Premium
Assignment of All Proton, Carbon, and Nitrogen NMR Signals of Antamanide in Chloroform Solution
Author(s) -
Kessler Horst,
Müller Arndt,
Pook KarlHeinz
Publication year - 1989
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.198919890242
Subject(s) - heteronuclear molecule , chemistry , chloroform , protonation , proton , phenylalanine , nuclear magnetic resonance spectroscopy , sequence (biology) , proton nmr , pulse sequence , nmr spectra database , spectral line , stereochemistry , crystallography , amino acid , nuclear magnetic resonance , organic chemistry , biochemistry , physics , ion , quantum mechanics , astronomy
Homo‐ and heteronuclear one‐ and two‐dimensional techniques have been used to assign the 1 H, 13 C, and 15 N NMR spectra of the cyclic decapeptide antamanide ( 1 ) in CDCl 3 . The assignment includes the aromatic resonances of phenylalanine and the non‐protonated nitrogen atoms of proline by means of heteronuclear two‐dimensional NMR spectroscopy. Sequence analysis of the four phenylalanine and four proline amino acid residues was performed by heteronuclear proton – carbon long‐range couplings using the COLOC sequence. Three new thiazolidine analogues of antamanide confirm the sequence analysis of prolines and open the possibility for the extraction of extended spectral parameters. The interpretation of NOE data, obtained from one‐ and two‐dimensional spectra at high field and low temperatures, demonstrate possible misinterpretations of this effect respecting sequence assignment, if only NOEs between NH protons and α‐protons are considered.