A calix[4]arene ureidopeptide dimer self-assembled through two superposed hydrogen bond arrays

Authors
Rincon, AM Prados, P de Mendoza, J
Citation
Am. Rincon et al., A calix[4]arene ureidopeptide dimer self-assembled through two superposed hydrogen bond arrays, J AM CHEM S, 123(15), 2001, pp. 3493-3498
Citations number
30
Categorie Soggetti
Chemistry & Analysis",Chemistry
Journal title
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
ISSN journal
00027863 → ACNP
Volume
123
Issue
15
Year of publication
2001
Pages
3493 - 3498
Database
ISI
SICI code
0002-7863(20010418)123:15<3493:ACUDST>2.0.ZU;2-T
Abstract
Dimerization of calix[4]arene ureidopeptides is demonstrated for the first time. Two calix[4]arenes tetrasubstituted in the upper rim with -NHCONH(L)L euNHC(8)H(17) (I) and -NHCONH(L)Leu(D)Leu-OMe (2) were prepared and studied by NMR, circular dicroism, and gel permeation chromatography. Compound 2 s elf-assembles through urea-urea hydrogen bonds, as well as by an additional set of hydrogen bonds provided by the peptide side chains, with participat ion of the eater carbonyls. The absence of such group in 1 causes the monom er structure to be favored in this case.