Sucrose-Based Macrocycles: An Update

Sucrose is by far the most abundant disaccharide found in nature, consisting of two simple hexose units: <span style="font-variant: small-caps;">d</span>-glucose and <span style="font-variant: small-caps;">d</span>-fructose. This exceptionally inexpensive...

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Main Authors: Sławomir Jarosz, Zbigniew Pakulski
Format: Article
Language:English
Published: MDPI AG 2025-06-01
Series:Molecules
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Online Access:https://www.mdpi.com/1420-3049/30/13/2721
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author Sławomir Jarosz
Zbigniew Pakulski
author_facet Sławomir Jarosz
Zbigniew Pakulski
author_sort Sławomir Jarosz
collection DOAJ
description Sucrose is by far the most abundant disaccharide found in nature, consisting of two simple hexose units: <span style="font-variant: small-caps;">d</span>-glucose and <span style="font-variant: small-caps;">d</span>-fructose. This exceptionally inexpensive and widely accessible raw material is produced in virtually limitless quantities. The vast majority is consumed in the food industry either in its native form—as commercial table sugar—or, to a lesser extent, as the basis for artificial sweeteners such as palatinose and sucralose. Beyond its dietary use, sucrose serves as a feedstock for the production of bioethanol, liquid crystals, biodegradable surfactants, and polymers. However, the application of this valuable and extremely cheap raw material (100% optical purity and eight stereogenic centers with precisely defined stereochemistry) in the synthesis of more sophisticated products remains surprisingly limited. In this short review, we focus on the strategic use of the sucrose scaffold in the design and synthesis of fine chemicals. Special attention will be paid to macrocyclic derivatives incorporating the sucrose backbone. These water-soluble structures show promise as molecular receptors within biological environments, offering unique advantages in terms of solubility, biocompatibility, and stereochemical precision.
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spelling doaj-art-161b975febf440918a4e58709e4812512025-08-20T02:36:27ZengMDPI AGMolecules1420-30492025-06-013013272110.3390/molecules30132721Sucrose-Based Macrocycles: An UpdateSławomir Jarosz0Zbigniew Pakulski1Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, PolandInstitute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, PolandSucrose is by far the most abundant disaccharide found in nature, consisting of two simple hexose units: <span style="font-variant: small-caps;">d</span>-glucose and <span style="font-variant: small-caps;">d</span>-fructose. This exceptionally inexpensive and widely accessible raw material is produced in virtually limitless quantities. The vast majority is consumed in the food industry either in its native form—as commercial table sugar—or, to a lesser extent, as the basis for artificial sweeteners such as palatinose and sucralose. Beyond its dietary use, sucrose serves as a feedstock for the production of bioethanol, liquid crystals, biodegradable surfactants, and polymers. However, the application of this valuable and extremely cheap raw material (100% optical purity and eight stereogenic centers with precisely defined stereochemistry) in the synthesis of more sophisticated products remains surprisingly limited. In this short review, we focus on the strategic use of the sucrose scaffold in the design and synthesis of fine chemicals. Special attention will be paid to macrocyclic derivatives incorporating the sucrose backbone. These water-soluble structures show promise as molecular receptors within biological environments, offering unique advantages in terms of solubility, biocompatibility, and stereochemical precision.https://www.mdpi.com/1420-3049/30/13/2721sucrose in fine organic synthesismacrocyclic derivatives with sucrose scaffoldmolecular cages based on sucrose and cycloveratrylenecomplexing properties of macrocycles with sucrose scaffoldsucrose-based molecular switches
spellingShingle Sławomir Jarosz
Zbigniew Pakulski
Sucrose-Based Macrocycles: An Update
Molecules
sucrose in fine organic synthesis
macrocyclic derivatives with sucrose scaffold
molecular cages based on sucrose and cycloveratrylene
complexing properties of macrocycles with sucrose scaffold
sucrose-based molecular switches
title Sucrose-Based Macrocycles: An Update
title_full Sucrose-Based Macrocycles: An Update
title_fullStr Sucrose-Based Macrocycles: An Update
title_full_unstemmed Sucrose-Based Macrocycles: An Update
title_short Sucrose-Based Macrocycles: An Update
title_sort sucrose based macrocycles an update
topic sucrose in fine organic synthesis
macrocyclic derivatives with sucrose scaffold
molecular cages based on sucrose and cycloveratrylene
complexing properties of macrocycles with sucrose scaffold
sucrose-based molecular switches
url https://www.mdpi.com/1420-3049/30/13/2721
work_keys_str_mv AT sławomirjarosz sucrosebasedmacrocyclesanupdate
AT zbigniewpakulski sucrosebasedmacrocyclesanupdate