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Traceless solid-phase synthesis and β-turn propensity of 1,3-thiazole-based peptidomimetics

The design and solid-phase synthesis of 1,3-thiazole-based peptidomimetic molecules is described. The solid-phase synthesis was based on the utilization of a traceless linker strategy. The synthesis starts from the conversion of chloromethyl polystyrene resin to the resin with a sulfur linker unit....

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Autores principales: Abdildinova, Aizhan, Gong, Young-Dae
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2021
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8693395/
https://www.ncbi.nlm.nih.gov/pubmed/35423674
http://dx.doi.org/10.1039/d0ra10127c
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author Abdildinova, Aizhan
Gong, Young-Dae
author_facet Abdildinova, Aizhan
Gong, Young-Dae
author_sort Abdildinova, Aizhan
collection PubMed
description The design and solid-phase synthesis of 1,3-thiazole-based peptidomimetic molecules is described. The solid-phase synthesis was based on the utilization of a traceless linker strategy. The synthesis starts from the conversion of chloromethyl polystyrene resin to the resin with a sulfur linker unit. The key intermediate 4-amino-thiazole-5-carboxylic acid resin is prepared in three steps from Merrifield resin. The amide coupling proceeded at the C4 and C5 positions via an Fmoc solid-phase peptide synthesis strategy. After cleavage, the final compounds were obtained in moderate yields (average 9%, 11-step overall yields) with high purities (≥87%). Geometric measurements of Cα distances and dihedral angles along with an rmsd of 0.5434 for attachment with Cα of the β-turn template suggest type IV β-turn structural motifs. Additionally, the physicochemical properties of the molecules have been evaluated.
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spelling pubmed-86933952022-04-13 Traceless solid-phase synthesis and β-turn propensity of 1,3-thiazole-based peptidomimetics Abdildinova, Aizhan Gong, Young-Dae RSC Adv Chemistry The design and solid-phase synthesis of 1,3-thiazole-based peptidomimetic molecules is described. The solid-phase synthesis was based on the utilization of a traceless linker strategy. The synthesis starts from the conversion of chloromethyl polystyrene resin to the resin with a sulfur linker unit. The key intermediate 4-amino-thiazole-5-carboxylic acid resin is prepared in three steps from Merrifield resin. The amide coupling proceeded at the C4 and C5 positions via an Fmoc solid-phase peptide synthesis strategy. After cleavage, the final compounds were obtained in moderate yields (average 9%, 11-step overall yields) with high purities (≥87%). Geometric measurements of Cα distances and dihedral angles along with an rmsd of 0.5434 for attachment with Cα of the β-turn template suggest type IV β-turn structural motifs. Additionally, the physicochemical properties of the molecules have been evaluated. The Royal Society of Chemistry 2021-01-04 /pmc/articles/PMC8693395/ /pubmed/35423674 http://dx.doi.org/10.1039/d0ra10127c Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Abdildinova, Aizhan
Gong, Young-Dae
Traceless solid-phase synthesis and β-turn propensity of 1,3-thiazole-based peptidomimetics
title Traceless solid-phase synthesis and β-turn propensity of 1,3-thiazole-based peptidomimetics
title_full Traceless solid-phase synthesis and β-turn propensity of 1,3-thiazole-based peptidomimetics
title_fullStr Traceless solid-phase synthesis and β-turn propensity of 1,3-thiazole-based peptidomimetics
title_full_unstemmed Traceless solid-phase synthesis and β-turn propensity of 1,3-thiazole-based peptidomimetics
title_short Traceless solid-phase synthesis and β-turn propensity of 1,3-thiazole-based peptidomimetics
title_sort traceless solid-phase synthesis and β-turn propensity of 1,3-thiazole-based peptidomimetics
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8693395/
https://www.ncbi.nlm.nih.gov/pubmed/35423674
http://dx.doi.org/10.1039/d0ra10127c
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