Molecular Recognition in Methanol: The First Example of Hydrogen-Bond-Mediated Self-Association of a Calix[4]arene in Polar, Protic Solvent

Autor:	Suzanne Beckham Shuker, R. Elizabeth Brewster
Rok vydání:	2002
Předmět:	chemistry.chemical_classification Chemistry Hydrogen bond Dimer General Chemistry Biochemistry Catalysis Amino acid Solvent chemistry.chemical_compound Colloid and Surface Chemistry Molecular recognition Calixarene Polymer chemistry Organic chemistry Methanol Protic solvent
Zdroj:	Journal of the American Chemical Society. 124:7902-7903
ISSN:	1520-5126 0002-7863
Popis:	Tetraalaninecalixarene was prepared by coupling of tetraaminocalix[4]arene with alanine. It dimerizes in methanol, providing the first example of a substituted calixarene that undergoes self-association through hydrogen bonding in polar, protic solvent. The association constant in 24:1 MeOH:H2O was determined to be 29 000 M-1. Addition of arginine or lysine results in disruption of the dimer and formation of a 1:1 complex between the amino acid and the tetraalaninecalixarene. The preparation of a peptidocalixarene that associates in polar solvent opens new doors for the use of calixarenes for molecular recognition in biologically relevant environments.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::fd7c5251dc37b9b6ec73af5cb3e9d4cb https://doi.org/10.1021/ja026084o Zobrazit plný text záznamu