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Analytical Chemistry Aug 2021Heparan sulfates (HSs) are widely expressed glycans in the animal kingdom. HS plays a role in regulating cell differentiation/proliferation, embryonic development, blood...
Heparan sulfates (HSs) are widely expressed glycans in the animal kingdom. HS plays a role in regulating cell differentiation/proliferation, embryonic development, blood coagulation, inflammatory response, and viral infection. The amount of HS and its structural information are critically important for investigating the functions of HS in vivo. A sensitive and reliable quantitative technique for the analysis of HS from biological samples is under development. Here, we report a new labeling reagent for HS disaccharides analysis, 6-amino--(2-diethylamino)ethyl quinoline-2-carboamide (AMQC). The AMQC-conjugated disaccharides are analyzed by LC-MS/MS in positive mode, significantly improving the sensitivity. The use of AMQC coupled with authentic C-labeled HS disaccharide internal standards empowered us to determine the amount and the disaccharide composition of the HS on a single histological slide. We used this method to profile the levels of HS in the plasma/serum and tissues/organs to assist the disease prognosis in two animal models, including the acetaminophen (APAP)-induced acute liver injury mouse model and the burn injury mouse model. The method may uncover the roles of HS contributing to the diseases as well as provide a potential new set of biomarkers for disease diagnosis and prognosis.
Topics: Animals; Biomarkers; Chromatography, Liquid; Disaccharides; Heparitin Sulfate; Mice; Tandem Mass Spectrometry
PubMed: 34355888
DOI: 10.1021/acs.analchem.1c01761 -
Alimentary Pharmacology & Therapeutics Sep 2019
Topics: Disaccharides; Ferric Compounds; Humans; Hypophosphatemia; Incidence; Inflammatory Bowel Diseases; Iron; Maltose
PubMed: 31414537
DOI: 10.1111/apt.15443 -
Poultry Science Oct 2022This study was conducted to investigate the effects of in ovo injection of methionine (Met) and/or disaccharide (DS) on post-hatching pectoral muscle and small intestine...
Effects of methionine and/or disaccharide injected in the amnion of geese on post-hatching pectoral muscle and small intestine development, glycogen reserves, jejunum morphology, and digestive enzymes activities.
This study was conducted to investigate the effects of in ovo injection of methionine (Met) and/or disaccharide (DS) on post-hatching pectoral muscle and small intestine development, glycogen reserves, jejunum morphology, and jejunum digestive enzymes activities. A total of 600 fertilized eggs containing live embryo from geese were randomly assigned into 4 groups with 6 replicates and 25 eggs per replicate in a completely randomized design employing a 2 × 2 factorial experiment. Factors in 4 groups included noninjection, Met injection (5 g/L Met + 7.5 g/L NaCl), DS injection (25 g/L maltose + 25 g/L sucrose + 7.5 g/L NaCl), or DS plus Met injection (25 g/L maltose + 25 g/L sucrose + 5 g/L Met + 7.5g/L NaCl), respectively. In ovo nutritional injections were performed at day 23 of incubation, and the experiment until d 21 post-hatching. We found that in ovo feeding of Met increased relative weight of pectoral muscle and small intestine, jejunum alkaline phosphatase activities, and jejunum villus height and surface area. DS injection improved the relative weight of pectoral muscle, pectoral and liver glycogen contents, jejunum villus height, width, and surface area, and jejunum sucrase, Na/KATPase, and alkaline phosphatase activities. In addition, Met plus DS injection synergistically improved jejunum villus height and surface area. Therefore, Met plus DS injection is a suitable strategy for improving intestinal parameters in gosling during post-hatching periods.
Topics: Adenosine Triphosphatases; Alkaline Phosphatase; Amnion; Animals; Chickens; Disaccharides; Geese; Glycogen; Intestine, Small; Jejunum; Liver Glycogen; Maltose; Methionine; Ovum; Pectoralis Muscles; Racemethionine; Sodium Chloride; Sucrase; Sucrose
PubMed: 35986947
DOI: 10.1016/j.psj.2022.101867 -
Carbohydrate Polymers Nov 2022Non-sulfated forms of glycosaminoglycans (NSGAGs) including hyaluronan, chondroitin and heparosan with high-molecular-weight (HMW) are extensively used biomaterials,...
Non-sulfated forms of glycosaminoglycans (NSGAGs) including hyaluronan, chondroitin and heparosan with high-molecular-weight (HMW) are extensively used biomaterials, while NSGAGs oligosaccharides display strong bioactivities. However, microbial production of HMW-NSGAGs and oligosaccharides with specific size are always challenging. Here, a membrane shield strategy was developed to produce HMW-NSGAGs by recruiting type II NSGAG synthases in Corynebacterium glutamicum. By enhancing precursor supplies and reinforcing cell membrane, the MWs of hyaluronan, heparosan and chondroitin reached 4100 kDa, 3000 kDa and 2400 kDa, respectively. In parallel, a synchronized depolymerization-polymerization strategy was developed by co-expressing NSGAGs synthases and lyases. With cell membrane as a filter, we achieved the direct biosynthesis of NSGAGs tetrasaccharides and disaccharides. The titers of chondroitin, hyaluronan and heparosan tetrasaccharides and disaccharides reached 10.9 g L, 12.1 g L and 5.8 g L, respectively. The strategies developed here should also be applicable to the biosynthesis of other polysaccharides.
Topics: Chondroitin; Chondroitin Sulfates; Disaccharides; Glycosaminoglycans; Hyaluronic Acid; Oligosaccharides
PubMed: 35989030
DOI: 10.1016/j.carbpol.2022.119829 -
Biomacromolecules Mar 2021Glycosaminoglycans (GAGs) are conserved polysaccharides composed of linear repeating disaccharides and play crucial roles in multiple biological processes in animal...
Glycosaminoglycans (GAGs) are conserved polysaccharides composed of linear repeating disaccharides and play crucial roles in multiple biological processes in animal kingdom. However, saccharide-branched GAGs are rarely found, except the fucose-branched one from sea cucumbers. There was conjecture about the presence of disaccharide-branched GAG since 30 years ago, though not yet confirmed. Here, we report a GAG containing galactose-fucose branches from . This unique branch was confirmed as d-Gal-α1,2-l-Fuc by structural elucidation of oligosaccharides prepared from GAG. Bioassays indicated that oligomers with a larger degree of polymerization exhibited a potent anticoagulation by targeting the intrinsic tenase. Heptasaccharide was proven as the minimum fragment retaining the anticoagulant potential and showed 92.6% inhibition of venous thrombosis in vivo at sc. of 8 mg/kg with no obvious bleeding risks. These results not only solve a long-standing question about the presence of disaccharide-branched GAG in Holothuroidea, but open up new opportunities to develop safer anticoagulants.
Topics: Animals; Anticoagulants; Blood Coagulation; Disaccharides; Glycosaminoglycans; Sea Cucumbers
PubMed: 33616386
DOI: 10.1021/acs.biomac.0c01739 -
Chembiochem : a European Journal of... Mar 2024Carbohydrates are common co-solutes for the stabilization of proteins. The effect of carbohydrate solutions on the stability of collagen, the most abundant protein in...
Carbohydrates are common co-solutes for the stabilization of proteins. The effect of carbohydrate solutions on the stability of collagen, the most abundant protein in mammals, is, however, underexplored. In this work, we studied the thermal stability of collagen triple helices derived from a molecularly defined collagen model peptide (CMP), Ac-(Pro-Hyp-Gly) -NH , in solutions of six common mono- and disaccharides. We show that the carbohydrates stabilize the collagen triple helix in a concentration-dependent manner, with an increase of the melting temperature of up to 17 °C. In addition, we show that the stabilizing effect is similar for all studied sugars, including trehalose, which is otherwise considered a privileged bioprotectant. The results provided insight into the effects of sugar co-solutes on collagen triple helices and can aid the selection of storage environments for collagen-based materials and probes.
Topics: Animals; Collagen; Disaccharides; Temperature; Trehalose; Mammals
PubMed: 38233350
DOI: 10.1002/cbic.202300860 -
Journal of Economic Entomology Apr 2023Glucose aversion in the German cockroach, Blattella germanica (L.), results in behavioral resistance to insecticidal baits. Glucose-averse (GA) cockroaches reject foods...
Glucose aversion in the German cockroach, Blattella germanica (L.), results in behavioral resistance to insecticidal baits. Glucose-averse (GA) cockroaches reject foods containing glucose, even in relatively low concentrations, which protects the cockroaches from ingesting lethal amounts of toxic baits. Horizontal transfer of baits and the resulting secondary mortality have been documented in German cockroaches, including in insecticide resistant strains. However, the effects of the GA trait on secondary mortality have not been investigated. We hypothesized that ingestion of insecticide baits that contain glucose or glucose-containing disaccharides would result in behaviorally relevant glucose levels in the feces, possibly deterring coprophagy by GA nymphs. We fed adult female cockroaches hydramethylnon baits rich in either glucose, fructose, sucrose, or maltose and compared secondary mortality of GA and wild-type (WT) nymphs via coprophagy. When adult females were fed baits containing glucose, sucrose, or maltose and their feces offered to nymphs, secondary mortality was significantly lower in GA nymphs than in WT nymphs. However, survival of GA and WT nymphs was similar on feces generated by adult females fed fructose bait. Analysis of feces indicated that disaccharides in baits were hydrolyzed into glucose, some of which was excreted in the feces of females that ingested the bait. Based on these results, we caution that baits containing glucose or glucose-containing oligosaccharides may impede cockroach interventions; while GA adults and large nymphs avoid ingesting such baits, first instars reject the glucose-containing feces of any WT cockroaches that consumed the bait.
Topics: Female; Animals; Blattellidae; Glucose; Disaccharides; Maltose; Insecticides; Cockroaches; Sucrose; Nymph; Fructose
PubMed: 36888567
DOI: 10.1093/jee/toad030 -
Biotechnology Advances Nov 2022Lactulose, a semisynthetic nondigestive disaccharide with versatile applications in the food and pharmaceutical industries, has received increasing interest due to its... (Review)
Review
Lactulose, a semisynthetic nondigestive disaccharide with versatile applications in the food and pharmaceutical industries, has received increasing interest due to its significant health-promoting effects. Currently, industrial lactulose production is exclusively carried out by chemical isomerization of lactose via the Lobry de Bruyn-Alberda van Ekenstein (LA) rearrangement, and much work has been directed toward improving the conversion efficiency in terms of lactulose yield and purity by using new chemo-catalysts and integrated catalytic-purification systems. Lactulose can also be produced by an enzymatic route offering a potentially greener alternative to chemo-catalysis with fewer side products. Compared to the controlled trans-galactosylation by β-galactosidase, directed isomerization of lactose with high isomerization efficiency catalyzed by the most efficient lactulose-producing enzyme, cellobiose 2-epimerase (CE), has gained much attention in recent decades. To further facilitate the industrial translation of CE-based lactulose biotransformation, numerous studies have been reported on improving biocatalytic performance through enzyme mediated molecular modification. This review summarizes recent developments in the chemical and enzymatic production of lactulose. Related catalytic mechanisms are also highlighted and described in detail. Emerging techniques that aimed at advancing lactulose production, such as the boronate affinity-based technique and molecular biological techniques, are reviewed. Finally, perspectives on challenges and opportunities in lactulose production and purification are also discussed.
Topics: Catalysis; Cellobiose; Isomerism; Lactose; Lactulose; Racemases and Epimerases; beta-Galactosidase
PubMed: 35901861
DOI: 10.1016/j.biotechadv.2022.108021 -
Bioconjugate Chemistry Jun 2022Antibody-drug conjugates (ADCs) hold great promise for targeted cancer cell killing. Site-specific antibody-drug conjugation is highly desirable for synthesizing...
Antibody-drug conjugates (ADCs) hold great promise for targeted cancer cell killing. Site-specific antibody-drug conjugation is highly desirable for synthesizing homogeneous ADCs with optimal safety profiles and high efficacy. We have recently reported that azide-functionalized disaccharide oxazolines of the Man1,4GlcNAc core were an efficient substrate of wild-type endoglycosidase Endo-S2 for Fc glycan remodeling and conjugation. In this paper, we report the synthesis and evaluation of new disaccharide oxazolines as enzyme substrates for examining the scope of the site-specific conjugation. Thus, azide-functionalized disaccharide oxazolines derived from Man1,4GlcNAc, Glc1,4GlcNAc, and Gal1,4GlcNAc (LacNAc) were synthesized. Enzymatic evaluation revealed that wild-type Endo-S2 demonstrated highly relaxed substrate specificity and could accommodate all the three types of disaccharide derivatives for transglycosylation to provide site-specific azide-tagged antibodies, which were readily clicked with a payload to generate homogeneous ADCs. Moreover, we also found that Endo-S2 was able to accommodate drug-preloaded minimal disaccharide oxazolines as donor substrates for efficient glycan transfer, enabling a single-step and site-specific antibody-drug conjugation without the need of an antibody click reaction. The ability of Endo-S2 to accommodate simpler and more easily synthesized disaccharide oxazoline derivatives for Fc glycan remodeling further expanded the scope of this bioconjugation method for constructing homogeneous antibody-drug conjugates in a single-step manner. Finally, cell-based assays indicated that the synthetic homogeneous ADCs demonstrated potent targeted cancer cell killing.
Topics: Antibodies; Azides; Disaccharides; Immunoconjugates; Immunoglobulin Fc Fragments; Polysaccharides
PubMed: 35543724
DOI: 10.1021/acs.bioconjchem.2c00142 -
Jornal de Pediatria 2019This narrative review aimed to provide practitioners a synthesis of the current knowledge on the role of a low Fermentable Oligosaccharides Disaccharides Monosaccharides... (Review)
Review
OBJECTIVE
This narrative review aimed to provide practitioners a synthesis of the current knowledge on the role of a low Fermentable Oligosaccharides Disaccharides Monosaccharides and Polyols diet in reducing symptoms associated with functional abdominal pain disorders in children. This review is focused on the pathophysiology, efficacy and criticism of low Fermentable Oligosaccharides Disaccharides Monosaccharides and Polyols diet in children.
SOURCES
Cochrane Database, Pubmed and Embase were searched using specific terms for Fermentable Oligosaccharides Disaccharides Monosaccharides and Polyols diet interventions and functional abdominal pain disorders.
SUMMARY OF THE FINDINGS
In children, only one Randomized Control Trial and one open-label study reported positive results of low Fermentable Oligosaccharides Disaccharides Monosaccharides and Polyols diet; one Randomized Control Trial showed exacerbation of symptoms with fructans in children with Irritable Bowel Syndrome; no effect was found for the lactose-free diet whilst fructose-restricted diets were effective in 5/6 studies.
CONCLUSIONS
In children there are few trials evaluating low Fermentable Oligosaccharides Disaccharides Monosaccharides and Polyols in functional abdominal pain disorders, with encouraging data on the therapeutic efficacy particularly of fructose-restricted diet. Additional efforts are still needed to fill this research gap and clarify the most efficient way for tailoring dietary restrictions based on the patient's tolerance and/or identification of potential biomarkers of low Fermentable Oligosaccharides Disaccharides Monosaccharides and Polyols efficacy, to maintain nutritional adequacy and to simplify the adherence to diet by labeling Fermentable Oligosaccharides Disaccharides Monosaccharides and Polyols content in commercial products.
Topics: Abdominal Pain; Diet; Diet, Carbohydrate-Restricted; Disaccharides; Humans; Irritable Bowel Syndrome; Monosaccharides; Oligosaccharides
PubMed: 31028745
DOI: 10.1016/j.jped.2019.03.004