Biosynthesis of the Actinomycin Chromophore: Incorporation of 3-Hydroxy-4-Methylanthranilic Acid into Actinomycins by Streptomyces antibioticus
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| Published in | Journal of Bacteriology Vol. 100; no. 2; pp. 977 - 984 |
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| Main Authors | , , |
| Format | Journal Article |
| Language | English |
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American Society for Microbiology
01.11.1969
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| ISSN | 0021-9193 1067-8832 1098-5530 |
| DOI | 10.1128/JB.100.2.977-984.1969 |
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| AbstractList | Actinomycin synthesis by washed mycelia of Streptomyces antibioticus has been conducted in the presence of 3-hydroxy-4-methylanthranilate-(carboxyl-(14)C). Incorporation of this compound into actinomycins has been observed, which constitutes further evidence that 3-hydroxy-4-methylanthranilate is an intermediate in actinomycin biosynthesis. The position of the incorporated label has been determined to be within the actinomycin chromophore, and the label appears to be equally distributed between both halves of the chromophore. Incidental to these findings was the observation that the (14)C-labeled actinomycins were subject to rapid reabsorption by the organism with actinomycin V taken up preferentially to actinomycin IV.Actinomycin synthesis by washed mycelia of Streptomyces antibioticus has been conducted in the presence of 3-hydroxy-4-methylanthranilate-(carboxyl-(14)C). Incorporation of this compound into actinomycins has been observed, which constitutes further evidence that 3-hydroxy-4-methylanthranilate is an intermediate in actinomycin biosynthesis. The position of the incorporated label has been determined to be within the actinomycin chromophore, and the label appears to be equally distributed between both halves of the chromophore. Incidental to these findings was the observation that the (14)C-labeled actinomycins were subject to rapid reabsorption by the organism with actinomycin V taken up preferentially to actinomycin IV. Article Usage Stats Services JB Citing Articles Google Scholar PubMed Related Content Social Bookmarking CiteULike Delicious Digg Facebook Google+ Mendeley Reddit StumbleUpon Twitter current issue JB About JB Subscribers Authors Reviewers Advertisers Inquiries from the Press Permissions & Commercial Reprints ASM Journals Public Access Policy JB RSS Feeds 1752 N Street N.W. • Washington DC 20036 202.737.3600 • 202.942.9355 fax • journals@asmusa.org Print ISSN: 0021-9193 Online ISSN: 1098-5530 Copyright © 2014 by the American Society for Microbiology. For an alternate route to JB .asm.org, visit: JB Actinomycin synthesis by washed mycelia of Streptomyces antibioticus has been conducted in the presence of 3-hydroxy-4-methylanthranilate-(carboxyl-(14)C). Incorporation of this compound into actinomycins has been observed, which constitutes further evidence that 3-hydroxy-4-methylanthranilate is an intermediate in actinomycin biosynthesis. The position of the incorporated label has been determined to be within the actinomycin chromophore, and the label appears to be equally distributed between both halves of the chromophore. Incidental to these findings was the observation that the (14)C-labeled actinomycins were subject to rapid reabsorption by the organism with actinomycin V taken up preferentially to actinomycin IV. Actinomycin synthesis by washed mycelia of Streptomyces antibioticus has been conducted in the presence of 3-hydroxy-4-methylanthranilate-( carboxyl - 14 C). Incorporation of this compound into actinomycins has been observed, which constitutes further evidence that 3-hydroxy-4-methylanthranilate is an intermediate in actinomycin biosynthesis. The position of the incorporated label has been determined to be within the actinomycin chromophore, and the label appears to be equally distributed between both halves of the chromophore. Incidental to these findings was the observation that the 14 C-labeled actinomycins were subject to rapid reabsorption by the organism with actinomycin V taken up preferentially to actinomycin IV. |
| Author | Jonathan S. Nishimura Martha A. Ward Ellis E. Golub |
| AuthorAffiliation | a Department of Biochemistry, Tufts University School of Medicine, Boston, Massachusetts 02111 |
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| Author_xml | – sequence: 1 givenname: Ellis E. surname: Golub fullname: Golub, Ellis E. organization: Department of Biochemistry, Tufts University School of Medicine, Boston, Massachusetts 02111 – sequence: 2 givenname: Martha A. surname: Ward fullname: Ward, Martha A. organization: Department of Biochemistry, Tufts University School of Medicine, Boston, Massachusetts 02111 – sequence: 3 givenname: Jonathan S. surname: Nishimura fullname: Nishimura, Jonathan S. organization: Department of Biochemistry, Tufts University School of Medicine, Boston, Massachusetts 02111 |
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| Notes | ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 Present address: Department of Biochemistry, University of Texas Medical School, San Antonio, Tex. 78229. Present address: Division of Biology, California Institute of Technology, Pasadena, Calif. 91109. |
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| References_xml | – volume: 24 start-page: 513 year: 1966 ident: p_18 article-title: Microbial metabolism of actinomycins and other heterodetic antibiotic peptides publication-title: Biochem. Biophys. Res. Commun. doi: 10.1016/0006-291X(66)90349-4 – ident: p_3 doi: 10.1351/pac196102030405 – volume: 240 start-page: 4377 year: 1965 ident: p_24 article-title: Actinomycin synthesis in washed cells of Streptomyces antibioticus publication-title: J. Biol. Chem. doi: 10.1016/S0021-9258(18)97072-9 – volume: 1 start-page: 107 year: 1965 ident: p_9 article-title: Biosynthesis of highly labeled actinomycins publication-title: Mol. Pharmacol. – year: 1961 ident: p_22 article-title: Studies on the biosynthesis of actinomycin: enzymic synthesis of the phenoxazinone chromophore publication-title: J. Biol. 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Commun. doi: 10.1016/0006-291X(65)90157-9 – volume: 91 start-page: 1242 year: 1958 ident: p_4 article-title: Konstitution und Synthese des Actinomycin-Chromophors. XIX. Actinomycin. XL. Antibiotica aus publication-title: Actinomyceten. Chem. Ber. doi: 10.1002/cber.19580910621 – volume: 28 start-page: 665 year: 1967 ident: p_17 article-title: Evidence for the incorporation of L-thiazolidine-4-carboxylate into actinomycins by Streptomyces antibioticus publication-title: Biochem. Biophys. Res. Commun. doi: 10.1016/0006-291X(67)90366-X – volume: 126 start-page: 402 year: 1957 ident: p_10 article-title: Decomposition of actinomycin by a soil organism publication-title: Science doi: 10.1126/science.126.3270.402 – volume: 5 start-page: 95 year: 1957 ident: p_7 article-title: Actinomycin formation by Streptomyces cultures publication-title: Appl. 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Acta doi: 10.1016/0006-3002(62)91121-6 – reference: 13958485 - J Biol Chem. 1963 Feb;238:666-75 – reference: 14339002 - Biochem Biophys Res Commun. 1965 May 3;19:524-30 – reference: 4167872 - Biochem Biophys Res Commun. 1967 Sep 7;28(5):665-70 – reference: 4165264 - Biochem Biophys Res Commun. 1966 Aug 23;24(4):513-8 – reference: 13467219 - Science. 1957 Aug 30;126(3270):402-3 – reference: 13428781 - J Biol Chem. 1957 May;226(1):497-509 – reference: 13425525 - Appl Microbiol. 1957 Mar;5(2):95-102 – reference: 13784113 - J Biol Chem. 1961 Mar;236:PC16-8 – reference: 4158117 - Mol Pharmacol. 1965 Jul;1(1):107-9 – reference: 14039315 - Biochim Biophys Acta. 1962 Feb 26;57:283-9 – reference: 4171550 - J Biol Chem. 1968 Apr 25;243(8):1833-8 – reference: 14342335 - J Biol Chem. 1965 Jul;240:3071-8 – reference: 13559971 - Appl Microbiol. 1958 Jul;6(4):236-41 – reference: 4158638 - J Biol Chem. 1965 Nov;240(11):4377-81 – reference: 14454375 - J Biol Chem. 1962 Mar;237:882-6 |
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Mendeley... Actinomycin synthesis by washed mycelia of Streptomyces antibioticus has been conducted in the presence of 3-hydroxy-4-methylanthranilate-( carboxyl - 14 C).... Actinomycin synthesis by washed mycelia of Streptomyces antibioticus has been conducted in the presence of 3-hydroxy-4-methylanthranilate-(carboxyl-(14)C).... |
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| SubjectTerms | Carbon Isotopes Chromatography, Thin Layer Dactinomycin - biosynthesis Dactinomycin - isolation & purification Electrophoresis Hydrogen Peroxide - pharmacology Hydrogen-Ion Concentration Microbial Physiology and Metabolism ortho-Aminobenzoates - metabolism Streptomyces - metabolism Tryptophan - pharmacology Valine - metabolism |
| Title | Biosynthesis of the Actinomycin Chromophore: Incorporation of 3-Hydroxy-4-Methylanthranilic Acid into Actinomycins by Streptomyces antibioticus |
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