Biosynthesis of Antibiotics of the Virginiamycin Family, 2. Assignment of the 13C-NMR Spectra of Virginiamycin M1 and Antibiotic A2315A
Biosynthesis of Antibiotics of the Virginiamycin Family, 2. Assignment of the 13C-NMR Spectra of Virginiamycin M1 and Antibiotic A2315A
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DOI：
10.1021/np50028a008
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发表时间：
1983-07
影响因子：
5.1
通讯作者：
J. W. Lefevre;T. Glass;M. Kolpak;D. Kingston;Paul N. Chen
中科院分区：
文献类型：
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作者：
J. W. Lefevre;T. Glass;M. Kolpak;D. Kingston;Paul N. Chen
作为使用13C标记前体进行生物合成研究的一部分，分析了抗生素维吉尼亚霉素和A2315A的13C-核磁共振波谱。通过对[L，2-13C2]乙酸酯和L-[U-‘3C3]-丝氨酸生物合成抗生素的碳-碳偶联反应，以及与模型化合物的比较，确定了信号的归属。维吉尼亚霉素(1)是一种来源于多种不同来源微生物的多不饱和环肽内酯类抗生素。它被不同地命名为米卡霉素A、平链霉素A、原始霉素IIA、链霉素A、PA 114Al和维甲霉素A(1)，但维吉尼亚霉素Mj被认为是具有优先权的名称(2)。其结构通过化学和光谱技术相结合(3，4)进行了鉴定，并通过X-射线晶体结构进行了确认(5)。抗生素A2315A(2)与维吉尼亚霉素Mj的不同之处在于存在D-丙氨酸单元而不是后者的脱氢脯氨酸单元，以及C-16氧功能(6)的氧化水平。
As part of a biosynthetic study using 13C-labeled precursors, the 13C-nmr spectra of the antibioticsvirginiamycin and A2315A have been analyzed. Signal assign-ments were based on specific proton decoupling, chemical shift and multiplicity analysis, car-bon-carbon couplings of antibiotic biosynthesized from [l, 2-13C2] acetate and L-[U-'3C3]-serine, and comparison with model compounds.Virginiamycin(1) is a polyunsaturated cyclic peptolide antibiotic obtained from a number of different source microorganisms. It has variously been named as mikamycin A, ostreogrycin A, pristinamycin IIA, streptogramin A, PA 114 Al, and vernamycin A (1), but the name virginiamycin Mj has been accepted as the one having precedence (2). Its structure was elucidated by a combination of chemical and spectroscopic techniques (3, 4), and has been confirmed by an X-ray crystal structure(5). The antibiotic A2315A (2) differs from virginiamycin Mj in the presence of a D-alanine unit in place of the dehydroproline unit of the latter and in the oxidation level of the C-16 oxygen function (6).