{"title":"Nitrogen-containing macrocycles having a carbohydrate scaffold.","authors":"Mykhaylo A Potopnyk, Sławomir Jarosz","doi":"10.1016/bs.accb.2024.10.003","DOIUrl":"10.1016/bs.accb.2024.10.003","url":null,"abstract":"<p><p>Nitrogen-containing macrocyclic compounds (amines, amides, and N-heterocyclic derivatives) are important targets in supramolecular chemistry. This article discusses the importance of aza-macrocycles in general and, in particular, those receptors containing sugar unit(s). The combination of a carbohydrate scaffold bearing nitrogen-containing functional groups in macrocyclic molecules opens a convenient route to chiral receptors having potentially useful properties.The carbohydrate-based macrocycles discussed are classified into several general groups: (1) aza-crown ethers containing a carbohydrate sub-unit, (2) cyclic homooligomers from amino sugars, (3) sugar-based cryptands, (4) cyclic peptides containing amino sugar units (including C<sub>2</sub>- and C<sub>3</sub>- symmetrical macrocyclic glycopeptides), (5) nitrogen- containing glycophanes, and (6) 1,2,3-triazoles containing synthetic cyclodextrin analogues. The general strategies employed, as well as specific ones leading to such complex derivatives are surveyed. Applications of such carbohydrate receptors, pointing to their importance as hosts in supramolecular chemistry, are discussed.</p>","PeriodicalId":448936,"journal":{"name":"Advances in carbohydrate chemistry and biochemistry","volume":"86 ","pages":"15-79"},"PeriodicalIF":0.0,"publicationDate":"2024-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142696279","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Alhanouf Z Aljahdali, Pei Shi, Yashan Zhong, George A O'Doherty
{"title":"De novo asymmetric synthesis of the pyranoses: From monosaccharides to oligosaccharides.","authors":"Alhanouf Z Aljahdali, Pei Shi, Yashan Zhong, George A O'Doherty","doi":"10.1016/bs.accb.2024.10.001","DOIUrl":"https://doi.org/10.1016/bs.accb.2024.10.001","url":null,"abstract":"","PeriodicalId":448936,"journal":{"name":"Advances in carbohydrate chemistry and biochemistry","volume":"85 ","pages":"39-107"},"PeriodicalIF":0.0,"publicationDate":"2024-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142690323","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"1-Amino-1-deoxy-d-fructose (\"fructosamine\") and its derivatives.","authors":"Valeri V Mossine, Thomas P Mawhinney","doi":"10.1016/bs.accb.2023.10.002","DOIUrl":"10.1016/bs.accb.2023.10.002","url":null,"abstract":"<p><p>Fructosamine has long been considered as a key intermediate of the Maillard reaction, which to a large extent is responsible for specific aroma, taste, and color formation in thermally processed or dehydrated foods. Since the 1980s, however, as a product of the Amadori rearrangement reaction between glucose and biologically significant amines such as proteins, fructosamine has experienced a boom in biomedical research, mainly due to its relevance to pathologies in diabetes and aging. In this chapter, we assess the scope of the knowledge on and applications of fructosamine-related molecules in chemistry, food, and health sciences, as reflected mostly in publications within the past decade. Methods of fructosamine synthesis and analysis, its chemical, and biological properties, and degradation reactions, together with fructosamine-modifying and -recognizing proteins are surveyed.</p>","PeriodicalId":448936,"journal":{"name":"Advances in carbohydrate chemistry and biochemistry","volume":"83 ","pages":"27-132"},"PeriodicalIF":0.0,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"134650834","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Preface.","authors":"David C Baker","doi":"10.1016/S0065-2318(23)00027-6","DOIUrl":"10.1016/S0065-2318(23)00027-6","url":null,"abstract":"","PeriodicalId":448936,"journal":{"name":"Advances in carbohydrate chemistry and biochemistry","volume":"84 ","pages":"ix"},"PeriodicalIF":0.0,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"138049135","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Computational modeling of protein-carbohydrate interactions: Current trends and future challenges.","authors":"Serge Pérez","doi":"10.1016/bs.accb.2023.10.003","DOIUrl":"10.1016/bs.accb.2023.10.003","url":null,"abstract":"<p><p>The article leads the reader through an up-to-date presentation of the concepts, developments, and main applications of computational modeling to study protein-carbohydrate interactions. It follows with the presentation of some current issues and perspectives arising from the expected evolution of generic methodological developments in deep learning, immersive analytics, and virtual reality for molecular visualization and data management. Such methodological developments for macromolecular interactions would greatly benefit a wide range of scientific endeavors in the field of carbohydrate chemistry and biochemistry, including the following interrelated efforts dealing with highly crowded media, with examples concerning glycoside transferases, the extracellular matrix, and the exploration of interactions between complex carbohydrates and intrinsically disordered proteins.</p>","PeriodicalId":448936,"journal":{"name":"Advances in carbohydrate chemistry and biochemistry","volume":"83 ","pages":"133-149"},"PeriodicalIF":0.0,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"134650836","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Preface.","authors":"David C Baker","doi":"10.1016/S0065-2318(23)00014-8","DOIUrl":"10.1016/S0065-2318(23)00014-8","url":null,"abstract":"","PeriodicalId":448936,"journal":{"name":"Advances in carbohydrate chemistry and biochemistry","volume":"83 ","pages":"ix-x"},"PeriodicalIF":0.0,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"134650837","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Tarun K Dam, Olivia Hohman, Lucas Sheppard, C Fred Brewer, Purnima Bandyopadhyay
{"title":"Mechanism of multivalent glycoconjugate-lectin interaction: An update.","authors":"Tarun K Dam, Olivia Hohman, Lucas Sheppard, C Fred Brewer, Purnima Bandyopadhyay","doi":"10.1016/bs.accb.2023.10.004","DOIUrl":"10.1016/bs.accb.2023.10.004","url":null,"abstract":"<p><p>Lectins are predominantly oligomeric proteins with several binding sites per molecule. Glycoconjugates are their natural ligands, which often possess multiple binding epitopes. Thus, lectin-glycoconjugate interactions are mostly multivalent in nature. The mechanism of multivalent binding is fundamentally different from those described for monovalent interactions in textbooks and research papers. Over the years, binding studies that make use of different lectins and a variety of multivalent glycoconjugate ligands were conducted in order to understand the underlying principles of multivalency. Starting with seemingly simple synthetic multivalent analogs, systematic studies were carried out using natural glycoconjugate ligands with increasing valency and complexity. Those ligands included multivalent glycoproteins, polyvalent polysaccharides, including glycosaminoglycans, as well as supra-valent mucins and proteoglycans. Models and mechanisms of multivalent binding derived from quantitative data are summarized in the present updated review.</p>","PeriodicalId":448936,"journal":{"name":"Advances in carbohydrate chemistry and biochemistry","volume":"84 ","pages":"1-21"},"PeriodicalIF":0.0,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"138049133","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Multivalent lectin-carbohydrate interactions: Energetics and mechanisms of binding.","authors":"Tarun K Dam, C Fred Brewer","doi":"10.1016/bs.accb.2023.10.005","DOIUrl":"10.1016/bs.accb.2023.10.005","url":null,"abstract":"<p><p>The biological signaling properties of lectins, which are carbohydrate-binding proteins, are due to their ability to bind and cross-link multivalent glycoprotein receptors on the surface of normal and transformed cells. While the cross-linking properties of lectins with multivalent carbohydrates and glycoproteins are relatively well understood, the mechanisms of binding of lectins to multivalent glycoconjugates are less well understood. Recently, the thermodynamics of binding of lectins to synthetic clustered glycosides, a multivalent globular glycoprotein, and to linear glycoproteins (mucins) have been described. The results are consistent with a dynamic binding mechanism in which lectins bind and jump from carbohydrate to carbohydrate epitope in these molecules. Importantly, the mechanism of binding of lectins to mucins is similar to that for a variety of protein ligands binding to DNA. Recent analysis also shows that high-affinity lectin-mucin cross-linking interactions are driven by favorable entropy of binding that is associated with the bind and jump mechanism. The results suggest that the binding of ligands to biopolymers, in general, may involve a common mechanism that involves enhanced entropic effects which facilitate binding and subsequent complex formation including enzymology.</p>","PeriodicalId":448936,"journal":{"name":"Advances in carbohydrate chemistry and biochemistry","volume":"84 ","pages":"23-48"},"PeriodicalIF":0.0,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"138049134","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"1-Amino-1-deoxy-d-fructose (\"fructosamine\") and its derivatives: An update.","authors":"Valeri V Mossine, Thomas P Mawhinney","doi":"10.1016/bs.accb.2023.10.001","DOIUrl":"10.1016/bs.accb.2023.10.001","url":null,"abstract":"<p><p>1-Amino-1-deoxy-d-fructose (fructosamine, FN) derivatives are omnipresent in all living organisms, as a result of non-enzymatic condensation and Amadori rearrangement reactions between free glucose and biogenic amines such as amino acids, polypeptides, or aminophospholipids. Over decades, steady interest in fructosamine was largely sustained by its role as a key intermediate structure in the Maillard reaction that is responsible for the organoleptic and nutritional value of thermally processed foods, and for pathophysiological effects of hyperglycemia in diabetes. New trends in fructosamine research include the discovery and engineering of FN-processing enzymes, development of advanced tools for hyperglycemia monitoring, and evaluation of the therapeutic potential of both fructosamines and FN-recognizing proteins. This article covers developments in the field of fructosamine and its derivatives since 2010 and attempts to ascertain challenges in future research.</p>","PeriodicalId":448936,"journal":{"name":"Advances in carbohydrate chemistry and biochemistry","volume":"83 ","pages":"1-26"},"PeriodicalIF":0.0,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"134650835","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Carbohydrate-Processing Enzymes of the Lysosome: Diseases Caused by Misfolded Mutants and Sugar Mimetics as Correcting Pharmacological Chaperones.","authors":"Arnold E Stütz, Tanja M Wrodnigg","doi":"10.1016/bs.accb.2016.08.002","DOIUrl":"https://doi.org/10.1016/bs.accb.2016.08.002","url":null,"abstract":"<p><p>Lysosomal storage diseases are hereditary disorders caused by mutations on genes encoding for one of the more than fifty lysosomal enzymes involved in the highly ordered degradation cascades of glycans, glycoconjugates, and other complex biomolecules in the lysosome. Several of these metabolic disorders are associated with the absence or the lack of activity of carbohydrate-processing enzymes in this cell compartment. In a recently introduced therapy concept, for susceptible mutants, small substrate-related molecules (so-called pharmacological chaperones), such as reversible inhibitors of these enzymes, may serve as templates for the correct folding and transport of the respective protein mutant, thus improving its concentration and, consequently, its enzymatic activity in the lysosome. Carbohydrate-processing enzymes in the lysosome, related lysosomal diseases, and the scope and limitations of reported reversible inhibitors as pharmacological chaperones are discussed with a view to possibly extending and improving research efforts in this area of orphan diseases.</p>","PeriodicalId":448936,"journal":{"name":"Advances in carbohydrate chemistry and biochemistry","volume":"73 ","pages":"225-302"},"PeriodicalIF":0.0,"publicationDate":"2016-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144183349","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}