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Protein-Carbohydrate Conjugates: Synthesis and Application

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

Deadline for manuscript submissions: closed (31 March 2023) | Viewed by 8075

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Special Issue Editors

Prof. Dr. Katherine A. Wall

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Guest Editor

Department of Medicinal and Biological Chemistry, The University of Toledo Health Science Campus, Toledo, OH 43614, USA
Interests: glycopeptides; anti-cancer vaccines; T cells; rhamnose; MUC1; NAADP; autoimmune disease
Special Issues, Collections and Topics in MDPI journals

Prof. Dr. Steven J. Sucheck

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Guest Editor

Department of Chemistry and Biochemistry, The University of Toledo, Toledo, OH 43606, USA
Interests: organic chemistry, medicinal chemistry, carbohydrates, infectious disease; vaccines

Special Issue Information

Dear Colleagues,

Production of recombinant proteins has allowed tremendous progress in basic studies of protein structure and function as well as in their application as vaccines or biologic drugs. The production of protein-carbohydrate conjugates will similarly allow progress in the study and use of carbohydrates in combination with proteins as biomolecules. This issue focuses on new approaches to synthesis and application of protein-carbohydrate conjugates in basic science, vaccines, and other biopharmaceutical areas.

Prof. Dr. Katherine Wall
Prof. Dr. Steven J. Sucheck
Guest Editors

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Keywords

Protein-carbohydrate conjugation
Carbohydrate synthesis
Vaccines
Carbohydrates in immune responses
Biopharmaceuticals

Published Papers (3 papers)

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Research

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16 pages, 1951 KiB

Open AccessArticle

Specific Recognition of β-Galactofuranose-Containing Glycans of Synthetic Neoglycoproteins by Sera of Chronic Chagas Disease Patients

by Alba L. Montoya, Eileni R. Gil, Emily L. Heydemann, Igor L. Estevao, Bianca E. Luna, Cameron C. Ellis, Sohan R. Jankuru, Belkisyolé Alarcón de Noya, Oscar Noya, Maria Paola Zago, Igor C. Almeida and Katja Michael

Molecules 2022, 27(2), 411; https://doi.org/10.3390/molecules27020411 - 09 Jan 2022

Cited by 5 | Viewed by 2124

Abstract

Chagas disease (CD) can be accurately diagnosed by detecting Trypanosoma cruzi in patients’ blood using polymerase chain reaction (PCR). However, parasite-derived biomarkers are of great interest for the serological diagnosis and early evaluation of chemotherapeutic efficacy when PCR may fail, owing to a blood parasite load below the method’s limit of detection. Previously, we focused on the detection of specific anti-α-galactopyranosyl (α-Gal) antibodies in chronic CD (CCD) patients elicited by α-Gal glycotopes copiously expressed on insect-derived and mammal-dwelling infective parasite stages. Nevertheless, these stages also abundantly express cell surface glycosylphosphatidylinositol (GPI)-anchored glycoproteins and glycoinositolphospholipids (GIPLs) bearing nonreducing terminal β-galactofuranosyl (β-Galf) residues, which are equally foreign to humans and, therefore, highly immunogenic. Here we report that CCD patients’ sera react specifically with synthetic β-Galf-containing glycans. We took a reversed immunoglycomics approach that entailed: (a) Synthesis of T. cruzi GIPL-derived Galfβ1,3Manpα-(CH₂)₃SH (glycan G29_SH) and Galfβ1,3Manpα1,2-[Galfβ1,3]Manpα-(CH₂)₃SH (glycan G32_SH); and (b) preparation of neoglycoproteins NGP29b and NGP32b, and their evaluation in a chemiluminescent immunoassay. Receiver-operating characteristic analysis revealed that NGP32b can distinguish CCD sera from sera of healthy individuals with 85.3% sensitivity and 100% specificity. This suggests that Galfβ1,3Manpα1,2-[Galfβ1,3]Manpα is an immunodominant glycotope and that NGP32b could potentially be used as a novel CCD biomarker. Full article

(This article belongs to the Special Issue Protein-Carbohydrate Conjugates: Synthesis and Application)

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20 pages, 1361 KiB

Open AccessArticle

A Neoglycoprotein-Immobilized Fluorescent Magnetic Bead Suspension Multiplex Array for Galectin-Binding Studies

by Libo Zhang, Hai Yu, Yuanyuan Bai, Bijoyananda Mishra, Xiaoxiao Yang, Jing Wang, Evan B. Yu, Riyao Li and Xi Chen

Molecules 2021, 26(20), 6194; https://doi.org/10.3390/molecules26206194 - 14 Oct 2021

Cited by 1 | Viewed by 2950

Abstract

Carbohydrate-protein conjugates have diverse applications. They have been used clinically as vaccines against bacterial infection and have been developed for high-throughput assays to elucidate the ligand specificities of glycan-binding proteins (GBPs) and antibodies. Here, we report an effective process that combines highly efficient chemoenzymatic synthesis of carbohydrates, production of carbohydrate-bovine serum albumin (glycan-BSA) conjugates using a squarate linker, and convenient immobilization of the resulting neoglycoproteins on carboxylate-coated fluorescent magnetic beads for the development of a suspension multiplex array platform. A glycan-BSA-bead array containing BSA and 50 glycan-BSA conjugates with tuned glycan valency was generated. The binding profiles of six plant lectins with binding preference towards Gal and/or GalNAc, as well as human galectin-3 and galectin-8, were readily obtained. Our results provide useful information to understand the multivalent glycan-binding properties of human galectins. The neoglycoprotein-immobilized fluorescent magnetic bead suspension multiplex array is a robust and flexible platform for rapid analysis of glycan and GBP interactions and will find broad applications. Full article

(This article belongs to the Special Issue Protein-Carbohydrate Conjugates: Synthesis and Application)

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Review

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19 pages, 9471 KiB

Open AccessReview

Homo- and Heterogeneous Glycoconjugates on the Basis of N-Glycans and Human Serum Albumin: Synthesis and Biological Evaluation

by Almira Kurbangalieva, Regina Zamalieva, Igor Nasibullin, Kenshiro Yamada and Katsunori Tanaka

Molecules 2022, 27(4), 1285; https://doi.org/10.3390/molecules27041285 - 14 Feb 2022

Cited by 2 | Viewed by 1986

Abstract

Neoglycoconjugates mimicking natural compounds and possessing a variety of biological functions are very successful tools for researchers to understand the general mechanisms of many biological processes in living organisms. These substances are characterized by high biotolerance and specificity, with low toxicity. Due to the difficult isolation of individual glycoclusters from biological objects, special interest has been directed toward synthetic analogs. This review is mainly focused on the one-pot, double-click methodology (containing alkyne–azide click cycloaddition with the following 6π-azaelectrocyclization reactions) used in the synthesis of N-glycoconjugates. Homogeneous (including one type of biantennary N-glycan fragments) and heterogeneous (containing two to four types of biantennary N-glycan fragments) glycoclusters on albumin were synthesized via this strategy. A series of cell-, tissue- and animal-based experiments proved glycoclusters to be a very promising class of targeted delivery systems. Depending on the oligosaccharide units combined in the cluster, their amount, and arrangement relative to one another, conjugates can recognize various cells, including cancer cells, with high selectivity. These results open new perspectives for affected tissue visualization and treatment. Full article

(This article belongs to the Special Issue Protein-Carbohydrate Conjugates: Synthesis and Application)

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