Versatile applications of 3-OxoGlycals: A review
Carbohydr Res. 2023 Dec 23;536:109016. doi: 10.1016/j.carres.2023.109016. Online ahead of print.ABSTRACT3-Oxoglycals are versatile building blocks with extensive applications in glycochemistry, organic, and bio-organic sciences. They serve as powerful synthons, enabling the development of diverse organic structures. This review highlights the utility of easily obtainable 3-oxoglycals as fundamental building blocks for synthesizing various compounds, including rare sugars, N-inserted compounds, fused heterocycles, medium ring compounds, polycyclic molecules, cycloadducts, and axially chiral molecules. Some of these compound...
Source: Carbohydrate Research - January 12, 2024 Category: Genetics & Stem Cells Authors: Sateesh Dubbu Source Type: research
Structure of the O-polysaccharide from the moderately halophilic bacterium Halomonas fontilapidosi KR26
Carbohydr Res. 2023 Dec 30;536:109019. doi: 10.1016/j.carres.2023.109019. Online ahead of print.ABSTRACTLipopolysaccharide was obtained from the aerobic moderately halophilic bacterium Halomonas fontilapidosi KR26. The O-polysaccharide was isolated by mild acid degradation of the lipopolysaccharide and was examined by chemical methods and by 1H and 13C NMR spectroscopy, including 1H,1H COSY, TOCSY, ROESY, and 1H,13C HSQC, and HMBC experiments. The following structure of the linear tetrasaccharide repeating unit was deduced. →2)-α-l-Rhap-(1→2)-α-l-Rhap-(1→3)-α-l-Rhap-(1→3)-β-d-Galp-(1→.PMID:38211449 | DOI:10.1...
Source: Carbohydrate Research - January 11, 2024 Category: Genetics & Stem Cells Authors: Elena N Sigida Marina S Kuzina Maxim S Kokoulin Ibrahim M Ibrahim Vyacheslav S Grinev Svetlana A Konnova Yuliya P Fedonenko Source Type: research
Optimization of preparation conditions of medium and highly substituted carboxymethyl inulin through response surface methodology
This article introduces the synthesis optimization of carboxymethyl inulin using response surface methodology. The important factors affecting the degree of substitution (DS) were determined by Plackett-Burman design, including sodium hydroxide concentration, monochloroacetic concentration, and etherification temperature. Further optimization was conducted using the Box-Behnken response surface design. The coefficient of determination (R2) of the response surface model was 0.9827, and the adjusted R2 value was 0.9516, which proved the significance of the model. The optimized results of the predicted response showed that th...
Source: Carbohydrate Research - January 11, 2024 Category: Genetics & Stem Cells Authors: Dongkui Zhou Weichu Yu Aibin Wu Wenming Shu Ying Zhang Source Type: research
Big is not better: Comparing two alpha-Gal-bearing glycotopes in neoglycoproteins as biomarkers for Leishmania (Viannia) braziliensis infection
Carbohydr Res. 2023 Dec 28;536:109015. doi: 10.1016/j.carres.2023.109015. Online ahead of print.ABSTRACTThe protozoan parasite Leishmania (Viannia) braziliensis is among Latin America's most widespread Leishmania species and is responsible for tegumentary leishmaniasis (TL). This disease has multiple clinical presentations, with cutaneous leishmaniasis (CL) being the most frequent. It manifests as one or a few localized skin ulcers, which can spread to other body areas. Hence, early diagnosis and treatment, typically with pentavalent antimonials, is critical. Traditional diagnostic methods, like parasite culture, microscop...
Source: Carbohydrate Research - January 10, 2024 Category: Genetics & Stem Cells Authors: Alba L Montoya Eileni R Gil Irodiel Vinales Igor L Estevao Paola Taboada Mary Cruz Torrico Faustino Torrico Jorge Diego Marco Igor C Almeida Katja Michael Source Type: research
Synthesis of substituted 2H-Chromenes via Pd-catalyzed C-H activation and thermal cyclization
Carbohydr Res. 2023 Dec 23;536:109018. doi: 10.1016/j.carres.2023.109018. Online ahead of print.ABSTRACTA proficient approach has been developed for the synthesis of substituted 2H-chromenes from C1-substituted glucal. The key step of our synthetic methodology was C-H activation in propylene carbonate solvent followed by 6π-electrocyclization aromatization in ethylene glycol as greener substitutes to toxic aprotic solvents, to obtain 2H-chromenes in a stepwise manner. The application of the developed methodology was further explored with the synthesis of a small library of substituted 2H-chromenes in good yields.PMID:3818...
Source: Carbohydrate Research - January 7, 2024 Category: Genetics & Stem Cells Authors: Vipin K Maikhuri Vineet Verma Divya Mathur Ashok K Prasad Vinod Khatri Source Type: research
Facile synthesis of C5-azido derivatives of thiosialosides and 2,3-dehydro-5-N-acetylneuraminic acid (DANA)
We examined two diazo-transfer strategies and compared their yields and tolerance of acetate protecting groups. The same methods and comparisons were also performed for the 2,3-dehydro-5-N-acetylneuraminic acid (DANA) scaffold which is commonly used to generate inhibitors of neuraminidase (sialidase) enzymes. We found that C5-azido derivatives of both thiosialosides and DANA could be produced in five or six steps with yields up to 76 % and 83 %, respectively. Diazo-transfer reagents compared in this study were trifluoromethanesulfonyl azide (TfN3) and imidazole-1-sulfonyl azide (ImzSO2N3). We found that both reagents were ...
Source: Carbohydrate Research - January 7, 2024 Category: Genetics & Stem Cells Authors: Mostafa Radwan Manas Jana Christopher W Cairo Source Type: research
Synthesis of substituted 2H-Chromenes via Pd-catalyzed C-H activation and thermal cyclization
Carbohydr Res. 2023 Dec 23;536:109018. doi: 10.1016/j.carres.2023.109018. Online ahead of print.ABSTRACTA proficient approach has been developed for the synthesis of substituted 2H-chromenes from C1-substituted glucal. The key step of our synthetic methodology was C-H activation in propylene carbonate solvent followed by 6π-electrocyclization aromatization in ethylene glycol as greener substitutes to toxic aprotic solvents, to obtain 2H-chromenes in a stepwise manner. The application of the developed methodology was further explored with the synthesis of a small library of substituted 2H-chromenes in good yields.PMID:3818...
Source: Carbohydrate Research - January 7, 2024 Category: Genetics & Stem Cells Authors: Vipin K Maikhuri Vineet Verma Divya Mathur Ashok K Prasad Vinod Khatri Source Type: research
Facile synthesis of C5-azido derivatives of thiosialosides and 2,3-dehydro-5-N-acetylneuraminic acid (DANA)
We examined two diazo-transfer strategies and compared their yields and tolerance of acetate protecting groups. The same methods and comparisons were also performed for the 2,3-dehydro-5-N-acetylneuraminic acid (DANA) scaffold which is commonly used to generate inhibitors of neuraminidase (sialidase) enzymes. We found that C5-azido derivatives of both thiosialosides and DANA could be produced in five or six steps with yields up to 76 % and 83 %, respectively. Diazo-transfer reagents compared in this study were trifluoromethanesulfonyl azide (TfN3) and imidazole-1-sulfonyl azide (ImzSO2N3). We found that both reagents were ...
Source: Carbohydrate Research - January 7, 2024 Category: Genetics & Stem Cells Authors: Mostafa Radwan Manas Jana Christopher W Cairo Source Type: research
Synthesis of substituted 2H-Chromenes via Pd-catalyzed C-H activation and thermal cyclization
Carbohydr Res. 2023 Dec 23;536:109018. doi: 10.1016/j.carres.2023.109018. Online ahead of print.ABSTRACTA proficient approach has been developed for the synthesis of substituted 2H-chromenes from C1-substituted glucal. The key step of our synthetic methodology was C-H activation in propylene carbonate solvent followed by 6π-electrocyclization aromatization in ethylene glycol as greener substitutes to toxic aprotic solvents, to obtain 2H-chromenes in a stepwise manner. The application of the developed methodology was further explored with the synthesis of a small library of substituted 2H-chromenes in good yields.PMID:3818...
Source: Carbohydrate Research - January 7, 2024 Category: Genetics & Stem Cells Authors: Vipin K Maikhuri Vineet Verma Divya Mathur Ashok K Prasad Vinod Khatri Source Type: research
Facile synthesis of C5-azido derivatives of thiosialosides and 2,3-dehydro-5-N-acetylneuraminic acid (DANA)
We examined two diazo-transfer strategies and compared their yields and tolerance of acetate protecting groups. The same methods and comparisons were also performed for the 2,3-dehydro-5-N-acetylneuraminic acid (DANA) scaffold which is commonly used to generate inhibitors of neuraminidase (sialidase) enzymes. We found that C5-azido derivatives of both thiosialosides and DANA could be produced in five or six steps with yields up to 76 % and 83 %, respectively. Diazo-transfer reagents compared in this study were trifluoromethanesulfonyl azide (TfN3) and imidazole-1-sulfonyl azide (ImzSO2N3). We found that both reagents were ...
Source: Carbohydrate Research - January 7, 2024 Category: Genetics & Stem Cells Authors: Mostafa Radwan Manas Jana Christopher W Cairo Source Type: research
On the influence of solvent on the stereoselectivity of glycosylation reactions
Carbohydr Res. 2023 Dec 13;535:109010. doi: 10.1016/j.carres.2023.109010. Online ahead of print.ABSTRACTMethodology development in carbohydrate chemistry entails the stereoselective formation of C-O bonds as a key step in the synthesis of oligo- and polysaccharides. The anomeric selectivity of a glycosylation reaction is affected by a multitude of parameters, such as the nature of the donor and acceptor, activator/promotor system, temperature and solvent. The influence of different solvents on the stereoselective outcome of glycosylation reactions employing thioglucopyranosides as glycosyl donors with a non-participating p...
Source: Carbohydrate Research - January 5, 2024 Category: Genetics & Stem Cells Authors: Kevin M Dorst Olof Engstr öm Thibault Angles d'Ortoli Hani Mobarak Azad Ebrahemi Ulf Fagerberg Dennis M Whitfield G öran Widmalm Source Type: research
On the influence of solvent on the stereoselectivity of glycosylation reactions
Carbohydr Res. 2023 Dec 13;535:109010. doi: 10.1016/j.carres.2023.109010. Online ahead of print.ABSTRACTMethodology development in carbohydrate chemistry entails the stereoselective formation of C-O bonds as a key step in the synthesis of oligo- and polysaccharides. The anomeric selectivity of a glycosylation reaction is affected by a multitude of parameters, such as the nature of the donor and acceptor, activator/promotor system, temperature and solvent. The influence of different solvents on the stereoselective outcome of glycosylation reactions employing thioglucopyranosides as glycosyl donors with a non-participating p...
Source: Carbohydrate Research - January 5, 2024 Category: Genetics & Stem Cells Authors: Kevin M Dorst Olof Engstr öm Thibault Angles d'Ortoli Hani Mobarak Azad Ebrahemi Ulf Fagerberg Dennis M Whitfield G öran Widmalm Source Type: research
On the origin of the electronic and magnetic circular dichroism of naphthyl C-glycosides: Anomeric configuration
In conclusion, reliable ECD patterns cannot be calculated by separating the naphthyl rotation from other conformational motions. MCD patterns have been similar for all the naphthyl C-glycosides studied. No clear diagnostic features have been found for either the pseudoanomeric configuration or the preferred hydroxymethyl rotamer. Nevertheless, the work has demonstrated the potential of MCD for the study of aryl glycosides interacting with proteins.PMID:38171193 | DOI:10.1016/j.carres.2023.109021 (Source: Carbohydrate Research)
Source: Carbohydrate Research - January 3, 2024 Category: Genetics & Stem Cells Authors: Jan Choutka Kamil Parkan Radek Pohl Jakub Kaminsk ý Source Type: research
On the origin of the electronic and magnetic circular dichroism of naphthyl C-glycosides: Anomeric configuration
In conclusion, reliable ECD patterns cannot be calculated by separating the naphthyl rotation from other conformational motions. MCD patterns have been similar for all the naphthyl C-glycosides studied. No clear diagnostic features have been found for either the pseudoanomeric configuration or the preferred hydroxymethyl rotamer. Nevertheless, the work has demonstrated the potential of MCD for the study of aryl glycosides interacting with proteins.PMID:38171193 | DOI:10.1016/j.carres.2023.109021 (Source: Carbohydrate Research)
Source: Carbohydrate Research - January 3, 2024 Category: Genetics & Stem Cells Authors: Jan Choutka Kamil Parkan Radek Pohl Jakub Kaminsk ý Source Type: research
Impact of ultrasound treatment on the structural modifications and functionality of carbohydrates - A review
Carbohydr Res. 2023 Dec 21;535:109017. doi: 10.1016/j.carres.2023.109017. Online ahead of print.ABSTRACTCarbohydrates are crucial in food as essential biomolecules, serving as natural components, ingredients, or additives. Carbohydrates have numerous applications in the food industry as stabilizers, thickeners, sweeteners, and humectants. The properties and functionality of the carbohydrates undergo alterations when exposed to various thermal or non-thermal treatments. Ultrasonication is a non-thermal method that modifies the structural arrangement of carbohydrate molecules. These structural changes lead to enhanced gellin...
Source: Carbohydrate Research - January 1, 2024 Category: Genetics & Stem Cells Authors: Nirmal Thirunavookarasu Sumit Kumar Prakyath Shetty Akalya Shanmugam Ashish Rawson Source Type: research
