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Structure of the Adduct of Alantolactone with ( Z )‐ L ‐Cys‐Ala‐OMe; 1 H and 13 C Assignment of the Alantolactone Moiety by NMR at 14 T
Author(s) -
Ginanneschi Mauro,
Chelli Mario,
Maria Papini Anna,
Pinzani Daniela,
Rapi Gianfranco
Publication year - 1996
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/(sici)1097-458x(199602)34:2<95::aid-omr855>3.0.co;2-v
Subject(s) - chemistry , moiety , adduct , stereochemistry , two dimensional nuclear magnetic resonance spectroscopy , dipeptide , alanine , proton nmr , peptide , amino acid , organic chemistry , biochemistry
Analysis of the 1 H– 1 H NOE effects observed for S ‐(11,13‐dihydroalantolacton‐13‐yl)‐L‐cysteinyl‐L‐alanine methyl ester in (CD 3 ) 2 SO at 14 T showed that the 7‐ and 11‐protons are in cis positions. The distances between 7‐, 8‐ and 11‐protons of the adduct were derived by a semi‐quantitative approach based on analysis of NOESY cross peaks and a computed molecular model. The simulated 1 H spectrum of the alantolactone moiety is in excellent agreement with the experimental data. The complete assignments of the 13 C signals of alantolactone, its peptide adduct and four dipeptide precursors are based on one‐ and two‐dimensional 1 H– 13 C NMR techniques.