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Solid-Phase Synthesis of Tetrahydropyridazinedione-Constrained Peptides

[Image: see text] The design and solid-phase synthesis of tetrahydropyridazine-3,6-dione (Tpd) peptidomimetics derived from backbone-aminated peptides is reported. The described protocol features the synthesis of chiral α-hydrazino acids suitable for chemoselective incorporation into growing peptide...

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Autores principales: Kang, Chang Won, Ranatunga, Sujeewa, Sarnowski, Matthew P., Del Valle, Juan R.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2014
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4201324/
https://www.ncbi.nlm.nih.gov/pubmed/25295511
http://dx.doi.org/10.1021/ol5026684
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author Kang, Chang Won
Ranatunga, Sujeewa
Sarnowski, Matthew P.
Del Valle, Juan R.
author_facet Kang, Chang Won
Ranatunga, Sujeewa
Sarnowski, Matthew P.
Del Valle, Juan R.
author_sort Kang, Chang Won
collection PubMed
description [Image: see text] The design and solid-phase synthesis of tetrahydropyridazine-3,6-dione (Tpd) peptidomimetics derived from backbone-aminated peptides is reported. The described protocol features the synthesis of chiral α-hydrazino acids suitable for chemoselective incorporation into growing peptide chains. Acid-catalyzed cyclization to form the Tpd ring during cleavage affords the target peptidomimetics in good yield and purity. The scope of Tpd incorporation is demonstrated through the synthesis of constrained peptides featuring nucleophilic/electrophilic side chains and sterically encumbered α-substituted hydrazino acid residues.
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spelling pubmed-42013242015-10-08 Solid-Phase Synthesis of Tetrahydropyridazinedione-Constrained Peptides Kang, Chang Won Ranatunga, Sujeewa Sarnowski, Matthew P. Del Valle, Juan R. Org Lett [Image: see text] The design and solid-phase synthesis of tetrahydropyridazine-3,6-dione (Tpd) peptidomimetics derived from backbone-aminated peptides is reported. The described protocol features the synthesis of chiral α-hydrazino acids suitable for chemoselective incorporation into growing peptide chains. Acid-catalyzed cyclization to form the Tpd ring during cleavage affords the target peptidomimetics in good yield and purity. The scope of Tpd incorporation is demonstrated through the synthesis of constrained peptides featuring nucleophilic/electrophilic side chains and sterically encumbered α-substituted hydrazino acid residues. American Chemical Society 2014-10-08 2014-10-17 /pmc/articles/PMC4201324/ /pubmed/25295511 http://dx.doi.org/10.1021/ol5026684 Text en Copyright © 2014 American Chemical Society Terms of Use (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html)
spellingShingle Kang, Chang Won
Ranatunga, Sujeewa
Sarnowski, Matthew P.
Del Valle, Juan R.
Solid-Phase Synthesis of Tetrahydropyridazinedione-Constrained Peptides
title Solid-Phase Synthesis of Tetrahydropyridazinedione-Constrained Peptides
title_full Solid-Phase Synthesis of Tetrahydropyridazinedione-Constrained Peptides
title_fullStr Solid-Phase Synthesis of Tetrahydropyridazinedione-Constrained Peptides
title_full_unstemmed Solid-Phase Synthesis of Tetrahydropyridazinedione-Constrained Peptides
title_short Solid-Phase Synthesis of Tetrahydropyridazinedione-Constrained Peptides
title_sort solid-phase synthesis of tetrahydropyridazinedione-constrained peptides
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4201324/
https://www.ncbi.nlm.nih.gov/pubmed/25295511
http://dx.doi.org/10.1021/ol5026684
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