p-Octiphenyl β-Barrels with Ion Channel and Esterase Activity

Baumeister, Bodo; Sakai, Naomi; Matile, Stefan

doi:10.1021/ol016914n

Scientific article

Letter

English

p-Octiphenyl β-Barrels with Ion Channel and Esterase Activity

Contributors

Baumeister, Bodo; Sakai, Naomi

; Matile, Stefan

Published in

Organic letters, vol. 3, no. 26, p. 4229-4232

Publication date

2001

Abstract

Design, synthesis, and esterase and ion channel activity of a novel barrel-stave supramolecule with hydrophobic exterior and histidine-rich interior are reported. Voltage-dependent binding of pyrenyl-8-oxy-1,3,6-trisulfonates by histidines within p-octiphenyl beta-barrels (and not monomers) via ionic (and not hydrophobic) interactions (K(D), K(I), K(M) < 1 microM) is the basis for superb esterolytic proficiency up to (k(cat)/K(M))/k(uncat) = 9.6 x 10(5) in water and bilayer membranes. The conductance of labile ion channels formed in planar bilayer membranes is shown to be reduced by 8-hydroxypyrene-1,3,6-trisulfonate on the single- and multichannel level.

UNIGE affiliation entities

Faculté des sciences / Section de chimie et biochimie / Département de chimie organique

Citation (ISO format)

BAUMEISTER, Bodo, SAKAI, Naomi, MATILE, Stefan. p-Octiphenyl β-Barrels with Ion Channel and Esterase Activity. In: Organic letters, 2001, vol. 3, n° 26, p. 4229–4232. doi: 10.1021/ol016914n

Article

Identifiers

PID : unige:6956
DOI : 10.1021/ol016914n
PMID : 11784184

Journal ISSN

1523-7052

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p-Octiphenyl β-Barrels with Ion Channel and Esterase Activity

Contributors

Published in

Publication date

Abstract

UNIGE affiliation entities

Citation (ISO format)

Main files (1)

Identifiers

Journal ISSN

Technical informations

Creation

First validation

Update

Status update

Last indexation