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结构和立体化学甲基脯氨酸异构体对放线菌素生物合成的影响。

Effect of structural and stereochemical methylproline isomers on actinomycin biosynthesis.

作者信息

Yoshida T, Mauger A, Weissbach H, Katz E

出版信息

J Bacteriol. 1968 Mar;95(3):952-8. doi: 10.1128/jb.95.3.952-958.1968.

DOI:10.1128/jb.95.3.952-958.1968
PMID:4171116
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC252115/
Abstract

The inhibitory effect of methylprolines on actinomycin biosynthesis by Streptomyces antibioticus was studied; the order of effectiveness was 3- >4- >5-methyl-dl-proline. Cis-3-methyl-dl-proline was 14 times more active than the trans isomer. It was also found that 4- and, possibly, 5-methylproline were incorporated into the actinomycin molecule. When 4-methylproline was present, three new actinomycins, representing 50 to 60% of the antibiotic mixture, were synthesized. Growth of the organism may be stimulated at concentrations (0.1 to 1.0 mug per ml) of 3-methylproline that inhibit antibiotic formation, thus providing additional evidence for a different mechanism of actinomycin synthesis from that of protein synthesis. Azetidine-2-carboxylic acid, piperdine-2-carboxylic acid, and hydroxyproline (but not sarcosine) reversed the inhibition due to 3-methylproline.

摘要

研究了甲基脯氨酸对产抗生素链霉菌合成放线菌素的抑制作用;其有效性顺序为3->4->5-甲基-dl-脯氨酸。顺式-3-甲基-dl-脯氨酸的活性比反式异构体高14倍。还发现4-甲基脯氨酸以及可能的5-甲基脯氨酸被掺入放线菌素分子中。当存在4-甲基脯氨酸时,合成了三种新的放线菌素,占抗生素混合物的50%至60%。在抑制抗生素形成的3-甲基脯氨酸浓度(每毫升0.1至1.0微克)下,生物体的生长可能会受到刺激,从而为放线菌素合成与蛋白质合成机制不同提供了额外证据。氮杂环丁烷-2-羧酸、哌啶-2-羧酸和羟脯氨酸(但不包括肌氨酸)可逆转3-甲基脯氨酸引起的抑制作用。

相似文献

1
Effect of structural and stereochemical methylproline isomers on actinomycin biosynthesis.结构和立体化学甲基脯氨酸异构体对放线菌素生物合成的影响。
J Bacteriol. 1968 Mar;95(3):952-8. doi: 10.1128/jb.95.3.952-958.1968.
2
Differential effects of cis-3-methylproline and trans-3-methylproline on actinomycin synthesis in Streptomyces antibioticus.顺式-3-甲基脯氨酸和反式-3-甲基脯氨酸对抗生链霉菌中放线菌素合成的不同影响。
J Biol Chem. 1968 Apr 25;243(8):1833-8.
3
Novel actinomycins formed by biosynthetic incorporation of cis- and trans-4-methylproline.通过顺式和反式-4-甲基脯氨酸的生物合成掺入形成的新型放线菌素。
Antimicrob Agents Chemother. 1977 Jun;11(6):1056-63. doi: 10.1128/AAC.11.6.1056.
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Influence of methylproline isomers upon actinomycin biosynthesis.
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Origin of the sarcosine molecules of actinomycins.放线菌素中肌氨酸分子的起源。
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Production, isolation, and properties of azetomycins.氮杂霉素的制备、分离及性质
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Actinomycin biosynthesis by protoplasts derived from Streptomyces parvulus.由小链霉菌原生质体合成放线菌素
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Actinomycin analogues containing pipecolic acid: relationship of structure to biological activity.含哌啶酸的放线菌素类似物:结构与生物活性的关系。
J Bacteriol. 1968 Jun;95(6):2139-50. doi: 10.1128/jb.95.6.2139-2150.1968.
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[New actinomycin from Actinomyces sp. No. 2].[来自放线菌属2号菌株的新型放线菌素]
Antibiotiki. 1981 Jan;26(1):5-7.

引用本文的文献

1
Preparation of four new antibiotics from a mutant of Streptomyces fradiae.从弗氏链霉菌突变体中制备四种新型抗生素。
Proc Natl Acad Sci U S A. 1969 May;63(1):198-204. doi: 10.1073/pnas.63.1.198.
2
Novel actinomycins formed by biosynthetic incorporation of cis- and trans-4-methylproline.通过顺式和反式-4-甲基脯氨酸的生物合成掺入形成的新型放线菌素。
Antimicrob Agents Chemother. 1977 Jun;11(6):1056-63. doi: 10.1128/AAC.11.6.1056.

本文引用的文献

1
SEPARATION OF THE BIOSYNTHESIS OF THE ANTIBIOTIC POLYPEPTIDE TYROCIDINE FROM PROTEIN BIOSYNTHESIS.抗生素多肽短杆菌酪肽的生物合成与蛋白质生物合成的分离
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Effect of chloromycetin and penicillin on the incorporation of amino acids into actinomycin and protein by Streptomyces antibioticus.氯霉素和青霉素对抗生素链霉菌将氨基酸掺入放线菌素和蛋白质中的影响。
Biochem Biophys Res Commun. 1962 Jul 3;8:186-90. doi: 10.1016/0006-291x(62)90260-7.
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THE SELECTIVE PHOTOREDUCTION OF URIDINE IN POLYNUCLEOTIDES.多核苷酸中尿苷的选择性光还原
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THE BIOSYNTHESIS OF POLYMYXIN B BY GROWING CULTURES OF BACILLUS POLYMYXA.多粘芽孢杆菌培养物生长过程中多粘菌素B的生物合成
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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.
10
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。
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