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Modern Trends in Glycochemistry
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Modern Trends in Glycochemistry

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

Deadline for manuscript submissions: closed (30 April 2023) | Viewed by 6901

Special Issue Editor

Prof. Dr. Vinod Kumar Tiwari

E-Mail Website
Guest Editor
Department of Chemistry, Institute of Science, Banaras Hindu University, Varanasi 221005, India
Interests: synthetic carbohydrate chemistry; organic synthesis; carbohydrates in drug development

Special Issue Information

Dear Colleagues,

The major objective of this thematic issue of Molecules on the topic ‘Modern Trends in Glycochemistry’ is to present an extensive information about the growing importance of carbohydrates in medicinal chemistry. Carbohydrate is one of the most abundant natural products and is considered to be an extremely valuable scaffold explored in chemistry, biology, and medicines for various purposes. Its pivotal role in a number of important biological events, such as energy storage, transport, intercellular adhesion, malignant transformation, signal transduction, modulation of protein function, viral and bacterial cell surface recognition, etc., may be of considerable pharmacological importance. Further, its notable characteristics, such as its wide availability, structural diversity, and functionality rich with chirality, are some more additional fascinating features that could again enhance its widespread applications in various emerging fields. This chemical and biological significance of carbohydrates is thus attracting chemists, biochemists, and medicinal chemists toward considering this biomolecule in basic and advanced research.

This Special Issue of Molecules examines the notable developments in the fields, including the synthesis, biology, and therapeutic applications of carbohydrates. Therefore, we are pleased to welcome contributions from experts actively engaged in various emerging aspects of carbohydrates, including their synthesis, modification, characterization, and application in chemistry and medicines. The topics to be covered in this Special Issue are broad, and the aim is to present an advanced aspect of carbohydrate-based molecular scaffolding followed by detailed information about the importance of carbohydrates, ranging from chemical biology to catalysis and from material science to medicinal chemistry.

Prof. Dr. Vinod Kumar Tiwari
Guest Editor

Manuscript Submission Information

Manuscripts should be submitted online at www.mdpi.com by registering and logging in to this website. Once you are registered, click here to go to the submission form. Manuscripts can be submitted until the deadline. All submissions that pass pre-check are peer-reviewed. Accepted papers will be published continuously in the journal (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as short communications are invited. For planned papers, a title and short abstract (about 100 words) can be sent to the Editorial Office for announcement on this website.

Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Molecules is an international peer-reviewed open access semimonthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 2700 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

  • carbohydrates
  • glycoconjugates
  • glycosylation methodology
  • protection/deprotection strategies in carbohydrates
  • enzymatic synthesis of carbohydrates
  • chemistry and biology of sialic acids
  • chemistry and biology of iminosugars
  • neoglycoconjugates and glycocodendrimers
  • glycan microarrays

Published Papers (3 papers)

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Research

14 pages, 2774 KiB  
Article
Investigation of the Protective Effect for GcMAF by a Glycosidase Inhibitor and the Glycan Structure of Gc Protein
by Yoshimi Kanie, Yuya Maegawa, Yi Wei and Osamu Kanie
Molecules 2023, 28(4), 1570; https://doi.org/10.3390/molecules28041570 - 6 Feb 2023
Cited by 2 | Viewed by 2808
Abstract
O-linked α-N-acetylgalactosamine (α-GalNAc) in the Gc protein is essential for macrophage activation; thus, the GalNAc-attached form of Gc protein is called Gc macrophage activating factor (GcMAF). O-linked glycans in Gc proteins from human plasma mainly consist of trisaccharides. GcMAF [...] Read more.
O-linked α-N-acetylgalactosamine (α-GalNAc) in the Gc protein is essential for macrophage activation; thus, the GalNAc-attached form of Gc protein is called Gc macrophage activating factor (GcMAF). O-linked glycans in Gc proteins from human plasma mainly consist of trisaccharides. GcMAF is produced when glycans on the Gc protein are hydrolyzed by α-Sia-ase and β-Gal-ase, leaving an α-GalNAc. Upon hydrolysis of α-GalNAc present on GcMAF, the protein loses the macrophage-activating effect. In contrast, our synthesized pyrrolidine-type iminocyclitol possessed strong in vitro α-GalNAc-ase inhibitory activity. In this study, we examined the protective effects of iminocyclitol against GcMAF via inhibition of α-GalNAc-ase activity. Detailed mass spectrometric analyses revealed the protective effect of the inhibitor on GcMAF. Furthermore, structural information regarding the glycosylation site and glycan structure was obtained using tandem mass spectrometric (MS/MS) analysis of the glycosylated peptides after tryptic digestion. Full article
(This article belongs to the Special Issue Modern Trends in Glycochemistry)
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13 pages, 10536 KiB  
Article
SnCl4 Promoted Efficient Cleavage of Acetal/Ketal Groups with the Assistance of Water in CH2Cl2
by Tao Luo, Tian-Tian Xu, Yang-Fan Guo and Hai Dong
Molecules 2022, 27(23), 8258; https://doi.org/10.3390/molecules27238258 - 26 Nov 2022
Cited by 2 | Viewed by 1756
Abstract
Acetalization and deacetalation are a pair of routine manipulations to protect and deprotect the 4- and 6-hydroxyl groups of glycosides in the synthesis of glycosyl building blocks. In this study, we found that treatment of SnCl4 with various carbohydrates containing acetal/ketal groups [...] Read more.
Acetalization and deacetalation are a pair of routine manipulations to protect and deprotect the 4- and 6-hydroxyl groups of glycosides in the synthesis of glycosyl building blocks. In this study, we found that treatment of SnCl4 with various carbohydrates containing acetal/ketal groups with the assistance of water in CH2Cl2 led to deacetalization/deketalization products in almost quantitative yields. In addition, for substrates containing both acetal/ketal and p-methoxylbenzyl groups, we also found that the p-methoxylbenzyl group was selectively cleaved by the use of a catalytic amount of SnCl4, while the acetal/ketal groups remained. Furthermore, based on this, 4,6-benzylidene glycosides can be conveniently converted to 4,6-OAc or 4-OH, 6-OAc glycosides. Full article
(This article belongs to the Special Issue Modern Trends in Glycochemistry)
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7 pages, 996 KiB  
Article
Glycosyl Formates: Glycosylations with Neighboring-Group Participation
by Liang Yang and Christian Marcus Pedersen
Molecules 2022, 27(19), 6244; https://doi.org/10.3390/molecules27196244 - 22 Sep 2022
Cited by 1 | Viewed by 1868
Abstract
Protected 2-O-benzyolated glycosyl formates were synthesized in one-step from the corresponding orthoester using formic acid as the sole reagent. Glucopyranosyl, mannopyranosyl and galactopyranosyl donors were synthesized and their glycosylation properties studied using model glycosyl acceptors of varied steric bulk and reactivity. Bismuth triflate [...] Read more.
Protected 2-O-benzyolated glycosyl formates were synthesized in one-step from the corresponding orthoester using formic acid as the sole reagent. Glucopyranosyl, mannopyranosyl and galactopyranosyl donors were synthesized and their glycosylation properties studied using model glycosyl acceptors of varied steric bulk and reactivity. Bismuth triflate was the preferred catalyst and KPF6 was used as an additive. The 1,2-trans-selectivities resulting from neighboring-group participation were excellent and the glycosylations were generally high-yielding. Full article
(This article belongs to the Special Issue Modern Trends in Glycochemistry)
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