Glycosyltransferases: glycoengineers in human milk oligosaccharide synthesis and manufacturing

Frontiers in Molecular Biosciences, Год журнала: 2025, Номер 12

Опубликована: Апрель 30, 2025

Human milk oligosaccharides (HMOs) are a diverse group of complex carbohydrates that play crucial roles in infant health, promoting beneficial gut microbiota, modulating immune responses, and protecting against pathogens. Central to the synthesis HMOs glycosyltransferases, specialized class enzymes catalyse transfer sugar moieties form glycan structures characteristic HMOs. This review provides an in-depth analysis beginning with their classification based on structural functional characteristics. The catalytic activity these is explored, highlighting mechanisms by which they facilitate precise addition monosaccharides HMO biosynthesis. Structural insights into glycosyltransferases also discussed, shedding light how conformational features enable specific glycosidic bond formations. maps out key biosynthetic pathways involved production, including lactose, subsequent fucosylation sialylation processes, all intricately regulated glycosyltransferases. Industrial methods for synthesis, chemical, enzymatic, microbial approaches, examined, emphasizing role processes. Finally, discusses future directions glycosyltransferase research, particularly enhancing efficiency developing advanced analytical techniques better understand complexity biological functions

Язык: Английский

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Selective Acetylation of Unprotected Thioglycosides and Fully Unprotected Monosaccharides with Candida antarctica Lipase-B

ACS Omega, Год журнала: 2025, Номер 10(19), С. 20047 - 20053

Опубликована: Май 7, 2025

A selective enzymatic acetylation method for the protection of second and sixth positions thio-d-galactopyranoside was found using immobilized Candida antarctica lipase-B (CAL-B). Unfortunately, it determined that enzyme cannot be recycled effectively. The optimized screened with different thioglycosides fully unprotected saccharides. New methods several new partially protected saccharides were found, while synthesis some known saccharides, e.g., third position-protected d-glucose or fourth l-rhamnose, improved. Furthermore, an acetal formation between discovered. main limitation reactions CAL-B has been to substrate solubility.

Язык: Английский

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More than a protective group: 4-methoxyphenyl as a new Janus aglycone

Carbohydrate Research, Год журнала: 2025, Номер 554, С. 109544 - 109544

Опубликована: Май 22, 2025

Язык: Английский

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Synthesis of the pyruvic acid acetal containing tetrasaccharide repeating unit corresponding to the K82 capsular polysaccharide of Acinetobacter baumannii LUH5534 strain

Carbohydrate Research, Год журнала: 2024, Номер 544, С. 109249 - 109249

Опубликована: Авг. 24, 2024

Язык: Английский

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Physicochemical investigations on molecular interactions of adenine with aqueous d-Glucose/d-Maltose solvent media at varying temperatures and compositions

The Journal of Chemical Thermodynamics, Год журнала: 2024, Номер 201, С. 107399 - 107399

Опубликована: Окт. 18, 2024

Язык: Английский

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Convergent Synthesis of the Nonreducing Hexasaccharide Fragment and the Dodecasaccharide Scaffold of Marine Lipopolysaccharide Axinelloside A

Chemistry - A European Journal, Год журнала: 2024, Номер 30(18)

Опубликована: Янв. 23, 2024

Abstract A convergent synthesis of the dodecasaccharide scaffold axinelloside was achieved through Au(I)‐catalyzed [6+6] glycosylation. The initially devised [3+1+2] assembly nonreducing hexasaccharide fragment low‐yielding, whereas a [3+3] glycosylation under Au(I) catalysis proven feasible, allowing for semi‐gram scale preparation wanted hexasaccharide. requisite 1,2‐ cis glycosidic bonds were forged in highly stereoselective fashion by virtue remote acetyl group participation, and judicious manipulation protecting groups. synthetic has been properly protected downstream elaboration toward its natural form.

Язык: Английский

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Unraveling chemical glycosylation: DFT insights into factors imparting stereoselectivity

Green Synthesis and Catalysis, Год журнала: 2024, Номер unknown

Опубликована: Март 1, 2024

Stereoselective chemical glycosylation reactions are pivotal for preparing manifold biologically and medically important compounds, while mechanisms of remain obscure largely speculative. Herein, we performed DFT calculations to delve into the multifaceted mechanistic details reactions, including equilibria among reactive glycosyl triflate intermediates in solution, stereoselectivity imparting protecting groups, solvent effects, base, anomeric effect. Our results provided theoretical corroborations 2-OAc neighbouring group participation (NGP), arming/disarming effect, coordination theory effect on stereochemistry, influence polarity reaction kinetics spanning SN1-SN2 continuum. For first time, existence putative contact-ion-pairs (CIP) oxocarbenium anion organic solutions was theoretically confirmed with identification multiple ground state structures employing an implicit Solvation Model based Density (SMD). Kinetics nucleophilic attack model glucosyl triflates by simple alcohol acceptors ethanol (EtOH) trifluoroethanol (TFE), complexed 2,4,6-tri-tert-butylpyrimidine (TTBP) were explored, revealing essential role close accompanying base rendering glycosidic bond formation thermodynamically favorable. work deepens comprehension mechanism, paving way rational design future advancement efficient environmentally friendly stereoselective reactions.

Язык: Английский

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Convergent Synthesis of a Pentasaccharide Containing a Rare Sugar 4‐amino‐4‐deoxy‐D‐fucose Related to the Cell Wall O‐polysaccharide of Acinetobacter baumannii 90

ChemistrySelect, Год журнала: 2024, Номер 9(17)

Опубликована: Май 2, 2024

Abstract A convenient synthetic strategy has been developed for the synthesis of a pentasaccharide related to cell wall O ‐polysaccharide Acinetobacter baumannii ( A. ) 90 in very good yield applying stereoselective [3+2] block glycosylation reaction. The target was challenging due presence rare sugar, 4‐amino‐4‐deoxy‐D‐fucose and several α‐glycosidic linkages it. construction 1,2‐ cis glycosyl were achieved using combination copper(II) bromide tetra‐ n ‐butylammonium (TBAB) or N ‐iodosuccinimide (NIS) trimethylsilyl trifluoromethanesulfonate (TMSOTf) as thiophilic activator. Perchloric acid supported over silica (HClO 4 ‐SiO 2 mediated orthogonal reaction carried out trichloroacetimidate derivative donor thioglycoside acceptor.

Язык: Английский

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Esterification and Etherification of Aliphatic Alcohols Enabled by Catalytic Strain-Release of Donor–Acceptor Cyclopropane

Organic Letters, Год журнала: 2024, Номер 26(23), С. 4986 - 4991

Опубликована: Июнь 6, 2024

We herein disclose a highly efficient protocol for the esterification and etherification of alcohols, leveraging Sc(OTf)3-catalyzed ring-strain release event in meticulously designed, chromatographically stable mixed anhydrides or benzyl esters that incorporate an intramolecular donor–acceptor cyclopropane (DAC). This versatile method facilitates straightforward functionalization sugar, terpene, steroid alcohols under mild acidic conditions, as showcased by single-catalyst-driven, dual protection sugar diol.

Язык: Английский

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Pectin oligosaccharides from Citri Reticulatae Pericarpium ‘Chachi’ promote wound healing in HaCaT keratinocytes by enhancing cell proliferation and migration

Food Hydrocolloids for Health, Год журнала: 2024, Номер 6, С. 100185 - 100185

Опубликована: Ноя. 9, 2024

Язык: Английский

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