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

ABSTRACT: 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.

SUBMITTER: Abdildinova A

PROVIDER: S-EPMC8693395 | biostudies-literature | 2020 Dec

REPOSITORIES: biostudies-literature

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

Abdildinova Aizhan A Gong Young-Dae YD

RSC advances 20201201 2

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 <i>via</i> an Fmoc solid-phase p ...[more]

PMID: 35423674

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