A natural combinatorial chemistry strategy in acylpolyamine toxins from Nephilinae orb-web spiders

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dc.contributor.authorPalma, Mario Sergio [UNESP]
dc.contributor.authorNakajima, T.
dc.contributor.institutionUniversidade Estadual Paulista (Unesp)
dc.contributor.institutionSuntory Inst Bioorgan Res
dc.date.accessioned2014-05-20T15:24:26Z
dc.date.available2014-05-20T15:24:26Z
dc.date.issued2005-01-01
dc.description.abstractThe present study shows how nature combined a small number of chemical building blocks to synthesize the acylpolyamine toxins in the venoms of Nephilinae orb-web spiders. Considering these structures in four parts, it was possible to rationalize a way to represent the natural combinatorial chemistry involved in the synthesis of these toxins: an aromatic moiety is connected through a linker amino acid to a polyamine chain, which in turn may be connected to an optional tail. The polyamine chains were classified into seven subtypes (from A to G) depending on the way the small chemical blocks are combined. These polyamine chains may be connected to one of the three possible chromophore moieties: 2,4-dihydroxyphenyl acetic acid, or 4-hydroxyindole acetic acid, or even with the indole acetic group. The connectivity between the aryl moiety and the polyamine chain is usually made through an asparagine residue; optionally a tail may be attached to the polyamine chain; nine different types of tails were identified among the 72 known acylpolyamine toxin structures. The combinations of three chromophores, two types of amino acid linkers, seven sub-types of polyamine backbone, and nine options of tails results in 378 different structural possibilities. However, we detected only 91 different toxin structures, which may represent the most successful structural trials in terms of efficiency of prey paralysis/death.en
dc.description.affiliationSão Paulo State Univ, Inst Biosci, Dept Biol, CEIS,Lab Struct Biol & Zoochem, BR-13506900 Rio Claro, SP, Brazil
dc.description.affiliationSuntory Inst Bioorgan Res, Osaka 618, Japan
dc.description.affiliationUnespSão Paulo State Univ, Inst Biosci, Dept Biol, CEIS,Lab Struct Biol & Zoochem, BR-13506900 Rio Claro, SP, Brazil
dc.format.extent209-234
dc.identifierhttp://dx.doi.org/10.1081/TXR-200057857
dc.identifier.citationToxin Reviews. Philadelphia: Taylor & Francis Inc., v. 24, n. 2, p. 209-234, 2005.
dc.identifier.doi10.1081/TXR-200057857
dc.identifier.issn0731-3837
dc.identifier.lattes2901888624506535
dc.identifier.urihttp://hdl.handle.net/11449/35046
dc.identifier.wosWOS:000230429300003
dc.language.isoeng
dc.publisherTaylor & Francis Inc
dc.relation.ispartofToxin Reviews
dc.rights.accessRightsAcesso restrito
dc.sourceWeb of Science
dc.subjectacylpolyamine toxinspt
dc.subjectorb-web spiderspt
dc.subjectspider toxinspt
dc.subjectcombinatorial chemistrypt
dc.titleA natural combinatorial chemistry strategy in acylpolyamine toxins from Nephilinae orb-web spidersen
dc.typeArtigo
dcterms.licensehttp://journalauthors.tandf.co.uk/permissions/reusingOwnWork.asp
dcterms.rightsHolderTaylor & Francis Inc
unesp.author.lattes2901888624506535
unesp.author.orcid0000-0002-7363-8211[1]
unesp.campusUniversidade Estadual Paulista (Unesp), Instituto de Biociências, Rio Claropt

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Artigos - Biologia - IBRC