Viriplanin A, a new anthracycline antibiotic of the nogalamycin group. II. The structure of a novel hydroxyamino sugar from reduced viriplanin A.
Methyl 2,3,6-trideoxy-3-hydroxyamino-3-C-methyl-alpha-D-ribo-hexopyranoside+ ++ (2) and the corresponding amino sugar (4) were isolated from reduced viriplanin A by acidic methanolysis and esterified to the di-p-bromobenzoates (3 and 5), respectively. The absolute configuration of crystalline 3 was determined by X-ray analysis to be alpha-D. This result could be confirmed by oxidation of 2 to methyl alpha-D-decilonitroside (6) and from the CD spectra of 3 and 5. Thus, the nitrogen-containing sugars of viriplanin A and probably those of decilorubicin and arugomycin belong to the D-series.
Kind
R
R
Institut für Organische Chemie, Universität Göttingen, FRG.
Hütter
K
K
Zeeck
A
A
Schmidt-Bäse
K
K
Egert
E
E
D018943:Anthracyclines; D000903:Antibiotics, Antineoplastic; D055598:Chemical Phenomena; D002621:Chemistry; D002942:Circular Dichroism; D008968:Molecular Conformation; D010084:Oxidation-Reduction
D018943:Anthracyclines; D000903:Antibiotics, Antineoplastic; C050239:viriplanin A