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Scientific article
English

Rigid-Rod ß-Barrels as Lipocalin Models: Probing Confined Space by Carotenoid Encapsulation

Contributors

Baumeister, Bodo; Matile, Stefan

Published in

Chemistry, vol. 6, no. 10, p. 1739-1749

Publication date

2000

Abstract

Herein, we describe the design, synthesis, structure, and function of synthetic, supramolecular ß-barrel models. Assembly of octi(p-phenylene)s with complementary -Lys-Leu-Lys-NH2 and -Glu-Leu-Glu-NH2 side chains yielded water-soluble rigid-rod ß-barrels of precise length and with flexible diameter. A hydrophobic interior was evidenced by guest encapsulation. Host-guest complexes with planarized, monomeric ß-carotene within tetrameric rigid-rod ß-barrels, and disc micellar astaxanthin J-aggregates surrounded by about dodecameric rigid-rod bicycle tires were prepared from mixed micelles by dialytic detergent removal. The significance of these findings for future bioorganic chemistry in confined, intratoroidal space is discussed in comparison with pertinent biological examples.

Keywords

  • Bioorganic chemistry
  • Cage compounds
  • Carotenoids
  • Oligomers
  • Peptidomimetics

UNIGE affiliation entities

Citation (ISO format)

BAUMEISTER, Bodo, MATILE, Stefan. Rigid-Rod ß-Barrels as Lipocalin Models: Probing Confined Space by Carotenoid Encapsulation. In: Chemistry, 2000, vol. 6, n° 10, p. 1739–1749. doi: 10.1002/(SICI)1521-3765(20000515)6:10<1739::AID-CHEM1739>3.0.CO;2-Y

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Article

Identifiers

Journal ISSN

0947-6539
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Technical informations

Creation

21/06/2010 10:27:37

First validation

21/06/2010 10:27:37

Update

14/10/2025 06:56:37

Status update

14/03/2023 15:46:35

Last indexation

02/11/2025 20:15:10
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