Himastatin, a New Antitumor Antibiotic from Streptomyces hygroscopicus: III. Structural Elucidation
The structure of the antitumor antibiotic himastatin was determined using a combination of spectroscopic and chemical degradation techniques. Himastatin is a unique dimeric cyclohexadepsipeptide joined through a biphenyl linkage between two oxidized tryptophan units. The gross structure of the dimer...
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Veröffentlicht in: | Journal of antibiotics 1996/03/25, Vol.49(3), pp.299-311 |
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container_title | Journal of antibiotics |
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creator | LEET, JOHN E. SCHROEDER, DANIEL R. GOLIK, JERZY MATSON, JAMES A. DOYLE, TERRENCE W. LAM, KIN S. HILL, SUSAN E. LEE, MIKE S. WHITNEY, JEFFREY L. KRISHNAN, BALA S. |
description | The structure of the antitumor antibiotic himastatin was determined using a combination of spectroscopic and chemical degradation techniques. Himastatin is a unique dimeric cyclohexadepsipeptide joined through a biphenyl linkage between two oxidized tryptophan units. The gross structure of the dimer was established through degradative ozonolysis. Himastatin consists of D-valine, D-threonine, L-leucine, L-α-hydroxyisovaleric acid, (3R, 5R)-5-hydroxypiperazic acid, and (2R, 3aR, 8aR)-3a-hydroxyhexahydropyrrolo[2, 3b]indole 2-carboxylic acid subunits. |
doi_str_mv | 10.7164/antibiotics.49.299 |
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Himastatin consists of D-valine, D-threonine, L-leucine, L-α-hydroxyisovaleric acid, (3R, 5R)-5-hydroxypiperazic acid, and (2R, 3aR, 8aR)-3a-hydroxyhexahydropyrrolo[2, 3b]indole 2-carboxylic acid subunits.</description><identifier>ISSN: 0021-8820</identifier><identifier>EISSN: 1881-1469</identifier><identifier>DOI: 10.7164/antibiotics.49.299</identifier><identifier>PMID: 8626248</identifier><identifier>CODEN: JANTAJ</identifier><language>eng</language><publisher>Tokyo: JAPAN ANTIBIOTICS RESEARCH ASSOCIATION</publisher><subject>Amino Acid Sequence ; Animals ; Antibiotics, Antineoplastic - biosynthesis ; Antibiotics, Antineoplastic - chemistry ; Antibiotics, Antineoplastic - pharmacology ; Antineoplastic agents ; Biological and medical sciences ; Chemotherapy ; Humans ; Magnetic Resonance Spectroscopy ; Medical sciences ; Molecular Sequence Data ; Molecular Structure ; Peptides, Cyclic - biosynthesis ; Peptides, Cyclic - chemistry ; Peptides, Cyclic - pharmacology ; Pharmacology. Drug treatments ; Spectrometry, Mass, Fast Atom Bombardment ; Spectrophotometry, Ultraviolet ; Stereoisomerism ; Streptomyces - metabolism ; Tumor Cells, Cultured</subject><ispartof>The Journal of Antibiotics, 1996/03/25, Vol.49(3), pp.299-311</ispartof><rights>Japan Antibiotics Research Association</rights><rights>1996 INIST-CNRS</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3839-618ba8369f1f20cc4974bba6ac1907d1e68e44432b01c8bd53dc2dae9abcad6d3</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,1883,27924,27925</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=3071761$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/8626248$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>LEET, JOHN E.</creatorcontrib><creatorcontrib>SCHROEDER, DANIEL R.</creatorcontrib><creatorcontrib>GOLIK, JERZY</creatorcontrib><creatorcontrib>MATSON, JAMES A.</creatorcontrib><creatorcontrib>DOYLE, TERRENCE W.</creatorcontrib><creatorcontrib>LAM, KIN S.</creatorcontrib><creatorcontrib>HILL, SUSAN E.</creatorcontrib><creatorcontrib>LEE, MIKE S.</creatorcontrib><creatorcontrib>WHITNEY, JEFFREY L.</creatorcontrib><creatorcontrib>KRISHNAN, BALA S.</creatorcontrib><title>Himastatin, a New Antitumor Antibiotic from Streptomyces hygroscopicus: III. Structural Elucidation</title><title>Journal of antibiotics</title><addtitle>J. Antibiot.</addtitle><description>The structure of the antitumor antibiotic himastatin was determined using a combination of spectroscopic and chemical degradation techniques. Himastatin is a unique dimeric cyclohexadepsipeptide joined through a biphenyl linkage between two oxidized tryptophan units. The gross structure of the dimer was established through degradative ozonolysis. Himastatin consists of D-valine, D-threonine, L-leucine, L-α-hydroxyisovaleric acid, (3R, 5R)-5-hydroxypiperazic acid, and (2R, 3aR, 8aR)-3a-hydroxyhexahydropyrrolo[2, 3b]indole 2-carboxylic acid subunits.</description><subject>Amino Acid Sequence</subject><subject>Animals</subject><subject>Antibiotics, Antineoplastic - biosynthesis</subject><subject>Antibiotics, Antineoplastic - chemistry</subject><subject>Antibiotics, Antineoplastic - pharmacology</subject><subject>Antineoplastic agents</subject><subject>Biological and medical sciences</subject><subject>Chemotherapy</subject><subject>Humans</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Medical sciences</subject><subject>Molecular Sequence Data</subject><subject>Molecular Structure</subject><subject>Peptides, Cyclic - biosynthesis</subject><subject>Peptides, Cyclic - chemistry</subject><subject>Peptides, Cyclic - pharmacology</subject><subject>Pharmacology. Drug treatments</subject><subject>Spectrometry, Mass, Fast Atom Bombardment</subject><subject>Spectrophotometry, Ultraviolet</subject><subject>Stereoisomerism</subject><subject>Streptomyces - metabolism</subject><subject>Tumor Cells, Cultured</subject><issn>0021-8820</issn><issn>1881-1469</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1996</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpNkEtLAzEUhYMotVb_gCDMQlw5Na9mkmUp1opFF-o63Mlk2inzqMkM0n9v6pTSTRI43z3n5iB0S_A4IYI_Qd0WadG0hfFjrsZUqTM0JFKSmHChztEQY0piKSm-RFfebzBmCUvkAA2koIJyOUTzRVGBb6Et6scIonf7G02Da9tVjft_9f5R7poq-myd3bZNtTPWR-vdyjXeNNvCdP4aXeRQentzuEfoe_78NVvEy4-X19l0GRsmmYoFkSlIJlROcoqN4SrhaQoCDFE4yYgV0nLOGU0xMTLNJiwzNAOrIDWQiYyN0EPvu3XNT2d9q6vCG1uWUNum8zqRmOAJpgGkPWjCkt7ZXG9d-KnbaYL1vjx9Up7mSofywtDdwb1LK5sdRw5tBf3-oIM3UOYOalP4I8ZwQhJBAvbWY5tQ7MoedXAhrLSnyUQJuU9n_RGWOFJmDU7bmv0BnsuXVQ</recordid><startdate>19960325</startdate><enddate>19960325</enddate><creator>LEET, JOHN E.</creator><creator>SCHROEDER, DANIEL R.</creator><creator>GOLIK, JERZY</creator><creator>MATSON, JAMES A.</creator><creator>DOYLE, TERRENCE W.</creator><creator>LAM, KIN S.</creator><creator>HILL, SUSAN E.</creator><creator>LEE, MIKE S.</creator><creator>WHITNEY, JEFFREY L.</creator><creator>KRISHNAN, BALA S.</creator><general>JAPAN ANTIBIOTICS RESEARCH ASSOCIATION</general><general>Japan Antibiotics Research Association</general><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>19960325</creationdate><title>Himastatin, a New Antitumor Antibiotic from Streptomyces hygroscopicus</title><author>LEET, JOHN E. ; SCHROEDER, DANIEL R. ; GOLIK, JERZY ; MATSON, JAMES A. ; DOYLE, TERRENCE W. ; LAM, KIN S. ; HILL, SUSAN E. ; LEE, MIKE S. ; WHITNEY, JEFFREY L. ; KRISHNAN, BALA S.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3839-618ba8369f1f20cc4974bba6ac1907d1e68e44432b01c8bd53dc2dae9abcad6d3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1996</creationdate><topic>Amino Acid Sequence</topic><topic>Animals</topic><topic>Antibiotics, Antineoplastic - biosynthesis</topic><topic>Antibiotics, Antineoplastic - chemistry</topic><topic>Antibiotics, Antineoplastic - pharmacology</topic><topic>Antineoplastic agents</topic><topic>Biological and medical sciences</topic><topic>Chemotherapy</topic><topic>Humans</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Medical sciences</topic><topic>Molecular Sequence Data</topic><topic>Molecular Structure</topic><topic>Peptides, Cyclic - biosynthesis</topic><topic>Peptides, Cyclic - chemistry</topic><topic>Peptides, Cyclic - pharmacology</topic><topic>Pharmacology. Drug treatments</topic><topic>Spectrometry, Mass, Fast Atom Bombardment</topic><topic>Spectrophotometry, Ultraviolet</topic><topic>Stereoisomerism</topic><topic>Streptomyces - metabolism</topic><topic>Tumor Cells, Cultured</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>LEET, JOHN E.</creatorcontrib><creatorcontrib>SCHROEDER, DANIEL R.</creatorcontrib><creatorcontrib>GOLIK, JERZY</creatorcontrib><creatorcontrib>MATSON, JAMES A.</creatorcontrib><creatorcontrib>DOYLE, TERRENCE W.</creatorcontrib><creatorcontrib>LAM, KIN S.</creatorcontrib><creatorcontrib>HILL, SUSAN E.</creatorcontrib><creatorcontrib>LEE, MIKE S.</creatorcontrib><creatorcontrib>WHITNEY, JEFFREY L.</creatorcontrib><creatorcontrib>KRISHNAN, BALA S.</creatorcontrib><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of antibiotics</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>LEET, JOHN E.</au><au>SCHROEDER, DANIEL R.</au><au>GOLIK, JERZY</au><au>MATSON, JAMES A.</au><au>DOYLE, TERRENCE W.</au><au>LAM, KIN S.</au><au>HILL, SUSAN E.</au><au>LEE, MIKE S.</au><au>WHITNEY, JEFFREY L.</au><au>KRISHNAN, BALA S.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Himastatin, a New Antitumor Antibiotic from Streptomyces hygroscopicus: III. Structural Elucidation</atitle><jtitle>Journal of antibiotics</jtitle><addtitle>J. Antibiot.</addtitle><date>1996-03-25</date><risdate>1996</risdate><volume>49</volume><issue>3</issue><spage>299</spage><epage>311</epage><pages>299-311</pages><issn>0021-8820</issn><eissn>1881-1469</eissn><coden>JANTAJ</coden><abstract>The structure of the antitumor antibiotic himastatin was determined using a combination of spectroscopic and chemical degradation techniques. Himastatin is a unique dimeric cyclohexadepsipeptide joined through a biphenyl linkage between two oxidized tryptophan units. The gross structure of the dimer was established through degradative ozonolysis. Himastatin consists of D-valine, D-threonine, L-leucine, L-α-hydroxyisovaleric acid, (3R, 5R)-5-hydroxypiperazic acid, and (2R, 3aR, 8aR)-3a-hydroxyhexahydropyrrolo[2, 3b]indole 2-carboxylic acid subunits.</abstract><cop>Tokyo</cop><pub>JAPAN ANTIBIOTICS RESEARCH ASSOCIATION</pub><pmid>8626248</pmid><doi>10.7164/antibiotics.49.299</doi><tpages>13</tpages><oa>free_for_read</oa></addata></record> |
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subjects | Amino Acid Sequence Animals Antibiotics, Antineoplastic - biosynthesis Antibiotics, Antineoplastic - chemistry Antibiotics, Antineoplastic - pharmacology Antineoplastic agents Biological and medical sciences Chemotherapy Humans Magnetic Resonance Spectroscopy Medical sciences Molecular Sequence Data Molecular Structure Peptides, Cyclic - biosynthesis Peptides, Cyclic - chemistry Peptides, Cyclic - pharmacology Pharmacology. Drug treatments Spectrometry, Mass, Fast Atom Bombardment Spectrophotometry, Ultraviolet Stereoisomerism Streptomyces - metabolism Tumor Cells, Cultured |
title | Himastatin, a New Antitumor Antibiotic from Streptomyces hygroscopicus: III. Structural Elucidation |
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