C-Linked Glycomimetic Libraries Accessed by the Passerini Reaction

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 compris...

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Bibliographic Details
Published in:International journal of molecular sciences 2019-12, Vol.20 (24), p.6236
Main Authors: Vlahoviček-Kahlina, Kristina, Suć Sajko, Josipa, Jerić, Ivanka
Format: Article
Language:English
Subjects:
Aldehydes
Aldehydes - chemical synthesis
Aldehydes - chemistry
Alkenes - chemistry
Amino acids
Binding sites
Biological Mimicry
Carbohydrates
Carbon
Complex systems
Condensates
Glycoconjugates
Glycoconjugates - chemistry
Glycosylation
Ketones
Ketones - chemical synthesis
Ketones - chemistry
Molecular Structure
Natural products
Small Molecule Libraries - chemical synthesis
Small Molecule Libraries - chemistry
Stereoisomerism
Stereoselectivity
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Summary: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 α-hydroxy C-glycosyl acids or more complex systems was elaborated by simple post-condensation methodologies.
ISSN:1422-0067
1661-6596
1422-0067
DOI:10.3390/ijms20246236