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1
Actinomycin synthesis in Streptomyces antibioticus: enzymatic conversion of 3-hydroxyanthranilic acid to 4-methyl-3-hydroxyanthranilic acid.抗生链霉菌中放线菌素的合成：3-羟基邻氨基苯甲酸向4-甲基-3-羟基邻氨基苯甲酸的酶促转化。
J Bacteriol. 1987 Dec;169(12):5575-8. doi: 10.1128/jb.169.12.5575-5578.1987.
2
Actinomycin synthesis in Streptomyces antibioticus. Purification and properties of a 3-hydroxyanthranilate 4-methyltransferase.
J Biol Chem. 1988 Apr 5;263(10):4602-6.
3
Control of the actinomycin biosynthetic pathway in and actinomycin resistance of Streptomyces spp.链霉菌属中放线菌素生物合成途径的调控及放线菌素抗性
J Bacteriol. 1982 May;150(2):598-603. doi: 10.1128/jb.150.2.598-603.1982.
4
4-Methyl-3-hydroxyanthranilic acid activating enzyme from actinomycin-producing Streptomyces chrysomallus.来自产放线菌素的金色链霉菌的4-甲基-3-羟基邻氨基苯甲酸激活酶。
Biochemistry. 1984 Mar 27;23(7):1479-84. doi: 10.1021/bi00302a022.
5
Biosynthesis of the actinomycin chromophore: incorporation of 3-hydroxy-4-methylanthranilic acid into actinomycins by Streptomyces antibioticus.放线菌素发色团的生物合成：3-羟基-4-甲基邻氨基苯甲酸被抗生链霉菌掺入放线菌素中。
J Bacteriol. 1969 Nov;100(2):977-84. doi: 10.1128/jb.100.2.977-984.1969.
6
Aromatic C-methyltransferases with antipodal stereoselectivity for structurally diverse phenolic amino acids catalyze the methylation step in the biosynthesis of the actinomycin chromophore.具有对结构多样的酚性氨基酸对映选择性的芳基 C-甲基转移酶催化放线菌素生色团生物合成中的甲基化步骤。
Biochemistry. 2010 Nov 16;49(45):9698-705. doi: 10.1021/bi101422r. Epub 2010 Oct 19.
7
Occurrence and biosynthesis of C-demethylactinomycins in actinomycin-producing Streptomyces chrysomallus and Streptomyces parvulus.金黄链霉菌和小单孢菌中产放线菌素过程中 C-去甲基放线菌素的产生和生物合成。
J Antibiot (Tokyo). 2013 Apr;66(4):211-8. doi: 10.1038/ja.2012.120. Epub 2013 Feb 20.
8
Phenoxazinone biosynthesis: accumulation of a precursor, 4-methyl-3-hydroxyanthranilic acid, by mutants of Streptomyces parvulus.吩恶嗪酮生物合成：小链霉菌突变体对前体4-甲基-3-羟基邻氨基苯甲酸的积累
J Gen Microbiol. 1979 Mar;111(1):121-32. doi: 10.1099/00221287-111-1-121.
9
Combined purification of actinomycin synthetase I and 3-hydroxyanthranilic acid 4-methyltransferase from Streptomyces antibioticus.从抗生链霉菌中联合纯化放线菌素合成酶I和3-羟基邻氨基苯甲酸4-甲基转移酶。
J Biol Chem. 1993 Apr 5;268(10):6831-4.
10
Enzymatic synthesis of actinomycin D and analogues containing N-methylalanine from synthetic pentapeptide lactone precursors.
J Antibiot (Tokyo). 1990 Jun;43(6):731-3. doi: 10.7164/antibiotics.43.731.

引用本文的文献

1
Discovery of actinomycin L, a new member of the actinomycin family of antibiotics.发现放线菌素 L，一种新型放线菌素类抗生素。
Sci Rep. 2022 Feb 18;12(1):2813. doi: 10.1038/s41598-022-06736-0.
2
The actinomycin biosynthetic gene cluster of Streptomyces chrysomallus: a genetic hall of mirrors for synthesis of a molecule with mirror symmetry.金霉素产生菌 Streptomyces chrysomallus 的放线菌素生物合成基因簇：一个具有分子镜面对称性的合成物的遗传之镜。
J Bacteriol. 2010 May;192(10):2583-95. doi: 10.1128/JB.01526-09. Epub 2010 Mar 19.
3
Nucleotide sequence, transcriptional analysis, and glucose regulation of the phenoxazinone synthase gene (phsA) from Streptomyces antibioticus.来自抗生链霉菌的吩恶嗪酮合酶基因（phsA）的核苷酸序列、转录分析及葡萄糖调控
J Bacteriol. 1995 Oct;177(20):5740-7. doi: 10.1128/jb.177.20.5740-5747.1995.
4
Metabolic regulation in Streptomyces parvulus during actinomycin D synthesis, studied with 13C- and 15N-labeled precursors by 13C and 15N nuclear magnetic resonance spectroscopy and by gas chromatography-mass spectrometry.利用13C和15N核磁共振光谱以及气相色谱-质谱联用技术，使用13C和15N标记的前体研究小链霉菌在放线菌素D合成过程中的代谢调控。
J Bacteriol. 1988 Sep;170(9):4055-64. doi: 10.1128/jb.170.9.4055-4064.1988.
5
Purification and characterization of S-adenosylhomocysteine deaminase from streptonigrin-producing Streptomyces flocculus.从产链黑菌素的絮状链霉菌中纯化及鉴定S-腺苷高半胱氨酸脱氨酶
J Bacteriol. 1989 Dec;171(12):6840-4. doi: 10.1128/jb.171.12.6840-6844.1989.
6
13C nuclear magnetic resonance and gas chromatography-mass spectrometry studies of carbon metabolism in the actinomycin D producer Streptomyces parvulus by use of 13C-labeled precursors.利用¹³C标记前体对放线菌素D产生菌小链霉菌碳代谢的¹³C核磁共振和气相色谱-质谱研究
J Bacteriol. 1991 Dec;173(24):7790-801. doi: 10.1128/jb.173.24.7790-7801.1991.

本文引用的文献

1
Biosynthesis of the actinomycin chromophore; enzymatic conversion of 4-methyl-3-hydroxyanthranilic acid to actinocin.放线菌素发色团的生物合成；4-甲基-3-羟基邻氨基苯甲酸向放线菌素的酶促转化。
J Biol Chem. 1962 Mar;237:882-6.
2
4-METHYL-3-HYDROXYANTHRANILIC ACID, AN INTERMEDIATE IN ACTINOMYCIN BIOSYNTHESIS.4-甲基-3-羟基邻氨基苯甲酸，放线菌素生物合成的中间体。
Biochem Biophys Res Commun. 1965 May 3;19:524-30. doi: 10.1016/0006-291x(65)90157-9.
3
Biosynthesis of the actinomycin chromophore. Studies with DL-[7alpha-14C] tryptophan and L-[Me-14C] methionine.放线菌素发色团的生物合成。用DL-[7α-14C]色氨酸和L-[甲基-14C]甲硫氨酸进行的研究。
Biochim Biophys Acta. 1962 Feb 26;57:283-9. doi: 10.1016/0006-3002(62)91121-6.
4
Incorporation of C14-labeled amino acids into actinomycin and protein by Streptomyces antibioticus.抗生素链霉菌将C14标记的氨基酸掺入放线菌素和蛋白质中。
J Biol Chem. 1963 Feb;238:666-75.
5
Phenoxazinone synthase from Streptomyces antibiotics: purification of the large and small enzyme forms.来自抗生素链霉菌的吩恶嗪酮合酶：大小两种酶形式的纯化
Arch Biochem Biophys. 1981 Oct 1;211(1):55-65. doi: 10.1016/0003-9861(81)90429-x.
6
Acyl pentapeptide lactone synthesis in actinomycin-producing streptomycetes by feeding with structural analogs of 4-methyl-3-hydroxyanthranilic acid.通过添加4-甲基-3-羟基邻氨基苯甲酸的结构类似物，在产放线菌素的链霉菌中合成酰基五肽内酯。
J Biol Chem. 1984 Jul 10;259(13):8226-31.
7
4-Methyl-3-hydroxyanthranilic acid activating enzyme from actinomycin-producing Streptomyces chrysomallus.来自产放线菌素的金色链霉菌的4-甲基-3-羟基邻氨基苯甲酸激活酶。
Biochemistry. 1984 Mar 27;23(7):1479-84. doi: 10.1021/bi00302a022.
8
Distinct kynureninase and hydroxykynureninase enzymes in an actinomycin-producing strain of Streptomyces parvulus.小链霉菌产放线菌素菌株中不同的犬尿氨酸酶和羟犬尿氨酸酶
Biochim Biophys Acta. 1980 Mar 14;612(1):97-106. doi: 10.1016/0005-2744(80)90282-x.
9
Activation of phenoxazinone synthase expression in Streptomyces lividans by cloned DNA sequences from Streptomyces antibioticus.来自抗生链霉菌的克隆DNA序列激活了淡紫链霉菌中苯噁嗪酮合酶的表达。
J Biol Chem. 1984 Nov 25;259(22):14158-64.
10
Molecular cloning and expression of the phenoxazinone synthase gene from Streptomyces antibioticus.抗生链霉菌中吩恶嗪酮合酶基因的分子克隆与表达
J Biol Chem. 1984 Nov 25;259(22):14151-7.

抗生链霉菌中放线菌素的合成：3-羟基邻氨基苯甲酸向4-甲基-3-羟基邻氨基苯甲酸的酶促转化。

Actinomycin synthesis in Streptomyces antibioticus: enzymatic conversion of 3-hydroxyanthranilic acid to 4-methyl-3-hydroxyanthranilic acid.

作者信息

Jones G H

机构信息

Department of Biology, University of Michigan, Ann Arbor 48109.

出版信息

J Bacteriol. 1987 Dec;169(12):5575-8. doi: 10.1128/jb.169.12.5575-5578.1987.

DOI:10.1128/jb.169.12.5575-5578.1987
PMID:2445729
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC213988/
Abstract

A methyltransferase which utilizes 3-hydroxyanthranilic acid (HAA) as a substrate was identified in detergent-treated extracts of the bacterium Streptomyces antibioticus. The enzyme catalyzes the transfer of methyl groups from [14C]S-adenosylmethionine to HAA, but does not catalyze the methylation of 3-hydroxy-DL-kynurenine. Enzyme, substrate, time, and pH dependencies for the methyl transfer reaction were examined. Reaction products obtained from scaled-up reaction mixtures were fractionated by chromatography on Dowex 1, and the Dowex 1 fractions were examined by paper and thin-layer chromatography. One Dowex fraction was shown to contain a radioactive product with the chromatographic properties of 4-methyl-3-hydroxyanthranilic acid (MHA), a known intermediate in the biosynthesis of actinomycin. Available evidence indicates that the conversion of HAA to MHA is an early step in the biosynthesis of actinomycin by S. antibioticus and other actinomycin-producing streptomycetes.

摘要

在经去污剂处理的抗生链霉菌提取物中鉴定出一种以3-羟基邻氨基苯甲酸（HAA）为底物的甲基转移酶。该酶催化甲基从[14C]S-腺苷甲硫氨酸转移至HAA，但不催化3-羟基-DL-犬尿氨酸的甲基化。研究了甲基转移反应的酶、底物、时间和pH依赖性。通过在Dowex 1上进行色谱分离对放大反应混合物得到的反应产物进行分馏，并通过纸色谱和薄层色谱对Dowex 1馏分进行检测。一个Dowex馏分显示含有一种具有4-甲基-3-羟基邻氨基苯甲酸（MHA）色谱特性的放射性产物，MHA是放线菌素生物合成中的一种已知中间体。现有证据表明，HAA向MHA的转化是抗生链霉菌和其他产生放线菌素的链霉菌合成放线菌素的早期步骤。