An NMR study of eremomycin and its derivatives. Full 1H and 13C assignment, motional behavior, dimerization and complexation with Ac-D-Ala-D-Ala.
Complete 1H and 13C NMR assignments are presented for eremomycin (1) and some of its desglycosylated derivatives 2, 3 and compared to the structurally closely related glycopeptide vancomycin. Primary structure and stereochemistry of eremomycin is corroborated by the present high field total correlation spectroscopy, NOESY and heteronuclear multiple-bond correlation NMR methods. A rough motional characterization of the title compound is attempted by 13C-T1 and 13C-[1H] NOE measurements. Dimerization of eremomycin is observed both in DMSO-d6-CCl4 and D2O solutions. Complexation with cell wall analogue dipeptide Ac-D-Ala-D-Ala is also demonstrated.
Batta
G
G
Research Group for Antibiotics, Hungarian Academy of Sciences, Debrecen.
Sztaricskai
F
F
Kövér
K E
KE
Rüdel
C
C
Berdnikova
T F
TF
D000900:Anti-Bacterial Agents / Q000737:chemistry*; D006020:Glycopeptides / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D014640:Vancomycin / Q000737:chemistry
D000900:Anti-Bacterial Agents; D006020:Glycopeptides; C053759:eremomycin; D014640:Vancomycin