将δ-（L-α-氨基（4,5-³H）己二酰基）-L-半胱氨酰-D-（4,4-³H）缬氨酸中的³H掺入异青霉素N。
Incorporation of 3H from delta-(L-alpha-amino (4,5-3H)adipyl)-L-cysteinyl-D-(4,4-3H)valine into isopenicillin N.
作者信息
O'Sullivan J, Bleaney R C, Huddleston J A, Abraham E P
出版信息
Biochem J. 1979 Nov 15;184(2):421-6. doi: 10.1042/bj1840421.
Abstract
- delta-(L-alpha-Amino[4,5-3H]adipyl)-L-cysteinyl-D-[4,4-3H]valine has been synthesized from its constituent amino acids, the L-alpha-amino[4,5-3H]adipic acid being obtained by reduction with 3H2 of methyl 5-acetamido-5,5-diethoxycarbonylpent-2-enoate and subsequent decarboxylation and hydrolysis. 2. In a cell-free system prepared by lysis of protoplasts of Cephalosporium acremonium 3H was incorporated from the doubly labelled tripeptide into a compound that behaved like penicillin N or isopenicillin N. The relative specific radioactivities of the alpha-aminoadipyl and penicillamine moieties of the penicillin were the same (within experimental error) as those of the alpha-aminoadipic acid and valine residues respectively of the tripeptide. 3. The behaviour of the labelled alpha-aminoadipic acid from the penicillin to the L-amino acid oxidase of Crotalus adamanteus venom showed that it was mainly L-alpha-aminoadipic acid. 4. The results are consistent with the hypothesis that the carbon skeleton of the LLD-tripeptide is incorporated intact into the penicillin molecule and that the first product is isopenicillin N.
摘要
- δ-（L-α-氨基[4,5-³H]己二酰基）-L-半胱氨酰-D-[4,4-³H]缬氨酸已由其组成氨基酸合成，L-α-氨基[4,5-³H]己二酸是通过用³H₂还原5-乙酰氨基-5,5-二乙氧基羰基戊-2-烯酸甲酯，随后脱羧和水解得到的。2. 在通过裂解顶头孢霉原生质体制备的无细胞体系中 [³H] 从双标记的三肽掺入到一种表现得像青霉素N或异青霉素N的化合物中。青霉素的α-氨基己二酰基和青霉素胺部分的相对比放射性分别与三肽的α-氨基己二酸和缬氨酸残基的相对比放射性相同（在实验误差范围内）。3. 来自青霉素的标记α-氨基己二酸对金刚背响尾蛇毒的L-氨基酸氧化酶的作用表明它主要是L-α-氨基己二酸。4. 结果与以下假设一致：LLD-三肽的碳骨架完整地掺入青霉素分子中，并且第一个产物是异青霉素N。
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Formation and properties of protoplasts from antibiotic-producing strains of Penicillium chrysogenum and Cephalosporium acremonium.产抗生素的产黄青霉和顶头孢霉原生质体的形成及特性
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Quantitative film detection of 3H and 14C in polyacrylamide gels by fluorography.通过荧光自显影对聚丙烯酰胺凝胶中的³H和¹⁴C进行定量胶片检测。
Eur J Biochem. 1975 Aug 15;56(2):335-41. doi: 10.1111/j.1432-1033.1975.tb02238.x.
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Synthesis of delta-(alpha-aminoadipyl)cysteinylvaline and its role in penicillin biosynthesis.δ-（α-氨基己二酰）半胱氨酰缬氨酸的合成及其在青霉素生物合成中的作用。
Biochem J. 1976 Sep 1;157(3):651-60. doi: 10.1042/bj1570651.
10
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