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Tetrahydropyran‐Amino Acids: Novel Building Blocks for Gramicidin‐Hybrid Ion Channels
Author(s) -
Schröder Sabine,
Schrey Anna K.,
Knoll Andrea,
Reiß Philipp,
Ziemer Burkhard,
Koert Ulrich
Publication year - 2006
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200600068
Subject(s) - chemistry , tetrahydropyran , ion channel , amino acid , gramicidin , stereoselectivity , ion , stereochemistry , selectivity , peptide , organic chemistry , ring (chemistry) , biochemistry , receptor , catalysis , membrane
The stereoselective synthesis of a cis ‐2,6‐disubstituted tetrahydropyran bearing a δ‐amino acid has been achieved starting from N ‐Boc‐leucinal. The THP amino acid was incorporated into peptide sequences and the structural consequences were studied by X‐ray crystallography and NMR analysis. Single‐channel current measurements showed that the THP amino acid is a suitable substitute for positions 11 and 12 of the gramicidin ion channel. The resulting hybrid ion channel revealed Eisenman I ion selectivity and an ion‐dependence of the channel dwell time. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)