Like Visiting an Old Friend: Fischer Glycosylation in the Twenty-First Century: Modern Methods and Techniques

Haese, Matteo; Winterhalter, Kai; Jung, Jessica; Schmidt, Magnus S.

doi:10.1007/s41061-022-00383-9

Cited by 4 publications

(2 citation statements)

References 57 publications

(93 reference statements)

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“…Enzyme‐catalyzed transglycosylation to prepare 3 (Scheme S1, Supporting Information) gave α‐(1→6)‐linked J and α‐(1→3)‐linked 3 , which were separated by chromatography on a Sephadex G‐10 column followed by chromatography on a Dowex‐1 × 8 (OH − ) column 65 . Preparation of the glycosyl acceptor, methyl β‐D‐galactopyranoside ( I ), was first attempted by Fischer glycosidation in methanol, 66–68 but gave the α‐pyranoside as the heavily favored product. An alternate pathway through glycosyl bromide G was then adopted that gave I in ~60% yield from D‐galactose E .…”

Section: Resultsmentioning

confidence: 99%

“…[60][61][62][63] Enzyme-catalyzed transglycosylation to prepare 3 (Scheme S1, Supporting Information) gave α-(1!6)linked J and α-(1!3)-linked 3, which were separated by chromatography on a Sephadex G-10 column followed by chromatography on a Dowex-1 Â 8 (OH À ) column. 65 Preparation of the glycosyl acceptor, methyl β-Dgalactopyranoside (I), was first attempted by Fischer glycosidation in methanol, [66][67][68] but gave the α-pyranoside as the heavily favored product. An alternate pathway through glycosyl bromide G was then adopted that gave I in $60% yield from D-galactose E. Considering the reaction yield to prepare donor D, the reaction regiochemistry that often produces more than one linkage, and the need for excess acceptor (which may preclude isotopic labeling of this component), enzyme-catalyzed transglycosylation will not be a generally useful method to prepare 13 C-labeled disaccharides, although it has the advantage of simplicity.…”

Section: Preparation Of Unlabeled and 13 Clabeled 3 Andmentioning

confidence: 99%

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Methyl α‐D‐galactopyranosyl‐(1→3)‐β‐D‐galactopyranoside and methyl β‐D‐galactopyranosyl‐(1→3)‐β‐D‐galactopyranoside: Glycosidic linkage conformation determined from MA'AT analysis

Meredith,

Zhu,

Yoon

et al. 2024

Magnetic Reson in Chemistry

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MA'AT analysis has been applied to two biologically‐important O‐glycosidic linkages in two disaccharides, α‐D‐Galp‐(1→3)‐β‐D‐GalpOMe (3) and β‐D‐Galp‐(1→3)‐β‐D‐GalpOMe (4). Using density functional theory (DFT) to obtain parameterized equations relating a group of trans‐O‐glycosidic NMR spin‐couplings to either phi (ϕ') or psi (ψ'), and experimental 3JCOCH, 2JCOC, and 3JCOCC spin‐couplings measured in aqueous solution in 13C‐labeled isotopomers, probability distributions of ϕ' and ψ' in each linkage were determined and compared to those determined by aqueous 1‐μs molecular dynamics (MD) simulation. Good agreement was found between the MA'AT and single‐state MD conformational models of these linkages for the most part, with modest (approximately <15°) differences in the mean values of ϕ' and ψ', although the envelope of allowed angles (encoded in circular standard deviations or CSDs) is consistently larger for ϕ' determined from MA'AT analysis than from MD for both linkages. The MA'AT model of the α‐Galp‐(1→3)‐β‐Galp linkage agrees well with those determined previously using conventional NMR methods (3JCOCH values and/or 1H‐1H NOEs), but some discrepancy was observed for the β‐Galp‐(1→3)‐β‐Galp linkage, which may arise from errors in the conventions used to describe the linkage torsion angles. Statistical analyses of X‐ray crystal structures show ranges of ϕ' and ψ' for both linkages that include the mean angles determined from MA'AT analyses, although both angles adopt a wide range of values in the crystalline state, with ϕ' in β‐Galp‐(1→3)‐β‐Galp linkages showing greater‐than‐expected conformational variability.

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Section: Resultsmentioning

confidence: 99%

Section: Preparation Of Unlabeled and 13 Clabeled 3 Andmentioning

confidence: 99%

Methyl α‐D‐galactopyranosyl‐(1→3)‐β‐D‐galactopyranoside and methyl β‐D‐galactopyranosyl‐(1→3)‐β‐D‐galactopyranoside: Glycosidic linkage conformation determined from MA'AT analysis

Meredith,

Zhu,

Yoon

et al. 2024

Magnetic Reson in Chemistry

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Surfactants produced from carbohydrate derivatives: Part 2. A review on the value chain, synthesis, and the potential role of artificial intelligence within the biorefinery concept

Marquez,

Ortiz,

Barrios

et al. 2024

J Surfact & Detergents

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This comprehensive and critical review explores the synthesis and applications of carbohydrate‐based surfactants within the biorefinery concept, focusing on biobased sugar‐head molecules suitable for use across several manufacturing sectors, including cosmetics, pharmaceuticals, household products, detergents, and foods. The main focus relies on sustainable alternatives to conventional surfactants, which could reduce the final manufacturing carbon footprint of several industrial feedstocks and products. A thorough analysis of raw materials, highlighting the significance of feedstock sources, and the current biobased surfactants and rhamnolipid biosurfactants production trends, is presented. Key organic reactions for the production of sorbitan esters, sucrose esters, alkyl polyglycosides, and fatty acid glucamines, such as glycosidation, acylation, and etherification, as well as the production of rhamnolipids through fermentation are described. Given the scarce literature on the characterization of these surfactant types within the hydrophilic–lipophilic deviation (HLD) framework, the surfactant contribution parameter (SCP) in the HLD equation for sugar‐head surfactants is critically assessed. The economic landscape is also discussed, noting the significant growth in the biobased surfactants and biosurfactant market, driven by environmental awareness and regulatory changes, with projections indicating a substantial market increase in the forthcoming years. Finally, the promising potential of generative artificial intelligence (AI) in developing customized surfactant molecules, with optimized properties for targeted applications, is emphasized as a promising avenue for future research.

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Unveiling the role of the ring size in the sugar-based tensides surfactancy by interfacial studies and molecular dynamics

Sangiorgio,

Pargoletti,

Ballabio

et al. 2024

Journal of Molecular Liquids

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Like Visiting an Old Friend: Fischer Glycosylation in the Twenty-First Century: Modern Methods and Techniques

Cited by 4 publications

References 57 publications

Methyl α‐D‐galactopyranosyl‐(1→3)‐β‐D‐galactopyranoside and methyl β‐D‐galactopyranosyl‐(1→3)‐β‐D‐galactopyranoside: Glycosidic linkage conformation determined from MA'AT analysis

Methyl α‐D‐galactopyranosyl‐(1→3)‐β‐D‐galactopyranoside and methyl β‐D‐galactopyranosyl‐(1→3)‐β‐D‐galactopyranoside: Glycosidic linkage conformation determined from MA'AT analysis

Surfactants produced from carbohydrate derivatives: Part 2. A review on the value chain, synthesis, and the potential role of artificial intelligence within the biorefinery concept

Unveiling the role of the ring size in the sugar-based tensides surfactancy by interfacial studies and molecular dynamics

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