C-Linked Glycomimetic Libraries Accessed by the Passerini Reaction

Vlahoviček-Kahlina, Kristina; Suć Sajko, Josipa; Jerić, Ivanka

doi:10.3390/ijms20246236

Open AccessArticle

C-Linked Glycomimetic Libraries Accessed by the Passerini Reaction

by

Kristina Vlahoviček-Kahlina

,

Josipa Suć Sajko

and

Ivanka Jerić

^*

Division of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, Bijenička cesta 54, 10000 Zagreb, Croatia

^*

Author to whom correspondence should be addressed.

Int. J. Mol. Sci. 2019, 20(24), 6236; https://doi.org/10.3390/ijms20246236

Submission received: 25 November 2019 / Revised: 6 December 2019 / Accepted: 9 December 2019 / Published: 10 December 2019

(This article belongs to the Section Physical Chemistry and Chemical Physics)

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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 α-hydroxy C-glycosyl acids or more complex systems was elaborated by simple post-condensation methodologies.

Keywords: multicomponent reactions; carbohydrates; diastereoselective synthesis; glycosylation; C-glycosides

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MDPI and ACS Style

Vlahoviček-Kahlina, K.; Suć Sajko, J.; Jerić, I. C-Linked Glycomimetic Libraries Accessed by the Passerini Reaction. Int. J. Mol. Sci. 2019, 20, 6236. https://doi.org/10.3390/ijms20246236

AMA Style

Vlahoviček-Kahlina K, Suć Sajko J, Jerić I. C-Linked Glycomimetic Libraries Accessed by the Passerini Reaction. International Journal of Molecular Sciences. 2019; 20(24):6236. https://doi.org/10.3390/ijms20246236

Chicago/Turabian Style

Vlahoviček-Kahlina, Kristina, Josipa Suć Sajko, and Ivanka Jerić. 2019. "C-Linked Glycomimetic Libraries Accessed by the Passerini Reaction" International Journal of Molecular Sciences 20, no. 24: 6236. https://doi.org/10.3390/ijms20246236

APA Style

Vlahoviček-Kahlina, K., Suć Sajko, J., & Jerić, I. (2019). C-Linked Glycomimetic Libraries Accessed by the Passerini Reaction. International Journal of Molecular Sciences, 20(24), 6236. https://doi.org/10.3390/ijms20246236

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C-Linked Glycomimetic Libraries Accessed by the Passerini Reaction

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