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C-Linked Glycomimetic Libraries Accessed by the Passerini Reaction.

ABSTRACT: Carbohydrates and their conjugates are the most abundant natural products, with diverse and highly important biological roles. Synthetic glycoconjugates are versatile tools used to probe biological systems and interfere with them. In an endeavor to provide an efficient route to glycomimetics comprising structurally diverse carbohydrate units, we describe herein a robust, stereoselective, multicomponent approach. Isopropylidene-protected carbohydrate-derived aldehydes and ketones were utilized in the Passerini reaction, giving different glycosylated structures in high yields and diastereoselectivities up to 90:10 diastereomeric ratio (d.r). Access to highly valuable building blocks based on ?-hydroxy C-glycosyl acids or more complex systems was elaborated by simple post-condensation methodologies.

SUBMITTER: Vlahovicek-Kahlina K

PROVIDER: S-EPMC6940731 | biostudies-literature | 2019 Dec

REPOSITORIES: biostudies-literature

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C-Linked Glycomimetic Libraries Accessed by the Passerini Reaction.

Vlahoviček-Kahlina Kristina K Suć Sajko Josipa J Jerić Ivanka I

International journal of molecular sciences 20191210 24

Carbohydrates and their conjugates are the most abundant natural products, with diverse and highly important biological roles. Synthetic glycoconjugates are versatile tools used to probe biological systems and interfere with them. In an endeavor to provide an efficient route to glycomimetics comprising structurally diverse carbohydrate units, we describe herein a robust, stereoselective, multicomponent approach. Isopropylidene-protected carbohydrate-derived aldehydes and ketones were utilized in ...[more]

PMID: 31835639

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