维里普拉宁A，诺加霉素类的一种新型蒽环类抗生素。II. 还原型维里普拉宁A中一种新型羟基氨基糖的结构。

Viriplanin A, a new anthracycline antibiotic of the nogalamycin group. II. The structure of a novel hydroxyamino sugar from reduced viriplanin A.

作者信息

Kind R, Hütter K, Zeeck A, Schmidt-Bäse K, Egert E

机构信息

Institut für Organische Chemie, Universität Göttingen, FRG.

出版信息

J Antibiot (Tokyo). 1989 Jan;42(1):7-13. doi: 10.7164/antibiotics.42.7.

DOI:10.7164/antibiotics.42.7

PMID:2921229

Abstract

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.

摘要

通过酸性甲醇解从还原型病毒菌素A中分离出2,3,6-三脱氧-3-羟基氨基-3-C-甲基-α-D-核糖己吡喃糖苷++ +（2）和相应的氨基糖（4），并分别酯化得到二对溴苯甲酸酯（3和5）。通过X射线分析确定结晶3的绝对构型为α-D。该结果可通过将2氧化为α-D-去氧糖腈苷（6）以及3和5的圆二色光谱得到证实。因此，病毒菌素A的含氮糖以及可能的柔红霉素和阿柔比星的含氮糖都属于D-系列。