STUDIES ON POLYOXINS, ANTIFUNGAL ANTIBIOTICS .13. STRUCTURE OF POLYOXINS
STUDIES ON POLYOXINS, ANTIFUNGAL ANTIBIOTICS .13. STRUCTURE OF POLYOXINS
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DOI：
10.1021/ja01054a045
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发表时间：
1969-01-01
影响因子：
15
通讯作者：
SUZUKI, S
中科院分区：
文献类型：
--
作者：
ISONO, K;ASAHI, K;SUZUKI, S
发现多氧菌素AL是一类新的肽核苷，其结构如方案I所示。多抗霉素水解后得到三组特殊的L-氨基酸，即1-（5 ′-氨基-5 ′-脱氧-β-D-异呋喃糖基）-5-羟甲基尿嘧啶（多抗霉素C）或其三个核碱基类似物，5-O-氨甲酰基-2-氨基-2-脱氧-L-木糖酸或其3-脱氧类似物，3-亚乙基-L-氮杂环丁烷-2-羧酸。这些结构是根据化学和光谱学证据确定的。所有多氧霉素共有的5 '-氨基呋喃糖苷构成具有α-氨基酸性质的核苷。序列分析表明，多氧菌素是这些部分的二肽或三肽。所阐明的结构体现了多抗霉素的所有有趣的化学特征。本文还讨论了该结构的生化意义。
Polyoxins AL were found to be a new class of peptide nucleosides having the structures shown in Scheme I. Hydrolytic degradation of polyoxins afforded three groups of unusual-L-amino acids, ie, l-(5'-amino-5'-deoxy-jS-D-allofuranuronosyl)-5-hydroxymethyluracil (polyoxin C) or its three nucleobase analogs, 5-0-carbamoyl-2-amino-2-deoxy-L-xylonic acid or its 3-deoxy analog, and 3-ethylidene-L-azetidine-2-carboxylic acid. These structures were established on chemical and spectroscopic evidence. 5'-Aminofuranuronoside common to all polyoxins constitutes a nucleoside with a-amino acid nature. Sequence analysis showed polyoxins are di-or tripeptide of these moieties. The structures so elucidated embody all the interesting chemical features of polyoxins. The hypothetical biochemical significance of the structure was also discussed.