Structure of fuscopeptins, phytotoxic metabolites of Pseudomonas fuscovaginae
The structure of the fuscopeptins, bioactive lipodepsipeptides produced in culture by the gramineae pathogen Pseudomonas fuscovaginae, has been determined. The combined use of FAB mass spectrometry, NMR spectroscopy and chemical and enzymatic procedures allowed one to define a peptide moiety corresp...
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| Veröffentlicht in: | FEBS letters 1996-03, Vol.381 (3), p.213-216 |
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| creator | Ballio, A. Bossa, F. Camoni, L. Di Giorgio, D. Flamand, M.-C. Maraite, H. Nitti, G. Pucci, P. Scaloni, A. |
| description | The structure of the fuscopeptins, bioactive lipodepsipeptides produced in culture by the gramineae pathogen
Pseudomonas fuscovaginae, has been determined. The combined use of FAB mass spectrometry, NMR spectroscopy and chemical and enzymatic procedures allowed one to define a peptide moiety corresponding to ZDhb-DPro-LLeu-DAla-DAla-DAla-DAlaDVal-Gly-DAla-DVal-DAla-DVal-ZDhb-DaThr-LAla-LDabDDab-LPhe with the terminal carboxyl group closing a macrocyclic ring on the hydroxyl group of the
allothreonine residue. The N-terminus is in turn acylated by 3-hydroxyoctanoate in fuscopeptin A and 3-hydroxydecanoate in fuscopeptin B. Some preliminary data on the biological activity of fuscopeptins are also reported. |
| doi_str_mv | 10.1016/0014-5793(96)00043-9 |
| format | Article |
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Pseudomonas fuscovaginae, has been determined. The combined use of FAB mass spectrometry, NMR spectroscopy and chemical and enzymatic procedures allowed one to define a peptide moiety corresponding to ZDhb-DPro-LLeu-DAla-DAla-DAla-DAlaDVal-Gly-DAla-DVal-DAla-DVal-ZDhb-DaThr-LAla-LDabDDab-LPhe with the terminal carboxyl group closing a macrocyclic ring on the hydroxyl group of the
allothreonine residue. The N-terminus is in turn acylated by 3-hydroxyoctanoate in fuscopeptin A and 3-hydroxydecanoate in fuscopeptin B. Some preliminary data on the biological activity of fuscopeptins are also reported.</description><identifier>ISSN: 0014-5793</identifier><identifier>EISSN: 1873-3468</identifier><identifier>DOI: 10.1016/0014-5793(96)00043-9</identifier><identifier>PMID: 8601458</identifier><language>eng</language><publisher>England: Elsevier B.V</publisher><subject>Amino Acid Sequence ; aThr, allothreonine ; Bacterial Proteins - pharmacology ; Bacterial Toxins - chemistry ; Bacterial Toxins - isolation & purification ; Bacterial Toxins - pharmacology ; Dab, 2,4-diaminobutyric acid ; Dhb, 2,3-dehydro-2-aminobutyric acid ; FAB-MS, fast atom bombardment mass spectrometry ; FP, fuscopeptin ; Fungi - drug effects ; Fuscopeptins ; GC-MS, gas chromatography mass spectrometry ; Lipodepsipeptides ; Magnetic Resonance Spectroscopy ; Microbial Sensitivity Tests ; Molecular Sequence Data ; Peptides, Cyclic - chemistry ; Peptides, Cyclic - isolation & purification ; Peptides, Cyclic - pharmacology ; Phytotoxins ; Plant Diseases - microbiology ; Pseudomonas - metabolism ; Pseudomonas fuscovaginae ; SP, syringopeptin ; Spectrometry, Mass, Fast Atom Bombardment ; SR, syringomycin ; Structure-Activity Relationship ; TBDMS, t-butyldimethylsilyl ; TFA, trifluoroacetic acid</subject><ispartof>FEBS letters, 1996-03, Vol.381 (3), p.213-216</ispartof><rights>1996</rights><rights>FEBS Letters 381 (1996) 1873-3468 © 2015 Federation of European Biochemical Societies</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c5329-71a328ea582d3f99ace49d766743fd778fd8b96168af680003bea26f774f38bf3</citedby><cites>FETCH-LOGICAL-c5329-71a328ea582d3f99ace49d766743fd778fd8b96168af680003bea26f774f38bf3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1016%2F0014-5793%2896%2900043-9$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/0014579396000439$$EHTML$$P50$$Gelsevier$$Hfree_for_read</linktohtml><link.rule.ids>314,776,780,1411,3537,27901,27902,45550,45551,65306</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/8601458$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Ballio, A.</creatorcontrib><creatorcontrib>Bossa, F.</creatorcontrib><creatorcontrib>Camoni, L.</creatorcontrib><creatorcontrib>Di Giorgio, D.</creatorcontrib><creatorcontrib>Flamand, M.-C.</creatorcontrib><creatorcontrib>Maraite, H.</creatorcontrib><creatorcontrib>Nitti, G.</creatorcontrib><creatorcontrib>Pucci, P.</creatorcontrib><creatorcontrib>Scaloni, A.</creatorcontrib><title>Structure of fuscopeptins, phytotoxic metabolites of Pseudomonas fuscovaginae</title><title>FEBS letters</title><addtitle>FEBS Lett</addtitle><description>The structure of the fuscopeptins, bioactive lipodepsipeptides produced in culture by the gramineae pathogen
Pseudomonas fuscovaginae, has been determined. The combined use of FAB mass spectrometry, NMR spectroscopy and chemical and enzymatic procedures allowed one to define a peptide moiety corresponding to ZDhb-DPro-LLeu-DAla-DAla-DAla-DAlaDVal-Gly-DAla-DVal-DAla-DVal-ZDhb-DaThr-LAla-LDabDDab-LPhe with the terminal carboxyl group closing a macrocyclic ring on the hydroxyl group of the
allothreonine residue. The N-terminus is in turn acylated by 3-hydroxyoctanoate in fuscopeptin A and 3-hydroxydecanoate in fuscopeptin B. Some preliminary data on the biological activity of fuscopeptins are also reported.</description><subject>Amino Acid Sequence</subject><subject>aThr, allothreonine</subject><subject>Bacterial Proteins - pharmacology</subject><subject>Bacterial Toxins - chemistry</subject><subject>Bacterial Toxins - isolation & purification</subject><subject>Bacterial Toxins - pharmacology</subject><subject>Dab, 2,4-diaminobutyric acid</subject><subject>Dhb, 2,3-dehydro-2-aminobutyric acid</subject><subject>FAB-MS, fast atom bombardment mass spectrometry</subject><subject>FP, fuscopeptin</subject><subject>Fungi - drug effects</subject><subject>Fuscopeptins</subject><subject>GC-MS, gas chromatography mass spectrometry</subject><subject>Lipodepsipeptides</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Microbial Sensitivity Tests</subject><subject>Molecular Sequence Data</subject><subject>Peptides, Cyclic - chemistry</subject><subject>Peptides, Cyclic - isolation & purification</subject><subject>Peptides, Cyclic - pharmacology</subject><subject>Phytotoxins</subject><subject>Plant Diseases - microbiology</subject><subject>Pseudomonas - metabolism</subject><subject>Pseudomonas fuscovaginae</subject><subject>SP, syringopeptin</subject><subject>Spectrometry, Mass, Fast Atom Bombardment</subject><subject>SR, syringomycin</subject><subject>Structure-Activity Relationship</subject><subject>TBDMS, t-butyldimethylsilyl</subject><subject>TFA, trifluoroacetic acid</subject><issn>0014-5793</issn><issn>1873-3468</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1996</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqNkMtKxDAUhoMoOl7eQGFWomC1aTq5bAQVRwVFQV2HND3RSNvUJFXn7W3t4FJchZz_cg4fQrs4PcYppidpivNkxgQ5EPQwTdOcJGIFTTBnJCE55ato8mvZQJshvPUmzLFYR-uc9sqMT9DdY_Sdjp2HqTNT0wXtWmijbcLRtH1dRBfdl9XTGqIqXGUjhMH3EKArXe0aFcbMh3qxjYJttGZUFWBn-W6h5_nl08V1cnt_dXNxdpvoGclEwrAiGQc141lJjBBKQy5KRinLiSkZ46bkhaCYcmUo768mBaiMGsZyQ3hhyBbaH3tb7947CFHWNmioKtWA64JkTNCM51lvzEej9i4ED0a23tbKLyRO5UBRDojkgEiK4dNTlKKP7S37u6KG8je0xNbr81H_tBUs_tUp55fn2SAMc0F_psOi07EIelofFrwM2kKjobQedJSls39f-g0e_pU9</recordid><startdate>19960304</startdate><enddate>19960304</enddate><creator>Ballio, A.</creator><creator>Bossa, F.</creator><creator>Camoni, L.</creator><creator>Di Giorgio, D.</creator><creator>Flamand, M.-C.</creator><creator>Maraite, H.</creator><creator>Nitti, G.</creator><creator>Pucci, P.</creator><creator>Scaloni, A.</creator><general>Elsevier B.V</general><scope>6I.</scope><scope>AAFTH</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>19960304</creationdate><title>Structure of fuscopeptins, phytotoxic metabolites of Pseudomonas fuscovaginae</title><author>Ballio, A. ; Bossa, F. ; Camoni, L. ; Di Giorgio, D. ; Flamand, M.-C. ; Maraite, H. ; Nitti, G. ; Pucci, P. ; Scaloni, A.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c5329-71a328ea582d3f99ace49d766743fd778fd8b96168af680003bea26f774f38bf3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1996</creationdate><topic>Amino Acid Sequence</topic><topic>aThr, allothreonine</topic><topic>Bacterial Proteins - pharmacology</topic><topic>Bacterial Toxins - chemistry</topic><topic>Bacterial Toxins - isolation & purification</topic><topic>Bacterial Toxins - pharmacology</topic><topic>Dab, 2,4-diaminobutyric acid</topic><topic>Dhb, 2,3-dehydro-2-aminobutyric acid</topic><topic>FAB-MS, fast atom bombardment mass spectrometry</topic><topic>FP, fuscopeptin</topic><topic>Fungi - drug effects</topic><topic>Fuscopeptins</topic><topic>GC-MS, gas chromatography mass spectrometry</topic><topic>Lipodepsipeptides</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Microbial Sensitivity Tests</topic><topic>Molecular Sequence Data</topic><topic>Peptides, Cyclic - chemistry</topic><topic>Peptides, Cyclic - isolation & purification</topic><topic>Peptides, Cyclic - pharmacology</topic><topic>Phytotoxins</topic><topic>Plant Diseases - microbiology</topic><topic>Pseudomonas - metabolism</topic><topic>Pseudomonas fuscovaginae</topic><topic>SP, syringopeptin</topic><topic>Spectrometry, Mass, Fast Atom Bombardment</topic><topic>SR, syringomycin</topic><topic>Structure-Activity Relationship</topic><topic>TBDMS, t-butyldimethylsilyl</topic><topic>TFA, trifluoroacetic acid</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ballio, A.</creatorcontrib><creatorcontrib>Bossa, F.</creatorcontrib><creatorcontrib>Camoni, L.</creatorcontrib><creatorcontrib>Di Giorgio, D.</creatorcontrib><creatorcontrib>Flamand, M.-C.</creatorcontrib><creatorcontrib>Maraite, H.</creatorcontrib><creatorcontrib>Nitti, G.</creatorcontrib><creatorcontrib>Pucci, P.</creatorcontrib><creatorcontrib>Scaloni, A.</creatorcontrib><collection>ScienceDirect Open Access Titles</collection><collection>Elsevier:ScienceDirect:Open Access</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>FEBS letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Ballio, A.</au><au>Bossa, F.</au><au>Camoni, L.</au><au>Di Giorgio, D.</au><au>Flamand, M.-C.</au><au>Maraite, H.</au><au>Nitti, G.</au><au>Pucci, P.</au><au>Scaloni, A.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Structure of fuscopeptins, phytotoxic metabolites of Pseudomonas fuscovaginae</atitle><jtitle>FEBS letters</jtitle><addtitle>FEBS Lett</addtitle><date>1996-03-04</date><risdate>1996</risdate><volume>381</volume><issue>3</issue><spage>213</spage><epage>216</epage><pages>213-216</pages><issn>0014-5793</issn><eissn>1873-3468</eissn><abstract>The structure of the fuscopeptins, bioactive lipodepsipeptides produced in culture by the gramineae pathogen
Pseudomonas fuscovaginae, has been determined. The combined use of FAB mass spectrometry, NMR spectroscopy and chemical and enzymatic procedures allowed one to define a peptide moiety corresponding to ZDhb-DPro-LLeu-DAla-DAla-DAla-DAlaDVal-Gly-DAla-DVal-DAla-DVal-ZDhb-DaThr-LAla-LDabDDab-LPhe with the terminal carboxyl group closing a macrocyclic ring on the hydroxyl group of the
allothreonine residue. The N-terminus is in turn acylated by 3-hydroxyoctanoate in fuscopeptin A and 3-hydroxydecanoate in fuscopeptin B. Some preliminary data on the biological activity of fuscopeptins are also reported.</abstract><cop>England</cop><pub>Elsevier B.V</pub><pmid>8601458</pmid><doi>10.1016/0014-5793(96)00043-9</doi><tpages>4</tpages><oa>free_for_read</oa></addata></record> |
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| identifier | ISSN: 0014-5793 |
| ispartof | FEBS letters, 1996-03, Vol.381 (3), p.213-216 |
| issn | 0014-5793 1873-3468 |
| language | eng |
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| source | Wiley Online Library - AutoHoldings Journals; MEDLINE; Elsevier ScienceDirect Journals; EZB-FREE-00999 freely available EZB journals; Alma/SFX Local Collection |
| subjects | Amino Acid Sequence aThr, allothreonine Bacterial Proteins - pharmacology Bacterial Toxins - chemistry Bacterial Toxins - isolation & purification Bacterial Toxins - pharmacology Dab, 2,4-diaminobutyric acid Dhb, 2,3-dehydro-2-aminobutyric acid FAB-MS, fast atom bombardment mass spectrometry FP, fuscopeptin Fungi - drug effects Fuscopeptins GC-MS, gas chromatography mass spectrometry Lipodepsipeptides Magnetic Resonance Spectroscopy Microbial Sensitivity Tests Molecular Sequence Data Peptides, Cyclic - chemistry Peptides, Cyclic - isolation & purification Peptides, Cyclic - pharmacology Phytotoxins Plant Diseases - microbiology Pseudomonas - metabolism Pseudomonas fuscovaginae SP, syringopeptin Spectrometry, Mass, Fast Atom Bombardment SR, syringomycin Structure-Activity Relationship TBDMS, t-butyldimethylsilyl TFA, trifluoroacetic acid |
| title | Structure of fuscopeptins, phytotoxic metabolites of Pseudomonas fuscovaginae |
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