and direct one‐pot synthesis for the modification of β‐CDs based on the Ugi‐five‐component reaction (Ugi‐5CR). The Ugi‐5CR requires to react an amine, an aldehyde, an isocyanide, carbon dioxide and the β‐CD, which serves as alcohol component. Overall, five modified β‐CDs containing carbamate moieties were synthesized at room temperature in a high pressure reactor (10 bar) within 24 hours. The successful modifications are verified by mass spectrometry, nuclear magnetic resonance, and infrared spectroscopy, indicating one to three reacted primary hydroxyl groups per β‐CD. Additionally, we report altered solubility behavior of two of the five modified β‐CDs.

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Verlagsausgabe §
DOI: 10.5445/IR/1000125237
Veröffentlicht am 23.10.2020
Cover der Publikation
Zugehörige Institution(en) am KIT Institut für Organische Chemie (IOC)
Institut für Biologische und Chemische Systeme (IBCS)
Publikationstyp Zeitschriftenaufsatz
Publikationsdatum 14.09.2020
Sprache Englisch
Identifikator ISSN: 2365-6549
KITopen-ID: 1000125237
HGF-Programm 47.01.01 (POF III, LK 01)
Biol.Netzwerke u.Synth.Regulat. ITG+ITC
Erschienen in ChemistrySelect
Band 5
Heft 34
Seiten 10765-10770
Vorab online veröffentlicht am 10.09.2020
Nachgewiesen in Scopus
Web of Science
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