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13 C NMR Spectroscopic Control of the Synthesis of Alamethicin F 30 and its Segments
Author(s) -
Schmitt Heribert,
Jung Günther
Publication year - 1985
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.198519850211
Subject(s) - alamethicin , chemistry , nuclear magnetic resonance spectroscopy , circular dichroism , spectroscopy , spectral line , nmr spectra database , crystallography , two dimensional nuclear magnetic resonance spectroscopy , analytical chemistry (journal) , nuclear magnetic resonance , stereochemistry , membrane , chromatography , biochemistry , lipid bilayer , physics , quantum mechanics , astronomy
All segments built up for the total synthesis of the α‐helical antibiotic alamethicin F 30 ( 1 ) were investigated by 13 C NMR spectroscopy of methanolic solutions. With a few exceptions the signals were unequivocally assignable by comparison with spectra of related peptides, by coupled spectra and J ‐modulated spin‐echo experiments. For the first time a synthetic and highly pure alamethicin F 30 preparation could be studied by 13 C NMR spectroscopy at 100.6 MHz. All results were in full agreement with the synthesized intermediates and the final product, and with their conformations as derived from circular dichroism and X‐ray analysis. Partially there is a striking retention of conformation from smaller to larger segments.