Synthesis and ionic channels of a linear gramicidin containing naphthylalanine instead of tryptophan

Naphthylalanine gramicidin A was prepared by the solid phase method using an aminopolyacrylic resin after optical resolution of (D, L) naphthylalanine by enzymatic methods. Removal of the peptide from the resin was achieved by transesterification of the succinic ester linkage. Infrared spectroscopy...

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Bibliographic Details
Published in:	International journal of peptide and protein research Vol. 33; no. 4; p. 273
Main Authors:	Ranjalahy-Rasoloarijao, L, Lazaro, R, Daumas, P, Heitz, F
Format:	Journal Article
Language:	English
Published:	Denmark 01-04-1989
Subjects:	1-Naphthylamine Gramicidin - chemical synthesis Indicators and Reagents Ion Channels - physiology Magnetic Resonance Spectroscopy Models, Theoretical Naphthalenes Protein Conformation Tryptophan
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Summary:	Naphthylalanine gramicidin A was prepared by the solid phase method using an aminopolyacrylic resin after optical resolution of (D, L) naphthylalanine by enzymatic methods. Removal of the peptide from the resin was achieved by transesterification of the succinic ester linkage. Infrared spectroscopy indicated that the presence of naphthylalanine strongly modifies the monomer-dimer equilibrium. Single-channel measurements suggested that the conductance of the gramicidin channel can be governed by the dipole moment of the aromatic side-chains.
ISSN:	0367-8377
DOI:	10.1111/j.1399-3011.1989.tb01282.x