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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....
Autores principales: | , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
The Royal Society of Chemistry
2021
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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. |
format | Online Article Text |
id | pubmed-8693395 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2021 |
publisher | The Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
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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