Document Type

Article

Publication Date

2021

DOI

10.3390/molecules26113394

Publication Title

Molecules

Volume

26

Issue

11

Pages

1-26

Abstract

Glycomacrolactones exhibit many interesting biological properties, and they are also important in molecular recognitions and for supramolecular chemistry. Therefore, it is important to be able to access glycomacrocycles with different sizes and functionality. A new series of carbohydrate-based macrocycles containing triazole and lactone moieties have been designed and synthesized. The synthesis features an intramolecular nucleophilic substitution reaction for the macrocyclization step. In this article, the effect of some common sulfonate leaving groups is evaluated for macrolactonization. Using tosylate gave good selectivity for monolactonization products with good yields. Fourteen different macrocycles have been synthesized and characterized, of which eleven macrocycles are from cyclization of the C1 to C6 positions of N-acetyl D-glucosamine derivatives and three others from C2 to C6 cyclization of functionalized D-glucosamine derivatives. These novel macrolactones have unique structures and demonstrate interesting anion binding properties, especially for chloride. The macrocycles containing two triazoles form complexes with copper sulfate, and they are effective ligands for copper sulfate mediated azide-alkyne cycloaddition reactions (CuAAC). In addition, several macrocycles show some selectivity for different alkynes.

Comments

© 2021 by the authors.

This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Publisher's version available at: https://doi.org/10.3390/molecules26113394

Original Publication Citation

Adhikari, S. B., Chen, A., & Wang, G. (2021). Synthesis of carbohydrate based macrolactones and their applications as receptors for ion recognition and catalysis. Molecules, 26(11), Article 3394, 1-26. https://doi.org/10.3390/molecules26113394

ORCID

0000-0002-8943-9663 (Chen)

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