MersV1, PubMed, Curation, bibRecord, 002402

Solid-phase synthesis of DOTA-peptides.

Identifieur interne : 002402 ( PubMed/Curation ); précédent : 002401; suivant : 002403

Solid-phase synthesis of DOTA-peptides.

Auteurs : Luis M. De Le N-Rodriguez [États-Unis] ; Zoltan Kovacs ; Gregg R. Dieckmann ; A Dean Sherry

Source :

Chemistry (Weinheim an der Bergstrasse, Germany) [ 0947-6539 ] ; 2004.

RBID : pubmed:15007806

Descripteurs français

KwdFr :
- Acides aminés (synthèse chimique), Composés hétéromonocycliques (), Fluorènes (synthèse chimique), Gadolinium (), Ligands, Peptides (synthèse chimique), Structure moléculaire, Structures macromoléculaires.
MESH :
- synthèse chimique : Acides aminés, Fluorènes, Peptides.
- Composés hétéromonocycliques, Gadolinium, Ligands, Structure moléculaire, Structures macromoléculaires.

English descriptors

KwdEn :
- Amino Acids (chemical synthesis), Fluorenes (chemical synthesis), Gadolinium (chemistry), Heterocyclic Compounds, 1-Ring (chemistry), Ligands, Macromolecular Substances, Molecular Structure, Peptides (chemical synthesis).
MESH :
- chemical , chemical synthesis : Amino Acids, Fluorenes, Peptides.
- chemical , chemistry : Gadolinium, Heterocyclic Compounds, 1-Ring.
- chemical : Ligands, Macromolecular Substances.
- Molecular Structure.

Abstract

A general synthetic route to two DOTA-linked N-Fmoc amino acids (DOTA-F and DOTA-K) is described that allows insertion of DOTA at any endo-position within a peptide sequence. Three model pentapeptides were prepared to test the general utility of these derivatives in solid-phase peptide synthesis. Both DOTA derivatives reacted smoothly by means of standard HBTU activation chemistry to the point of insertion of the DOTA amino acid, but extension of the peptide chain beyond the DOTA-amino acid insertion required the use of pre-activated C-pentafluorophenyl ester N-alpha-Fmoc amino acids. Three Gal-80 binding peptides (12-mers) were then prepared by using this methodology with DOTA positioned either at the N terminus or at one of two different internal positions;the binding of the resulting GdDOTA-12-mers to Gal-80 were compared. The methodology described here allows versatile, controlled introduction of DOTA into any location within a peptide sequence. This provides a potential method for the screening of libraries of DOTA-linked peptides for optimal targeting properties.

DOI: 10.1002/chem.200305389
PubMed: 15007806

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Le document en format XML

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<author><name sortKey="De Le N Rodriguez, Luis M" sort="De Le N Rodriguez, Luis M" uniqKey="De Le N Rodriguez L" first="Luis M" last="De Le N-Rodriguez">Luis M. De Le N-Rodriguez</name>
<affiliation wicri:level="1"><nlm:affiliation>Department of Chemistry, University of Texas at Dallas, P.O. Box 830688, Richardson, TX 75083, USA.</nlm:affiliation>
<country xml:lang="fr">États-Unis</country>
<wicri:regionArea>Department of Chemistry, University of Texas at Dallas, P.O. Box 830688, Richardson, TX 75083</wicri:regionArea>
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<author><name sortKey="Kovacs, Zoltan" sort="Kovacs, Zoltan" uniqKey="Kovacs Z" first="Zoltan" last="Kovacs">Zoltan Kovacs</name>
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<author><name sortKey="Dieckmann, Gregg R" sort="Dieckmann, Gregg R" uniqKey="Dieckmann G" first="Gregg R" last="Dieckmann">Gregg R. Dieckmann</name>
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<author><name sortKey="Sherry, A Dean" sort="Sherry, A Dean" uniqKey="Sherry A" first="A Dean" last="Sherry">A Dean Sherry</name>
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<term>Gadolinium ()</term>
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<term>Structures macromoléculaires</term>
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</keywords>
<keywords scheme="MESH" xml:lang="fr"><term>Composés hétéromonocycliques</term>
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<front><div type="abstract" xml:lang="en">A general synthetic route to two DOTA-linked N-Fmoc amino acids (DOTA-F and DOTA-K) is described that allows insertion of DOTA at any endo-position within a peptide sequence. Three model pentapeptides were prepared to test the general utility of these derivatives in solid-phase peptide synthesis. Both DOTA derivatives reacted smoothly by means of standard HBTU activation chemistry to the point of insertion of the DOTA amino acid, but extension of the peptide chain beyond the DOTA-amino acid insertion required the use of pre-activated C-pentafluorophenyl ester N-alpha-Fmoc amino acids. Three Gal-80 binding peptides (12-mers) were then prepared by using this methodology with DOTA positioned either at the N terminus or at one of two different internal positions;the binding of the resulting GdDOTA-12-mers to Gal-80 were compared. The methodology described here allows versatile, controlled introduction of DOTA into any location within a peptide sequence. This provides a potential method for the screening of libraries of DOTA-linked peptides for optimal targeting properties.</div>
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<Abstract><AbstractText>A general synthetic route to two DOTA-linked N-Fmoc amino acids (DOTA-F and DOTA-K) is described that allows insertion of DOTA at any endo-position within a peptide sequence. Three model pentapeptides were prepared to test the general utility of these derivatives in solid-phase peptide synthesis. Both DOTA derivatives reacted smoothly by means of standard HBTU activation chemistry to the point of insertion of the DOTA amino acid, but extension of the peptide chain beyond the DOTA-amino acid insertion required the use of pre-activated C-pentafluorophenyl ester N-alpha-Fmoc amino acids. Three Gal-80 binding peptides (12-mers) were then prepared by using this methodology with DOTA positioned either at the N terminus or at one of two different internal positions;the binding of the resulting GdDOTA-12-mers to Gal-80 were compared. The methodology described here allows versatile, controlled introduction of DOTA into any location within a peptide sequence. This provides a potential method for the screening of libraries of DOTA-linked peptides for optimal targeting properties.</AbstractText>
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Solid-phase synthesis of DOTA-peptides.

Solid-phase synthesis of DOTA-peptides.

Source :

Descripteurs français

English descriptors

Abstract

Links toward previous steps (curation, corpus...)

Links to Exploration step

Le document en format XML

Pour manipuler ce document sous Unix (Dilib)

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Pour générer des pages wiki