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Recent Advances in Glycochemistry

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Chemical Biology".

Deadline for manuscript submissions: closed (28 February 2023) | Viewed by 6548

Special Issue Editor


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Special Issue Information

Dear Colleagues,

Carbohydrates are, indeed, the most abundant class of natural products. Multifunctional and stereochemically rich molecules, they act as unique scaffolds for the preparation of a diversity of compounds with industrial applications as pharmaceuticals, in cosmetics, and in food, among others. In addition, these molecules are important in cell adhesion, host–pathogen interaction, and many relevant biological processes, encouraging chemists to find the key carbohydrate structures to uncover the secrets of nature in human health and disease.

Organic chemistry starting from carbohydrates, either unprotected or functionalized, is indeed challenging. These abundant, renewable and low-cost materials also provide a structural diversity prompt for innovation and a more sustainable future.

This Special Issue covers the latest findings on the chemistry of carbohydrates, including methodologies for the generation of carbohydrates and carbohydrate mimetics. Glycoconjugation chemistry is an important tool for the production of biological molecules, and advances in this topic are welcome, as well as catalysis in carbohydrate chemistry, carbohydrate green chemistry,  and the usefulness of carbohydrates in ionic liquid preparation and applications.


Prof. Dr. Amélia Pilar Rauter
Guest Editor

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Keywords

  • Carbohydrates
  • Synthesis
  • Glycoconjugation
  • Carbohydrate mimetics
  • Catalysis
  • Ionic liquids
  • Green chemistry

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Published Papers (2 papers)

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Research

10 pages, 4839 KiB  
Article
The Synthesis of Blood Group Antigenic A Trisaccharide and Its Biotinylated Derivative
by Ekaterina D. Kazakova, Dmitry V. Yashunsky and Nikolay E. Nifantiev
Molecules 2021, 26(19), 5887; https://doi.org/10.3390/molecules26195887 - 28 Sep 2021
Cited by 3 | Viewed by 2179
Abstract
Blood group antigenic A trisaccharide represents the terminal residue of all A blood group antigens and plays a key role in blood cell recognition and blood group compatibility. Herein, we describe the synthesis of the spacered A trisaccharide by means of an assembly [...] Read more.
Blood group antigenic A trisaccharide represents the terminal residue of all A blood group antigens and plays a key role in blood cell recognition and blood group compatibility. Herein, we describe the synthesis of the spacered A trisaccharide by means of an assembly scheme that employs in its most complex step the recently proposed glycosyl donor of the 2-azido-2-deoxy-selenogalactoside type, bearing stereocontrolling 3-O-benzoyl and 4,6-O-(di-tert-butylsilylene)-protecting groups. Its application provided efficient and stereoselective formation of the required α-glycosylation product, which was then deprotected and subjected to spacer biotinylation to give both target products, which are in demand for biochemical studies. Full article
(This article belongs to the Special Issue Recent Advances in Glycochemistry)
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20 pages, 2825 KiB  
Article
Facile Synthesis of Saikosaponins
by Ziqiang Wang, Bingcheng Wei, Tong Mu, Peng Xu and Biao Yu
Molecules 2021, 26(7), 1941; https://doi.org/10.3390/molecules26071941 - 30 Mar 2021
Cited by 4 | Viewed by 3310
Abstract
Saikosaponin A (SSa) and D (SSd) are typical oleanane-type saponins featuring a unique 13,28-epoxy-ether moiety at D ring of the aglycones, which exhibit a wide range of biological and pharmacological activities. Herein, we report the first synthesis of saikosaponin A/D (1 [...] Read more.
Saikosaponin A (SSa) and D (SSd) are typical oleanane-type saponins featuring a unique 13,28-epoxy-ether moiety at D ring of the aglycones, which exhibit a wide range of biological and pharmacological activities. Herein, we report the first synthesis of saikosaponin A/D (12) and their natural congeners, including prosaikosaponin F (3), G (4), saikosaponin Y (5), prosaikogenin (6), and clinoposaponin I (7). The present synthesis features ready preparation of the aglycones of high oxidation state from oleanolic acid, regioselective glycosylation to construct the β-(1→3)-linked disaccharide fragment, and efficient gold(I)-catalyzed glycosylation to install the glycans on to the aglycones. Full article
(This article belongs to the Special Issue Recent Advances in Glycochemistry)
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