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...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Journal of antibiotics 1996/03/25, Vol.49(3), pp.299-311
Hauptverfasser: 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.
Format: Artikel
Sprache:eng
Schlagworte:
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 311
container_issue 3
container_start_page 299
container_title Journal of antibiotics
container_volume 49
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
format Article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_78010502</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>78010502</sourcerecordid><originalsourceid>FETCH-LOGICAL-c3839-618ba8369f1f20cc4974bba6ac1907d1e68e44432b01c8bd53dc2dae9abcad6d3</originalsourceid><addsrcrecordid>eNpNkEtLAzEUhYMotVb_gCDMQlw5Na9mkmUp1opFF-o63Mlk2inzqMkM0n9v6pTSTRI43z3n5iB0S_A4IYI_Qd0WadG0hfFjrsZUqTM0JFKSmHChztEQY0piKSm-RFfebzBmCUvkAA2koIJyOUTzRVGBb6Et6scIonf7G02Da9tVjft_9f5R7poq-myd3bZNtTPWR-vdyjXeNNvCdP4aXeRQentzuEfoe_78NVvEy4-X19l0GRsmmYoFkSlIJlROcoqN4SrhaQoCDFE4yYgV0nLOGU0xMTLNJiwzNAOrIDWQiYyN0EPvu3XNT2d9q6vCG1uWUNum8zqRmOAJpgGkPWjCkt7ZXG9d-KnbaYL1vjx9Up7mSofywtDdwb1LK5sdRw5tBf3-oIM3UOYOalP4I8ZwQhJBAvbWY5tQ7MoedXAhrLSnyUQJuU9n_RGWOFJmDU7bmv0BnsuXVQ</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>78010502</pqid></control><display><type>article</type><title>Himastatin, a New Antitumor Antibiotic from Streptomyces hygroscopicus: III. Structural Elucidation</title><source>MEDLINE</source><source>J-STAGE</source><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.</creator><creatorcontrib>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.</creatorcontrib><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><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&amp;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>
fulltext fulltext
identifier ISSN: 0021-8820
ispartof The Journal of Antibiotics, 1996/03/25, Vol.49(3), pp.299-311
issn 0021-8820
1881-1469
language eng
recordid cdi_proquest_miscellaneous_78010502
source MEDLINE; J-STAGE
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
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-03T15%3A33%3A05IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Himastatin,%20a%20New%20Antitumor%20Antibiotic%20from%20Streptomyces%20hygroscopicus:%20III.%20Structural%20Elucidation&rft.jtitle=Journal%20of%20antibiotics&rft.au=LEET,%20JOHN%20E.&rft.date=1996-03-25&rft.volume=49&rft.issue=3&rft.spage=299&rft.epage=311&rft.pages=299-311&rft.issn=0021-8820&rft.eissn=1881-1469&rft.coden=JANTAJ&rft_id=info:doi/10.7164/antibiotics.49.299&rft_dat=%3Cproquest_cross%3E78010502%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=78010502&rft_id=info:pmid/8626248&rfr_iscdi=true