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A tryptophan C-methyltransferase involved in streptonigrin biosynthesis in Streptomyces flocculus.一种参与絮状链霉菌中链黑菌素生物合成的色氨酸C-甲基转移酶。
Biochem J. 1984 May 15;220(1):309-13. doi: 10.1042/bj2200309.
2
Identification of (2S,3S)-β-Methyltryptophan as the Real Biosynthetic Intermediate of Antitumor Agent Streptonigrin.鉴定(2S,3S)-β-甲基色氨酸为抗肿瘤药物链黑菌素真正的生物合成中间体。
Sci Rep. 2016 Feb 5;6:20273. doi: 10.1038/srep20273.
3
Demonstration of a metabolic grid at an early step in the streptonigrin biosynthetic pathway in Streptomyces flocculus.在絮凝链霉菌中链黑菌素生物合成途径早期步骤中代谢网格的证明。
J Antibiot (Tokyo). 1984 Feb;37(2):159-66. doi: 10.7164/antibiotics.37.159.
4
Formation of 2-methyltryptophan in the biosynthesis of thiostrepton: isolation of S-adenosylmethionine:tryptophan 2-methyltransferase.硫链丝菌素生物合成中2-甲基色氨酸的形成：S-腺苷甲硫氨酸：色氨酸2-甲基转移酶的分离
Arch Biochem Biophys. 1990 Apr;278(1):35-40. doi: 10.1016/0003-9861(90)90227-p.
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.
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The mechanisms of radical SAM/cobalamin methylations: an evolving working hypothesis.自由基 SAM/钴胺甲基化的机制：一个不断发展的工作假说。
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7
Tryptophan C-methyltransferase of Streptomyces flocculus.絮凝链霉菌的色氨酸C-甲基转移酶
Methods Enzymol. 1987;142:235-42. doi: 10.1016/s0076-6879(87)42032-6.
8
Characterization of streptonigrin biosynthesis reveals a cryptic carboxyl methylation and an unusual oxidative cleavage of a N-C bond.斯特雷酮霉素生物合成的特征揭示了一种隐藏的羧基甲基化和一种不寻常的 N-C 键氧化裂解。
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9
Ammonium effects on streptonigrin biosynthesis by Streptomyces flocculus.铵对絮状链霉菌生物合成链黑菌素的影响。
J Ind Microbiol. 1990 Sep;6(1):43-8. doi: 10.1007/BF01576175.
10
Isolation and characterization of tryptophan transaminase and indolepyruvate C-methyltransferase. Enzymes involved in indolmycin biosynthesis in Streptomyces griseus.色氨酸转氨酶和吲哚丙酮酸C-甲基转移酶的分离与鉴定。参与灰色链霉菌中吲哚霉素生物合成的酶。
J Biol Chem. 1975 Oct 10;250(19):7819-25.

引用本文的文献

1
Xantholipin B produced by the stnR inactivation mutant Streptomyces flocculus CGMCC 4.1223 WJN-1.由stnR失活突变体弗氏链霉菌CGMCC 4.1223 WJN-1产生的黄脂素B。
J Antibiot (Tokyo). 2017 Jan;70(1):90-95. doi: 10.1038/ja.2016.60. Epub 2016 Jun 22.
2
Identification of (2S,3S)-β-Methyltryptophan as the Real Biosynthetic Intermediate of Antitumor Agent Streptonigrin.鉴定(2S,3S)-β-甲基色氨酸为抗肿瘤药物链黑菌素真正的生物合成中间体。
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Purification and characterization of Streptomyces griseus catechol O-methyltransferase.灰色链霉菌儿茶酚O-甲基转移酶的纯化与特性分析
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4
S-adenosylhomocysteine metabolism in Streptomyces flocculus.絮凝链霉菌中S-腺苷同型半胱氨酸的代谢
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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
Ammonium effects on streptonigrin biosynthesis by Streptomyces flocculus.铵对絮状链霉菌生物合成链黑菌素的影响。
J Ind Microbiol. 1990 Sep;6(1):43-8. doi: 10.1007/BF01576175.

本文引用的文献

1
Streptonigrin, an antitumor substance. I. Isolation and characterization.链黑菌素，一种抗肿瘤物质。I. 分离与特性鉴定。
Antibiot Annu. 1959;7:950-3.
2
L-lysine epsilon-aminotransferase involved in cephamycin C synthesis in Streptomyces lactamdurans.参与内酰胺链霉菌中头孢霉素C合成的L-赖氨酸ε-氨基转移酶。
Antimicrob Agents Chemother. 1980 Apr;17(4):679-85. doi: 10.1128/AAC.17.4.679.
3
Biosynthesis of indoleisopropionic acid by Claviceps. Biological C-methylation involving an intact methyl group.麦角菌合成吲哚丙酸。涉及完整甲基的生物C-甲基化。
Arch Biochem Biophys. 1969 May;131(2):430-40. doi: 10.1016/0003-9861(69)90415-9.
4
The structure of telomycin.端粒霉素的结构。
J Am Chem Soc. 1968 Jan 17;90(2):462-70. doi: 10.1021/ja01004a043.
5
[Spectrophotometric method for the determination of the content of bruneomycin in culture fluid and solutions].[分光光度法测定培养液和溶液中布鲁诺霉素的含量]
Antibiotiki. 1971 Jan;16(1):44-6.
6
Streptonigrin biosynthesis. I. Origin of the 4-phenylpicolinic acid moiety.链黑菌素的生物合成。I. 4-苯基吡啶甲酸部分的起源。
J Am Chem Soc. 1977 Aug 3;99(16):5496-7. doi: 10.1021/ja00458a052.
7
Isolation and characterization of tryptophan transaminase and indolepyruvate C-methyltransferase. Enzymes involved in indolmycin biosynthesis in Streptomyces griseus.色氨酸转氨酶和吲哚丙酮酸C-甲基转移酶的分离与鉴定。参与灰色链霉菌中吲哚霉素生物合成的酶。
J Biol Chem. 1975 Oct 10;250(19):7819-25.
8
Studies of nitrogen metabolism using 13C NMR spectroscopy. 1. Streptonigrin biosynthesis.利用13C核磁共振光谱法对氮代谢的研究。1. 链黑菌素的生物合成。
J Am Chem Soc. 1978 Mar 1;100(5):1624-6. doi: 10.1021/ja00473a061.
9
Effect of primary metabolites on secondary metabolism.初级代谢产物对次级代谢的影响。
Annu Rev Microbiol. 1977;31:343-56. doi: 10.1146/annurev.mi.31.100177.002015.

一种参与絮状链霉菌中链黑菌素生物合成的色氨酸C-甲基转移酶。

A tryptophan C-methyltransferase involved in streptonigrin biosynthesis in Streptomyces flocculus.

作者信息

Hartley D L, Speedie M K

出版信息

Biochem J. 1984 May 15;220(1):309-13. doi: 10.1042/bj2200309.

DOI:10.1042/bj2200309
PMID:6743267
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC1153624/
Abstract

A C-methyltransferase that catalyses the transfer of a methyl group from S-adenosylmethionine to C-3 of tryptophan, resulting in beta-methyltryptophan, has been identified in cell-free extracts of streptonigrin-producing Streptomyces flocculus. The absolute configuration of the product was shown to be (2S,3R)-beta-methyltryptophan by high-pressure liquid chromatography and reactivity with D- and L-amino acid oxidases. In shake culture, maximum specific activity occurs after S. flocculus enters stationary phase, but before significant streptonigrin accumulates.

摘要

在产链黑菌素的絮状链霉菌的无细胞提取物中，已鉴定出一种C-甲基转移酶，该酶催化将甲基从S-腺苷甲硫氨酸转移至色氨酸的C-3位，生成β-甲基色氨酸。通过高压液相色谱以及与D-和L-氨基酸氧化酶的反应，证明产物的绝对构型为(2S,3R)-β-甲基色氨酸。在摇瓶培养中，最大比活性在絮状链霉菌进入稳定期后、但在链黑菌素大量积累之前出现。