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Journal of Animal Science Feb 2022A completely randomized design employing a 2 × 2 factorial experiment was designed in this study to evaluate the effects of in ovo injection of disaccharide (DS)...
A completely randomized design employing a 2 × 2 factorial experiment was designed in this study to evaluate the effects of in ovo injection of disaccharide (DS) and/or methionine (Met) on hatchability, growth performance, blood hematology, and serum antioxidant parameters in geese. A total of 600 fertilized geese's eggs containing live embryo were randomly assigned into 4 groups with 6 replicates and 25 eggs per replicate. Factors in four groups comprised noninjection, DS injection (25 g/L maltose + 25 g/L sucrose + 7.5 g/L NaCl), Met injection (5 g/L Met + 7.5 g/L NaCl), or DS plus Met injection (25 g/L maltose + 25 g/L sucrose + 5 g/L Met + 7.5 g/L NaCl), respectively. We found that the administration of DS in embryo increased hatching time, yolk sac-free carcass weight, yolk sac-free carcass indexes and decreased assisted hatching ratio, yolk sac weight, yolk sac indexes, but did not affect hatchability and mortality. Moreover, higher body weight and serum glucose concentrations in DS injection group compared with noninjection group were observed on day of hatching. The body weight and average daily gain (ADG) of geese in DS injection group were higher than noninjection group after incubation. In ovo injection of Met increased hatching time and yolk sac-free carcass indexes, but decreased yolk sac indexes. In addition, the strategy of in ovo feeding of Met led to higher body weight, ADG, serum uric acid, glutathione (GSH), and glutathione peroxidase concentrations, as well as lower GSSG/GSH ratio, serum glutathione disulfide (GSSG), and malondialdehyde (MDA) concentrations than the noninjection group on day of hatching. The post-hatching body weight, ADG, serum total protein, albumin, and uric acid concentrations increased, whereas post-hatching serum GSSG and MDA concentrations and GSSG/GSH ratio decreased when injected with Met. In addition, synergistic effects of in ovo injection of DS plus Met on hatching time as well as post-hatching body weight and ADG were observed. Therefore, in ovo injection of DS plus Met was demonstrated to be a way to improve the development of geese during early incubation stages.
Topics: Animals; Antioxidants; Chickens; Disaccharides; Geese; Hematology; Methionine; Ovum; Uric Acid
PubMed: 35094079
DOI: 10.1093/jas/skac014 -
Microbial Physiology 2021Escherichia coli is unable to grow on polymeric and oligomeric chitin, but grows on chitin disaccharide (GlcNAc-GlcNAc; N,N'-diacetylchitobiose) and chitin trisaccharide...
Escherichia coli is unable to grow on polymeric and oligomeric chitin, but grows on chitin disaccharide (GlcNAc-GlcNAc; N,N'-diacetylchitobiose) and chitin trisaccharide (GlcNAc-GlcNAc-GlcNAc; N,N',N''-triacetylchitotriose) via expression of the chb operon (chbBCARFG). The phosphotransferase system (PTS) transporter ChbBCA facilitates transport of both saccharides across the inner membrane and their concomitant phosphorylation at the non-reducing end, intracellularly yielding GlcNAc 6-phosphate-GlcNAc (GlcNAc6P-GlcNAc) and GlcNAc6P-GlcNAc-GlcNAc, respectively. We revisited the intracellular catabolism of the PTS products, thereby correcting the reported functions of the 6-phospho-glycosidase ChbF, the monodeacetylase ChbG, and the transcriptional regulator ChbR. Intracellular accumulation of glucosamine 6P-GlcNAc (GlcN6P-GlcNAc) and GlcN6P-GlcNAc-GlcNAc in a chbF mutant unraveled a role for ChbG as a monodeacetylase that removes the N-acetyl group at the non-reducing end. Consequently, GlcN6P- but not GlcNAc6P-containing saccharides likely function as coactivators of ChbR. Furthermore, ChbF removed the GlcN6P from the non-reducing terminus of the former saccharides, thereby degrading the inducers of the chb operon and facilitating growth on the saccharides. Consequently, ChbF was unable to hydrolyze GlcNAc6P-residues from the non-reducing end, contrary to previous assumptions but in agreement with structural modeling data and with the unusual catalytic mechanism of the family 4 of glycosidases, to which ChbF belongs. We also refuted the assumption that ChiA is a bifunctional endochitinase/lysozyme ChiA, and show that it is unable to degrade peptidoglycans but acts as a bona fide chitinase in vitro and in vivo, enabling growth of E. coli on chitin oligosaccharides when ectopically expressed. Overall, this study revises our understanding of the chitin, chitin oligosaccharide, and chitin disaccharide metabolism of E. coli.
Topics: Chitin; Disaccharides; Escherichia coli; Oligosaccharides; Operon
PubMed: 33794535
DOI: 10.1159/000515178 -
Organic Letters Jun 2023The ezomycins make up a class of complex nucleoside antibiotics that share a common disaccharide core. Herein we present an efficient synthesis of this core from...
The ezomycins make up a class of complex nucleoside antibiotics that share a common disaccharide core. Herein we present an efficient synthesis of this core from diacetone-d-allose, using a ruthenium-catalyzed asymmetric allylic etherification and a carbohydrate synthesis based on the diastereoselective Henry reaction. Our strategy overcomes several challenges, such as introducing a dense array of functional groups and creating consecutive stereocenters with high selectivity. This approach enables the rapid preparation of disaccharides and paves the way for the total synthesis of ezomycins.
Topics: Nucleosides; Disaccharides; Aminoglycosides; Anti-Bacterial Agents
PubMed: 37267119
DOI: 10.1021/acs.orglett.3c01494 -
Molecules (Basel, Switzerland) Nov 2018The enzyme heparanase, an endo-β-glucuronidase, degrades heparan sulfate (HS) chains on the cell surface and in the extracellular matrix. Heparanase regulates numerous... (Review)
Review
The enzyme heparanase, an endo-β-glucuronidase, degrades heparan sulfate (HS) chains on the cell surface and in the extracellular matrix. Heparanase regulates numerous biological processes that drive tumour growth, metastasis and angiogenesis. In addition to its key role in cancer progression, it has also been implicated in an ever-growing number of other diseases, particularly those associated with inflammation. The importance of heparanase in biology has led to numerous efforts over the years to develop assays to monitor its activity and to screen for new inhibitors as potential drug candidates. Despite these efforts and the commercialization of a few kits, most heparanase assays are still complex, labour intensive, costly or have limited application. Herein we review the various methods for assaying heparanase enzymatic activity, focusing on recent developments towards new assays that hold the promise of accelerating research into this important enzyme.
Topics: Animals; Disaccharides; Enzyme Activation; Enzyme Assays; Glucuronidase; Heparitin Sulfate; Humans; Substrate Specificity
PubMed: 30441818
DOI: 10.3390/molecules23112971 -
PloS One 2019Certain bacterial species target the polysaccharide glycosaminoglycans (GAGs) of animal extracellular matrices for colonization and/or infection. GAGs such as hyaluronan...
Certain bacterial species target the polysaccharide glycosaminoglycans (GAGs) of animal extracellular matrices for colonization and/or infection. GAGs such as hyaluronan and chondroitin sulfate consist of repeating disaccharide units of uronate and amino sugar residues, and are depolymerized to unsaturated disaccharides by bacterial extracellular or cell-surface polysaccharide lyase. The disaccharides are degraded and metabolized by cytoplasmic enzymes such as unsaturated glucuronyl hydrolase, isomerase, and reductase. The genes encoding these enzymes are assembled to form a GAG genetic cluster. Here, we demonstrate the Streptococcus agalactiae phosphotransferase system (PTS) for import of unsaturated hyaluronan disaccharide. S. agalactiae NEM316 was found to depolymerize and assimilate hyaluronan, whereas its mutant with a disruption in the PTS genes included in the GAG cluster was unable to grow on hyaluronan, while retaining the ability to depolymerize hyaluronan. Using toluene-treated wild-type cells, the PTS activity for import of unsaturated hyaluronan disaccharide was significantly higher than that observed in the absence of the substrate. In contrast, the PTS mutant was unable to import unsaturated hyaluronan disaccharide, indicating that the corresponding PTS is the only importer of fragmented hyaluronan, which is suitable for PTS to phosphorylate the substrate at the C-6 position. This is distinct from Streptobacillus moniliformis ATP-binding cassette transporter for import of sulfated and non-sulfated fragmented GAGs without substrate modification. The three-dimensional structure of streptococcal EIIA, one of the PTS components, was found to contain a Rossman-fold motif by X-ray crystallization. Docking of EIIA with another component EIIB by modeling provided structural insights into the phosphate transfer mechanism. This study is the first to identify the substrate (unsaturated hyaluronan disaccharide) recognized and imported by the streptococcal PTS. The PTS and ABC transporter for import of GAGs shed light on bacterial clever colonization/infection system targeting various animal polysaccharides.
Topics: Amino Acid Sequence; Disaccharides; Escherichia coli; Extracellular Matrix; Hyaluronic Acid; Models, Biological; Models, Molecular; Phosphotransferases; Streptococcus
PubMed: 31697725
DOI: 10.1371/journal.pone.0224753 -
International Journal of Biological... Jun 2023High viscous products made with starch are of great scientific interest in the food, pharmaceutical, and cosmetic industries because they can be used to make creams and...
High viscous products made with starch are of great scientific interest in the food, pharmaceutical, and cosmetic industries because they can be used to make creams and gels, as well as functional foods and nutritional products. But, obtaining a good quality highly viscous materials represent a technological challenge. In this present study, the effect of high-pressure treatment at 120 psi for different time interval on the mixture of dry-heated alocasia starch in presence of monosaccharide and disaccharide was studied. A flow measurement test on the samples revealed their shear-thinning behavior. With 15 min of high-pressure processing time, the dry-heated starch and saccharide mixtures displayed the highest viscosity. The dynamic viscoelasticity measurement showed that the storage and loss modulus was enhanced significantly after high-pressure treatment, and all pressure-treated samples showed a gel-like structure (G/>G//). In temperature sweep measurement, the rheological profile of storage modulus, loss modulus, and complex viscosity exhibited a two-stage pattern, i.e., first increased, then decreased, and their values were enhanced significantly after pressure treatment. The resultant highly viscous dry-heated starch and saccharide system have various functionalities in diverse food and pharmaceutical products.
Topics: Starch; Alocasia; Disaccharides; Monosaccharides; Viscosity; Rheology
PubMed: 37119887
DOI: 10.1016/j.ijbiomac.2023.124663 -
Organic Letters Jun 2021Stereoselective reactions at the anomeric carbon constitute the cornerstone of preparative carbohydrate chemistry. Here, we report stereoselective C-arylation and...
Stereoselective reactions at the anomeric carbon constitute the cornerstone of preparative carbohydrate chemistry. Here, we report stereoselective C-arylation and etherification reactions of anomeric trifluoroborates derived from BMIDA esters. These reactions are characterized by high anomeric selectivities for 2-deoxysugars and broad substrate scope (24 examples), including disaccharides and trifluoroborates with free hydroxyl groups. Taken together, this new class of carbohydrate reagents adds the palette of anomeric nucleophile reagents suitable for efficient installation of C-C bonds.
Topics: Borates; Carbon; Disaccharides; Esters; Molecular Structure; Stereoisomerism
PubMed: 34029464
DOI: 10.1021/acs.orglett.1c01035 -
Carbohydrate Polymers Oct 2022Fucosylated chondroitin sulfate (FCS) from sea cucumber Ludwigothurea grisea (FCS) is the first one that reported to bear the di-fucosyl branches. Here we deciphered it...
Fucosylated chondroitin sulfate (FCS) from sea cucumber Ludwigothurea grisea (FCS) is the first one that reported to bear the di-fucosyl branches. Here we deciphered it by analyzing the physicochemical properties and its derivatives. Oligosaccharides prepared by selective cleavage of glycosidic linkages presented the mono-fucose and heterodisaccharide branches in FCS. The disaccharide branch was determined as d-GalNAc-(α1,2)-l-Fuc rather than the di-fucosyl branch, where R1 was 4-mono-O- or 4,6-di-O-sulfation, and R2 was 3-mono-O- or 3,4-di-O-sulfation, respectively. The diversity of sulfation patterns in branches complicated the structure. These results give us a new understanding of FCS and provided a reliable method to decipher the FCS with complex branches. Bioanalysis of chemically modified derivatives showed that modulating the molecular mass could enhance the Xase target selectivity. Side chains conferred the Xase complex inhibition by binding to FIXa with a high affinity. Whether monosaccharide and disaccharide branches have differential effects needs to be further explored.
Topics: Animals; Anticoagulants; Chondroitin Sulfates; Disaccharides; Sea Cucumbers
PubMed: 35868774
DOI: 10.1016/j.carbpol.2022.119826 -
Journal of Pharmaceutical Sciences May 2018Low-molecular-weight heparins (LMWHs) are widely used as clinical anticoagulant drugs. LMWHs are heterogeneous and highly negatively charged glycans prepared by chemical...
Low-molecular-weight heparins (LMWHs) are widely used as clinical anticoagulant drugs. LMWHs are heterogeneous and highly negatively charged glycans prepared by chemical or enzymatic depolymerization of unfractionated heparin. The detailed structural analysis of a LMWH is essential for the drug quality control. In this study, an LMWH, enoxaparin sodium (a generic version of Lovenox) was separated into different molecular weight fractions by a Superdex peptide column. The disaccharide compositions, 3-O-sulfo group-containing tetrasaccharides composition, and antithrombin III-binding affinity of the fractions from this LMWH were analyzed. The results showed that all the fractions had very similar disaccharide and 3-O-sulfo group-containing tetrasaccharide compositions, but the fraction containing larger-sized chains had higher antithrombin III-binding affinity.
Topics: Anticoagulants; Antithrombin III; Binding Sites; Disaccharides; Enoxaparin; Heparin, Low-Molecular-Weight; Humans; Molecular Weight; Oligosaccharides
PubMed: 29339133
DOI: 10.1016/j.xphs.2018.01.008 -
Organic & Biomolecular Chemistry May 2021Natural sulfated glycans are key players in inflammation through TLR4 activation; therefore synthetic exogenous sulfated saccharides can be used to downregulate...
Natural sulfated glycans are key players in inflammation through TLR4 activation; therefore synthetic exogenous sulfated saccharides can be used to downregulate inflammation processes. We have designed and synthesized new sulfated compounds based on small and biocompatible carbohydrates that are able to cross the BBB. A suitable protected donor and acceptor, obtained from a unique precursor, have been stereoselectively glycosylated to give an orthogonally protected cellobiose disaccharide. Selective deprotection and sulfation allowed the syntheses of four differentially sulfated disaccharides, which have been characterized by NMR, HRMS and MS/MS. Together with their partially protected precursors, the new compounds were tested on HEK-TLR4 cells. Our results show the potential of small oligosaccharides to modulate TLR4 activity, confirming the need for sulfation and the key role of the 6-sulfate groups to trigger TLR4 signalization.
Topics: Disaccharides
PubMed: 33908564
DOI: 10.1039/d1ob00692d