7-α-甲氧基头孢菌素的生物合成。分子氧的掺入。
Biosynthesis of a 7-alpha-methoxycephalosporin. Incorporation of molecular oxygen.
作者信息
O'Sullivan J, Aplin R T, Stevens C M, Abraham E P
出版信息
Biochem J. 1979 Apr 1;179(1):47-52. doi: 10.1042/bj1790047.
Abstract
A 7-alpha-methoxycephalosporin containing a carbamoyloxymethyl substituent at C-3 (cephamycin C) has been isolated from the extracellular fluid of an aqueous suspension of Streptomyces clavuligerus shaken in the presence of 18O2. The cephalosporin has been converted into its N-acetyl dimethyl ester and the distribution of 18O in the latter determined by chemical-ionization mass spectrometry. The results indicate that the oxygen atom of the methoxy group, as well as that linked to the exocyclic methylene group at C-3, is derived from molecular O2.
摘要
从在(^{18}O_2)存在下振荡的棒状链霉菌水悬浮液的细胞外液中分离出一种在C-3位含有氨甲酰氧基甲基取代基的7-α-甲氧基头孢菌素（头霉素C）。该头孢菌素已转化为其N-乙酰二甲基酯，并通过化学电离质谱法测定了后者中(^{18}O)的分布。结果表明，甲氧基的氧原子以及与C-3位环外亚甲基相连的氧原子均来源于分子氧(O_2)。
相似文献
1
Biosynthesis of a 7-alpha-methoxycephalosporin. Incorporation of molecular oxygen.7-α-甲氧基头孢菌素的生物合成。分子氧的掺入。
Biochem J. 1979 Apr 1;179(1):47-52. doi: 10.1042/bj1790047.
2
The conversion of cephalosporins to 7 alpha-methoxycephalosporins by cell-free extracts of Streptomyces clavuligerus.棒状链霉菌无细胞提取物将头孢菌素转化为7α-甲氧基头孢菌素。
Biochem J. 1980 Feb 15;186(2):613-6. doi: 10.1042/bj1860613.
3
Holomycin and N-propionylholothin, antibiotics produced by a cephamycin C producer.氯霉素和N-丙酰卤霉素，由头霉素C产生菌产生的抗生素。
J Antibiot (Tokyo). 1977 Apr;30(4):334-6. doi: 10.7164/antibiotics.30.334.
4
Oganomycin A, a new cephamycin-type antibiotic produced by Streptomyces oganonensis and its derivatives, oganomycins B, GA and GB.
J Antibiot (Tokyo). 1981 Nov;34(11):1507-12. doi: 10.7164/antibiotics.34.1507.
5
Oganomycins, new 7-methoxy-cephalosporins produced by precursor fermentation with heterocyclic thiols.奥加霉素，通过与杂环硫醇进行前体发酵产生的新型7-甲氧基头孢菌素。
J Antibiot (Tokyo). 1980 Sep;33(9):1074-8. doi: 10.7164/antibiotics.33.1074.
6
Regulation of cephamycin C synthesis, aspartokinase, dihydrodipicolinic acid synthetase, and homoserine dehydrogenase by aspartic acid family amino acids in Streptomyces clavuligerus.棒状链霉菌中天冬氨酸家族氨基酸对头孢霉素C合成、天冬氨酸激酶、二氢吡啶二羧酸合成酶和高丝氨酸脱氢酶的调控
Antimicrob Agents Chemother. 1982 Jan;21(1):74-84. doi: 10.1128/AAC.21.1.74.
7
[New producer of cephamycin C, Streptomyces filipinensis var. cephamycini var. nov].
Antibiotiki. 1976 Dec;21(12):1059-62.
8
Production of the cephalosporate C-2 by a Streptomyces lactamdurans mutant defective in cephamycin C biosynthesis.
J Antibiot (Tokyo). 1984 Jun;37(6):664-6. doi: 10.7164/antibiotics.37.664.
9
Solid state fermentation for cephalosporin production by Streptomyces clavuligerus and Cephalosporium acremonium.棒状链霉菌和顶头孢霉固态发酵生产头孢菌素
Experientia. 1989 Dec 1;45(11-12):1061-5. doi: 10.1007/BF01950159.
10
Cystathionine gamma-lyase activity in the cephamycin C producer Streptomyces lactamdurans.
J Antibiot (Tokyo). 1981 May;34(5):583-9. doi: 10.7164/antibiotics.34.583.
引用本文的文献
1
Roles of 2-oxoglutarate oxygenases and isopenicillin N synthase in β-lactam biosynthesis.2-氧代戊二酸氧酶和异青霉素 N 合酶在β-内酰胺生物合成中的作用。
Nat Prod Rep. 2018 Aug 15;35(8):735-756. doi: 10.1039/c8np00002f.
2
Production of clavulanic acid and cephamycin C by Streptomyces clavuligerus in palm-oil medium.棕榈油培养基中棒状链霉菌生产克拉维酸和头孢菌素 C。
World J Microbiol Biotechnol. 1996 Jan;12(1):73-5. doi: 10.1007/BF00327805.
3
Induction of holomycin production and complex metabolic changes by the argR mutation in Streptomyces clavuligerus NP1.链霉菌 NP1 的 argR 突变诱导霍洛霉素的产生和复杂的代谢变化。
Appl Environ Microbiol. 2012 May;78(9):3431-41. doi: 10.1128/AEM.07699-11. Epub 2012 Feb 17.
4
pcd mutants of Streptomyces clavuligerus still produce cephamycin C.棒状链霉菌的pcd突变体仍能产生头霉素C。
J Bacteriol. 2007 Aug;189(16):5867-74. doi: 10.1128/JB.00712-07. Epub 2007 Jun 15.
5
Genes for beta-lactam antibiotic biosynthesis.β-内酰胺抗生素生物合成相关基因。
Antonie Van Leeuwenhoek. 1995;67(2):181-200. doi: 10.1007/BF00871213.
6
A two-protein component 7 alpha-cephem-methoxylase encoded by two genes of the cephamycin C cluster converts cephalosporin C to 7-methoxycephalosporin C.由头霉素C基因簇的两个基因编码的一种双蛋白组分7α-头孢烯甲氧基化酶将头孢菌素C转化为7-甲氧基头孢菌素C。
J Bacteriol. 1995 Apr;177(8):2230-5. doi: 10.1128/jb.177.8.2230-2235.1995.
7
The conversion of cephalosporins to 7 alpha-methoxycephalosporins by cell-free extracts of Streptomyces clavuligerus.棒状链霉菌无细胞提取物将头孢菌素转化为7α-甲氧基头孢菌素。
Biochem J. 1980 Feb 15;186(2):613-6. doi: 10.1042/bj1860613.
8
Biosynthesis of monobactam compounds: origin of the carbon atoms in the beta-lactam ring.单环β-内酰胺类化合物的生物合成：β-内酰胺环中碳原子的来源
Antimicrob Agents Chemother. 1982 Apr;21(4):558-64. doi: 10.1128/AAC.21.4.558.
9
Purification of isopenicillin N synthetase.异青霉素N合成酶的纯化
Biochem J. 1984 Sep 15;222(3):789-95. doi: 10.1042/bj2220789.
本文引用的文献
1
Colorimetric detection of penicillins and cephalosporins on paper.纸上比色法检测青霉素和头孢菌素
Nature. 1961 Sep 16;191:1161-3. doi: 10.1038/1911161a0.
2
Biosynthesis of penicillin N and cephalosporin C. Antibiotic production and other features of the metabolism of Cephalosporium sp.青霉素N和头孢菌素C的生物合成。头孢霉属的抗生素生产及代谢的其他特征
Biochem J. 1967 Jun;103(3):877-90. doi: 10.1042/bj1030877.
3
Beta-lactam antibiotics from Streptomyces.来自链霉菌的β-内酰胺类抗生素。
J Am Chem Soc. 1971 May 5;93(9):2308-10. doi: 10.1021/ja00738a035.
4
Incorporation of labeled precursors into A16886B, a novel -lactam antibiotic produced by Streptomyces clavuligerus.将标记前体掺入A16886B中，A16886B是由棒状链霉菌产生的一种新型β-内酰胺抗生素。
Antimicrob Agents Chemother. 1972 Mar;1(3):247-51. doi: 10.1128/AAC.1.3.247.
5
Letter: The occurrence of deacetoxycephalosporin C in fungi and streptomycetes.信函：脱乙酰氧基头孢菌素C在真菌和链霉菌中的出现。
J Antibiot (Tokyo). 1974 Apr;27(4):298-300. doi: 10.7164/antibiotics.27.298.
6
Nocardicin A, a new monocyclic beta-lactam antibiotic. I. Discovery, isolation and characterization.诺卡菌素A，一种新型单环β-内酰胺抗生素。I. 发现、分离与特性鉴定。
J Antibiot (Tokyo). 1976 May;29(5):492-500. doi: 10.7164/antibiotics.29.492.
7
Naturally-occurring beta-lactamase inhibitors with antibacterial activity.
J Antibiot (Tokyo). 1976 Jun;29(6):668-9. doi: 10.7164/antibiotics.29.668.
8
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.
9
Chemical-ionization mass spectrometry of beta-lactam antibiotics.β-内酰胺类抗生素的化学电离质谱分析
J Antibiot (Tokyo). 1975 Sep;28(9):668-75. doi: 10.7164/antibiotics.28.668.
10
The oxygenation of the 3-methyl group of 7beta-(5-D-aminoadipamido)-3-methylceph-3-em-4-carboxylic acid (desacetoxycephalosporin C) by extracts of Acremonium chrysogenum [proceedings].产黄顶头孢霉提取物对7β-(5-D-氨基己酰胺基)-3-甲基头孢-3-烯-4-羧酸（去乙酰氧基头孢菌素C）的3-甲基进行的氧化反应[会议论文集]
Biochem Soc Trans. 1977;5(4):1024-6. doi: 10.1042/bst0051024.
Zotero 插件