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Journal of the American Chemical Society Mar 2019The translation of biological glycosylation in humans to the clinical applications involves systematic studies using homogeneous samples of oligosaccharides and... (Review)
Review
The translation of biological glycosylation in humans to the clinical applications involves systematic studies using homogeneous samples of oligosaccharides and glycoconjugates, which could be accessed by chemical, enzymatic or other biological methods. However, the structural complexity and wide-range variations of glycans and their conjugates represent a major challenge in the synthesis of this class of biomolecules. To help navigate within many methods of oligosaccharide synthesis, this Perspective offers a critical assessment of the most promising synthetic strategies with an eye on the therapeutically relevant targets.
Topics: Glycosylation; Humans; Molecular Structure; Oligosaccharides
PubMed: 30716271
DOI: 10.1021/jacs.8b11005 -
Chemical Society Reviews Jan 2008Peptides and oligonucleotides are prepared by automated synthesizers that can be operated by non-specialists. Carbohydrates have been hard to assemble, but the... (Review)
Review
Peptides and oligonucleotides are prepared by automated synthesizers that can be operated by non-specialists. Carbohydrates have been hard to assemble, but the increasing awareness of the biological importance of this class of complex repeating biopolymers has prompted efforts to accelerate their synthesis. This tutorial review defines the state of the art of automated solid phase oligosaccharide synthesis and identifies areas in need of further innovation. Application of the automated synthesis method to prepare a malaria vaccine candidate is briefly highlighted.
Topics: Automation; Carbohydrate Conformation; Carbohydrate Sequence; Malaria Vaccines; Molecular Sequence Data; Oligosaccharides
PubMed: 18197330
DOI: 10.1039/b511197h -
Natural Product Reports Aug 2014Covering up to December 2013. Oligosaccharide natural products target a wide spectrum of biological processes including disruption of cell wall biosynthesis,... (Review)
Review
Covering up to December 2013. Oligosaccharide natural products target a wide spectrum of biological processes including disruption of cell wall biosynthesis, interference of bacterial translation, and inhibition of human α-amylase. Correspondingly, oligosaccharides possess the potential for development as treatments of such diverse diseases as bacterial infections and type II diabetes. Despite their potent and selective activities and potential clinical relevance, isolated bioactive secondary metabolic oligosaccharides are less prevalent than other classes of natural products and their biosynthesis has received comparatively less attention. This review highlights the unique modes of action and biosynthesis of four classes of bioactive oligosaccharides: the orthosomycins, moenomycins, saccharomicins, and acarviostatins.
Topics: Anti-Bacterial Agents; Biological Products; Humans; Molecular Structure; Oligosaccharides; alpha-Amylases
PubMed: 24883430
DOI: 10.1039/c3np70128j -
Chemical Reviews Sep 2018Catalytic glycosylation has been a central reaction in carbohydrate chemistry since its introduction by Fischer 125 years ago, but it is only in the past three to four... (Review)
Review
Catalytic glycosylation has been a central reaction in carbohydrate chemistry since its introduction by Fischer 125 years ago, but it is only in the past three to four decades that catalytic methods for synthesizing oligosaccharides have appeared. Despite the development of numerous elegant and ingenious catalytic glycosylation methods, only a few are in general use. This review covers all methods of catalytic glycosylation with the focus on the development and application in oligosaccharide synthesis and provide an overview of the scope and limitations of these. The review also includes relevant mechanistic studies of catalytic glycosylations. The future of catalytic glycosylation chemistry is discussed, including specific, upcoming methods and possible directions for the field of research in general.
Topics: Carbohydrate Sequence; Catalysis; Chemistry Techniques, Synthetic; Glycosylation; Oligosaccharides; Stereoisomerism
PubMed: 29969248
DOI: 10.1021/acs.chemrev.8b00144 -
Nutrients Nov 2019Human milk oligosaccharides have been recognized as an important, functional biomolecule in mothers' milk. Moreover, these oligosaccharides have been recognized as the... (Review)
Review
Human milk oligosaccharides have been recognized as an important, functional biomolecule in mothers' milk. Moreover, these oligosaccharides have been recognized as the third most abundant component of human milk, ranging from 10-15 g/L in mature milk and up to and over 20 g/L reported in colostrum. Initially, health benefits of human milk oligosaccharides were assigned via observational studies on the differences between breastfed and bottle fed infants. Later, pools of milk oligosaccharides were isolated and used in functional studies and in recent years more specific studies into structure-function relationships have identified some advanced roles for milk oligosaccharides in the healthy development of infants. In other research, the levels, diversity, and complexity of human milk oligosaccharides have been studied, showing a wide variation in results. This review gives a critical overview of challenges in the analysis of human milk oligosaccharides. In view of the myriad functions that can be assigned, often to specific structures or classes of structures, it is very relevant to assess the levels of these structures in the human milk correctly, as well as in other biological sample materials. Ultimately, the review makes a case for a comparative, inter-laboratory study on quantitative human milk oligosaccharide analysis in all relevant biological samples.
Topics: Chromatography, Ion Exchange; Humans; Infant; Mass Spectrometry; Milk, Human; Oligosaccharides
PubMed: 31698698
DOI: 10.3390/nu11112684 -
Nutrients Mar 2021Human milk oligosaccharides (HMOs) are complex unconjugated glycans associated with positive infant health outcomes. This study has examined current knowledge of the... (Review)
Review
Human milk oligosaccharides (HMOs) are complex unconjugated glycans associated with positive infant health outcomes. This study has examined current knowledge of the effect of maternal diet and nutritional status on the composition of HMOs in breast milk. Using the PRISMA-ScR guidelines, a comprehensive, systematic literature search was conducted using Scopus, Web of Science, Global Health (CABI), and MEDLINE. Titles and abstracts were screened independently by two reviewers against predefined inclusion and exclusion criteria. Fourteen studies met the inclusion criteria and reported on maternal dietary intake ( = 3), maternal body composition indices ( = 9), and dietary supplementation interventions ( = 2). In total, data from 1388 lactating mothers (4011 milk samples) were included. Design methodologies varied substantially across studies, particularly for milk sample collection, HMO analysis, dietary and body composition assessment. Overall, this review has identified potential associations between maternal dietary intake and nutritional status and the HMO composition of human milk, though an abundance and sufficiency of evidence is lacking. Standardised procedures for human milk sample collection and HMO analysis, along with robust and validated nutrition assessment techniques, should be employed to further investigate the impact of maternal nutritional factors on HMO composition.
Topics: Female; Humans; Maternal Nutritional Physiological Phenomena; Milk, Human; Oligosaccharides
PubMed: 33802639
DOI: 10.3390/nu13030965 -
Organic & Biomolecular Chemistry Jul 2007Saccharide synthesis is a formidable task for synthetic chemists. Although in recent years many advances have been made in this area, development of more convenient and... (Review)
Review
Saccharide synthesis is a formidable task for synthetic chemists. Although in recent years many advances have been made in this area, development of more convenient and efficient strategies for oligosaccharide synthesis is still in great demand. This review focuses on one of these new strategies--the one-pot sequential glycosylation approach as a potent tool for oligosaccharide assembly.
Topics: Carbohydrate Conformation; Carbohydrate Sequence; Combinatorial Chemistry Techniques; Glycosylation; Molecular Sequence Data; Oligosaccharides
PubMed: 17609746
DOI: 10.1039/b704586g -
Chemical Reviews Sep 2018Advances in carbohydrate chemistry have certainly made common oligosaccharides much more accessible. However, many current methods still rely heavily upon specialized... (Review)
Review
Advances in carbohydrate chemistry have certainly made common oligosaccharides much more accessible. However, many current methods still rely heavily upon specialized knowledge of carbohydrate chemistry. The application of automated technologies to chemical and life science applications such as genomics and proteomics represents a vibrant field. These automated technologies also present opportunities for their application to organic synthesis, including that of the synthesis of oligosaccharides. However, application of automated methods to the synthesis of carbohydrates is an underdeveloped area as compared to other classes of biomolecules. The overarching goal of this review article is to present the advances that have been made at the interface of carbohydrate chemistry and automated technology.
Topics: Automation; Carbohydrate Sequence; Chemistry Techniques, Synthetic; Glycosylation; Oligosaccharides
PubMed: 29953217
DOI: 10.1021/acs.chemrev.8b00051 -
Advances in Carbohydrate Chemistry and... 2009
Review
Topics: Carbohydrate Sequence; Enzymes; Glycosylation; Molecular Sequence Data; Oligosaccharides; Stereoisomerism; Substrate Specificity; Time Factors
PubMed: 19501706
DOI: 10.1016/S0065-2318(09)00005-5 -
Angewandte Chemie (International Ed. in... Dec 2011Carbohydrates have been shown to play important roles in biological processes. The pace of development in carbohydrate research is, however, relatively slow due to the... (Review)
Review
Carbohydrates have been shown to play important roles in biological processes. The pace of development in carbohydrate research is, however, relatively slow due to the problems associated with the complexity of carbohydrate structures and the lack of general synthetic methods and tools available for the study of this class of biomolecules. Recent advances in synthesis have demonstrated that many of these problems can be circumvented. In this Review, we describe the methods developed to tackle the problems of carbohydrate-mediated biological processes, with particular focus on the issue related to the development of the automated synthesis of oligosaccharides. Further applications of carbohydrate microarrays and vaccines to human diseases are also highlighted.
Topics: Animals; Carbohydrate Sequence; Carbohydrates; Humans; Oligosaccharides; Vaccines
PubMed: 22127846
DOI: 10.1002/anie.201100125