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The C‐Terminal Heptapeptides of Suzukacillin A and Alamethicin F30 — Sequence, Conformation, and Synthesis
Author(s) -
Katz Ellen,
Schmitt Heribert,
Jung Günther,
Aydin Mitat,
König Wilfried A.
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.198519850212
Subject(s) - alamethicin , chemistry , sequence (biology) , stereochemistry , microbiology and biotechnology , membrane , biochemistry , biology , lipid bilayer
During the sequencing of the membrane‐modifying eicosapeptide antibiotic suzukacillin A two C‐terminal heptapeptides were obtained via selective trifluoroacetolysis: L‐Pro‐L‐Val‐Aib‐D‐Iva‐L‐Gln‐L‐Gln‐L‐Phl and ‐Pro‐L‐Val‐Aib‐Aib‐L‐Gln‐L‐Phl. The chromatographic and spectroscopic comparison (FAB MS, FD MS, 13 C NMR, CD, UV) of these isolated natural fragments with the synthetic segment L‐Pro‐L‐Val‐Aib‐Aib‐L‐Gln‐L‐Gln‐L‐Phl ( 2 ) and the synthetic C‐terminal segment of alamethicin F30 L‐Pro‐L‐Val‐Aib‐Aib‐L‐Glu‐L‐Gln‐L‐Phl ( 1 ) proved the sequence 14‐20 of suzukacillin A.