Functionalized Calixspherands: Synthesis and Peptide Coupling

• Published in: Journal of organic chemistry Vol. 59; no. 5; pp. 972 - 976
• Main Authors: Iwema Baker, Wouter I, Haas, Marijke, den Hertog, Herman J, Verboom, Willem, de Zeeuw, Dick, Bruins, Andries P, Reinhoudt, David N
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 01.03.1994; Amer Chemical Soc
• Subjects: Chemistry; Chemistry, Organic; Exact sciences and technology; Heterocyclic compounds; Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives; Organic chemistry; Physical Sciences; Preparations and properties; Science & Technology; HOST GUEST COMPLEXATION; ACID; MOLECULAR-WEIGHT PROTEINS; CALIX ARENES; HEMISPHERANDS; CATIONS; Enzyme; Carboxylic acid; Glycosidases; Hydrolases; Peptide synthesis; Calixarene; Cyclophane; Oxygen heterocycle; O-Glycosidases; Lysozyme; Chemical coupling; Macrocycle
• ISSN: 0022-3263; 1520-6904
• DOI: 10.1021/jo00084a011

Calixspherands, like 1, form kinetically stable complexes with alkali metal cations. For practical in vivo applications coupling of these complexes with carrier molecules is mandatory, Therefore, a general method for the synthesis of functionalized calixspherand 17 was developed starting from functionalized m-terphenyl 10 and p-tert-butylcalix[4]arene (14). The functionalized m-terphenyl was synthesized by a Suzuki-cross-coupling reaction. Functionalized calixspherand 17 has been coupled to a low molecular weight protein.