Two-dimensional proton J-resolved NMR spectroscopy of neomycin B
The /sup 1/H NMR spectrum of a solution of neomycin B free base (Structure 1) in D/sub 2/O has been assigned completely by two-dimensional, homonuclear J-resolved NMR spectroscopy and spin decoupling at 400 MHz. Proton chemical shifts and proton-proton couplings are reported for all glycoside residues in neomycin B along with their computer simulated spectra. The /sup 4/C/sub 1/ chair conformation has been assigned to the 2,6-diamino-2,6-dideoxy-..beta..-L-idopyranosyl (ring D) portion of the antibiotic (1b) by analysis of the proton coupling constants and chemical shifts. The ..beta..-furanose form of the ribosyl portion (ring C) has been assigned. Vicinal proton couplings for the 2-deoxystreptaminyl group (ring B) are consistent with a chair conformation in which all ring substituents are equatorial, and proton chemical shift assignments are based on protonation studies. A computer simulated composite of the individual calculated spectra is presented for comparison with the experimental spectrum of neomycin B. 30 references, 5 figures, 3 tables.
- Research Organization:
- Argonne National Lab., IL (USA)
- OSTI ID:
- 6757915
- Journal Information:
- J. Carbohydr. Chem.; (United States), Journal Name: J. Carbohydr. Chem.; (United States) Vol. 3:4; ISSN JCACD
- Country of Publication:
- United States
- Language:
- English
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