STRUCTURE OF ANTIMYCIN-A COMPLEX

STRUCTURE OF ANTIMYCIN-A COMPLEX
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DOI:
10.1039/jr9610000889
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发表时间:
1961-01-01
期刊:
JOURNAL OF THE CHEMICAL SOCIETY
影响因子:
--
通讯作者:
RICKARDS, RW
RICKARDS, RW
中科院分区:
其他
文献类型:
--
作者:
BIRCH, AJ;HARADA, Y;RICKARDS, RW

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抗霉素-A的温和碱性水解形成的中性片段在1788和1748 cm-1处显示红外吸收(在CS中)。1与货车Tamelen、Strong和Quarcklo基于模型化合物的反应和进一步碱水解成酸的混合物(其主要成分是(+)-α-甲基丁酸和未鉴定的酮酸Cl 1H 2,O 3)提出的β-酰氧基-γ-内酯结构(如111)相容。Blastmycinone是基本上由抗霉素-A组成的Blastmycin的相应降解产物,Yonehara和Takeuchi根据降解证据将其表述为(111; R= nC,H,R '= CH,* CHMe,),而在完成本工作后,纯化的抗霉素-A的中性片段仅在R= nC,H,方面有所不同。中性片段的气相色谱法解决了至少两个组件,证实了早期的证据的不均匀性,并表明负责抗霉素-A复合物的不同组分的结构变化驻留在这部分的分子。将内酯混合物(111)剧烈碱性水解,得到酮酸级分(IV),通过反相色谱法纯化。
The neutral fragment formed on mild alkaline hydrolysis of antimycin-A showed infrared absorption (in CS,) at 1788 and 1748 crn.-l compatible with the P-acyloxy-y-lactone structure (as in 111) proposed by van Tamelen, Strong, and Quarcklo on the basis of reactjons of model compounds and further alkaline hydrolysis to a mixture of acids whose major components were (+)-a-methylbutyric acid and an unidentified keto-acid, CllH2, O3. Blastmycinone, the corresponding degradation product of blastmycin which consists essentially of antimycin-A,, was formulated by Yonehara and Takeuchi as (111; R= nC, H,, R'= CH,* CHMe,) on degradative evidence, while, after completion of the present work, the neutral fragment from purified antimycin-A, was shown14 to differ only in having R= nC, H,,. Vapour-phase chromatography of the neutral fragment resolved at least two components, confirming the earlier evidence of inhomogeneity and indicating that the structural variations responsible for the different components of the antimycin-A complex resided in this portion of the molecule. Vigorous alkaline hydrolysis of the lactonic ester mixture (111) afforded a keto-acid fraction (IV), purified through the