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Applied Microbiology and Biotechnology May 2019Lactose is a natural disaccharide obtained from the milk of most mammals and a waste product of cheese and casein manufacturing. Over the past decades, lactose in whey... (Review)
Review
Lactose is a natural disaccharide obtained from the milk of most mammals and a waste product of cheese and casein manufacturing. Over the past decades, lactose in whey has increasingly been promoted as an important resource, and an increasing number of significant advances have been made to investigate its healthy and functional properties. Lactose can be biotransformed into many kinds of derivatives, including galacto-oligosaccharides, epilactose, lactulose, lactosucrose, and D-tagatose. Biological efficiency and safety are critical for the enzymatic production of lactose derivatives from lactose. These lactose derivatives show a range of prominent physiological features and effects, such as prebiotic properties, indigestibility, and obesity prevention, which can be utilized in the pharmaceutical, health, and food industries. In this review, we present the properties and physiological effects of lactose derivatives, detailing their biological production by various enzymes and their applications in dairy products, especially directly in the milk industry.
Topics: Animals; Disaccharides; Humans; Lactose; Oligosaccharides; Prebiotics; Whey
PubMed: 30911789
DOI: 10.1007/s00253-019-09755-6 -
Food Chemistry Feb 2021Mass spectrometry imaging (MSI) is a powerful technique for investigating the biomolecular locations within tissues. However, the isomeric compounds are rarely...
Mass spectrometry imaging (MSI) is a powerful technique for investigating the biomolecular locations within tissues. However, the isomeric compounds are rarely distinguished due to inability of MSI to differentiate isomers in the probing area. Coupling tandem mass spectrometry with MSI can facilitate differentiating isomeric compounds. Here MALDI-TOF/TOF tandem mass spectrometry imaging approach was applied to probing the spatial distributions of isomeric disaccharides in plant tissues. First, MS/MS imaging analysis of disaccharide-matrix droplet spots demonstrated the feasibility of distinguishing isomeric species in tissues, by measuring the relative intensity of specific fragments. Then, tandem MS imaging of disaccharides in onion bulb tissues indicated that sucrose and other unknown non-sucrose disaccharides exhibit heterogeneous locations throughout the tissues. This method enables us to image disaccharide isomers differentially in biological tissues, and to discover new saccharide species in plant. This work also emphasizes the necessity of considering isobaric compounds when interpreting MSI results.
Topics: Disaccharides; Isomerism; Onions; Plant Roots; Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization; Sucrose; Tandem Mass Spectrometry
PubMed: 33092001
DOI: 10.1016/j.foodchem.2020.127984 -
Immunology and Cell Biology Aug 2005Cancer-associated mucins show frequent alterations of their oligosaccharide chain profile, with a switch to unmask normally cryptic O-glycan backbone and core regions....
Cancer-associated mucins show frequent alterations of their oligosaccharide chain profile, with a switch to unmask normally cryptic O-glycan backbone and core regions. Epithelial tumour cells typically show overexpression of the uncovered Gal(beta)1-3GalNAc(alpha)-O-Ser/Thr (Core 1) structure, known as the T antigen or the Thomsen-Friedenreich antigen, the oligosaccharide chain of which is called the Thomsen-Friedenreich disaccharide (TFD). T antigen expression has been associated with immunosuppression, metastasis dissemination, and the proliferation of cancer cells. Several different strategies have been used to trigger a specific immune response to TFD. Natural T antigen and synthetic TFD residues have low immunodominance. In the T antigen, flexibility of the glycosidic bond reduces the immunogenicity of the sugar residue. Enhanced rigidity should favour certain glycan conformations and thereby improve TFD immunotargeting. We propose the term 'glycan engineering' for this approach. Such engineering of TFD should reduce the flexibility of its glycan moiety and thereby enhance its stability, rigidity and immunogenicity.
Topics: Animals; Antigens, Tumor-Associated, Carbohydrate; Carbohydrate Conformation; Disaccharides; Drug Design; Neoplasms; Polysaccharides
PubMed: 16033536
DOI: 10.1111/j.1440-1711.2005.01348.x -
Journal of the American Chemical Society Sep 2014The disaccharide galactose-β1,3-N-acetylgalactosamine (Galβ1,3-GalNAc) attached to serine and/or threonine residues of proteins, also known as the Thomsen-Friedenreich...
The disaccharide galactose-β1,3-N-acetylgalactosamine (Galβ1,3-GalNAc) attached to serine and/or threonine residues of proteins, also known as the Thomsen-Friedenreich (TF) antigen, is highly expressed in various types of human carcinomas. It has been shown to contribute to tumor development, progression, and metastasis. However, current methods have limited power in detecting and imaging TF antigens among a variety of complex cell-surface glycans. Here we describe a tandem enzymatic strategy to detect and label TF antigen disaccharide with high sensitivity and selectivity. We demonstrate that this strategy enables detection of TF antigens on proteins, profiling and identification of unknown TF antigen-modified glycoproteins, and simultaneous labeling of multiple forms of complex glycan motifs on the same cell. This approach expands the capability of glycan labeling to probe the functional role of TF antigens in cancer biology.
Topics: Antigens, Tumor-Associated, Carbohydrate; Diagnostic Imaging; Disaccharides; Horseradish Peroxidase; Humans; Jurkat Cells; MCF-7 Cells; Molecular Structure; Neoplasms
PubMed: 25157422
DOI: 10.1021/ja5054225 -
Carbohydrate Research Apr 2017A disaccharide repeating unit of the O-antigen from Burkholderia ambifaria, 6-deoxy-β-d-Alt-(1 → 4)-α-d-Rha-O(CH)NH (1), and its dimer and trimer,...
A disaccharide repeating unit of the O-antigen from Burkholderia ambifaria, 6-deoxy-β-d-Alt-(1 → 4)-α-d-Rha-O(CH)NH (1), and its dimer and trimer, 6-deoxy-β-d-Alt-(1 → 4)-α-d-Rha-(1 → 3)-6-deoxy-β-d-Alt-(1 → 4)-α-d-Rha-O(CH)NH (2) and 6-deoxy-β-d-Alt-(1 → 4)-α-d-Rha-(1 → 3)-6-deoxy-β-d-Alt-(1 → 4)-α-d-Rha-(1 → 3)-6-deoxy-β-d-Alt-(1 → 4)-α-d-Rha-O(CH)NH (3), were synthesized via a convergent strategy. The key disaccharyl thioglycoside 4 as a glycosyl donor was stereoselectively assembled by glycosylation of rhammnosyl acceptor 5 with 6-deoxy-altrosyl trichloroacetimidate donor 6b. The glycosidation of 4 with 3-azidopropanol followed by global deprotection afforded the target disaccharide 1. Further elongation of the carbohydrate chain of this glycosidation product with the disaccharyl donor 4 followed by global deprotection generated rapidly the dimeric tetrasaccharide 2 and the trimeric hexasaccharide 3 in a convergent [2 + 2] and [2 + 2 + 2] manner, respectively.
Topics: Burkholderia; Carbohydrate Conformation; Carbohydrate Sequence; Disaccharides; O Antigens
PubMed: 28288346
DOI: 10.1016/j.carres.2017.03.004 -
Carbohydrate Polymers Jan 2013Force spectroscopy has been used to investigate the interaction between the disaccharide β-galactobiose and the pro-metastatic regulatory protein galectin-3 (Gal3). The...
Force spectroscopy has been used to investigate the interaction between the disaccharide β-galactobiose and the pro-metastatic regulatory protein galectin-3 (Gal3). The studies revealed specific interactions characterised by an off-rate dissociation constant k(off)=0.33 s(-1) and interaction distance x=0.2 nm at zero applied force. These data suggest a lifetime for the interaction of 3.0 s. The results are consistent with the hypothesis that oral consumption of modified citrus pectin controls cancer metastasis by inhibiting the role of Gal3. The modification is considered to facilitate binding of pectin-derived galactan sidechains to Gal3 and inhibition of the roles of Gal3 as a pro-metastatic regulatory protein.
Topics: Disaccharides; Galactans; Galectin 3; Humans; Microscopy, Atomic Force; Neoplasms; Pectins; Recombinant Proteins
PubMed: 23218331
DOI: 10.1016/j.carbpol.2012.08.104 -
Analytical and Bioanalytical Chemistry Jul 2019This review summarizes progress in analysis of glycosaminoglycans using mass spectrometry (MS) approaches. The specific areas covered include analytical challenges,... (Review)
Review
This review summarizes progress in analysis of glycosaminoglycans using mass spectrometry (MS) approaches. The specific areas covered include analytical challenges, disaccharide analysis, top-down and bottom-up techniques, sequence analysis, and future perspectives. A brief outline of the complexity and heterogeneity of these unique saccharides and their analysis is provided along with examples of several recent studies. Unique problems and challenges in the characterization of glycosaminoglycans are discussed along with many of the analytical tools used in particular MS methods and the types of information provided. Advances in MS-related technologies have provided more sensitive and accurate detection and sequence analysis of this complex and chemically unique class of bioconjugates. Effective MS-based methods and automated data handling with bioinformatics tools have been developed for disaccharide analysis, top-down and bottom-up analysis, and sequencing studies of relatively short oligosaccharides. It is envisioned that further improvements in MS technologies along with bioinformatics methods will make sequencing studies of longer glycosaminoglycan chains easier and faster.
Topics: Carbohydrate Sequence; Computational Biology; Disaccharides; Glycosaminoglycans; Mass Spectrometry
PubMed: 30911798
DOI: 10.1007/s00216-019-01722-4 -
Rapid Communications in Mass... Dec 2013Carbohydrates are highly variable in structure owing to differences in their anomeric configurations, monomer stereochemistry, inter-residue linkage positions and...
RATIONALE
Carbohydrates are highly variable in structure owing to differences in their anomeric configurations, monomer stereochemistry, inter-residue linkage positions and general branching features. The separation of carbohydrate isomers poses a great challenge for current analytical techniques.
METHODS
The isomeric heterogeneity of disaccharide ions and monosaccharide-glycolaldehyde product ions was evaluated using electrospray traveling wave ion mobility mass spectrometry (Synapt G2 high-definition mass spectrometer) in both positive and negative ion modes.
RESULTS
The separation of isomeric disaccharide ions was observed but not fully achieved based on their mobility profiles. The mobilities of isomeric product ions, the monosaccharide-glycolaldehydes, derived from different disaccharide isomers were measured. Multiple mobility peaks were observed for both monosaccharide-glycolaldehyde cations and anions, indicating that there was more than one structural configuration in the gas phase as verified by NMR in solution. More importantly, the mobility patterns for isomeric monosaccharide-glycolaldehyde product ions were different, which enabled partial characterization of their respective disaccharide ions. Abundant disaccharide cluster ions were also observed. The results showed that a majority of isomeric cluster ions had different drift times and, moreover, more than one mobility peak was detected for a number of specific cluster ions.
CONCLUSIONS
It is demonstrated that ion mobility mass spectrometry is an advantageous method to assess the isomeric heterogeneity of carbohydrate compounds. It is capable of differentiating different types of carbohydrate ions having identical m/z values as well as multiple structural configurations of single compounds.
Topics: Disaccharides; Isomerism; Mass Spectrometry
PubMed: 24591031
DOI: 10.1002/rcm.6720 -
Journal of the American Chemical Society Apr 2009Designing better small-molecule discovery libraries requires having methods to assess the consequences of different synthesis decisions on the biological performance of...
Designing better small-molecule discovery libraries requires having methods to assess the consequences of different synthesis decisions on the biological performance of resulting library members. Since we are particularly interested in how stereochemistry affects performance in biological assays, we prepared a disaccharide library containing systematic stereochemical variations, assayed the library for different biological effects, and developed methods to assess the similarity of performance between members across multiple assays. These methods allow us to ask which subsets of stereochemical features best predict similarity in patterns of biological performance between individual members and which features produce the greatest variation of outcomes. We anticipate that the data-analysis approach presented here can be generalized to other sets of biological assays and other chemical descriptors. Methods to assess which structural features of library members produce the greatest similarity in performance for a given set of biological assays should help prioritize synthesis decisions in second-generation library development targeting the underlying cell-biological processes. Methods to assess which structural features of library members produce the greatest variation in performance should help guide decisions about what synthetic methods need to be developed to make optimal small-molecule screening collections.
Topics: Adipocytes; Animals; Cell Differentiation; Cells, Cultured; Combinatorial Chemistry Techniques; Disaccharides; Glycosylation; Mice; Mice, Knockout; Molecular Structure; Small Molecule Libraries; Stereoisomerism; Structure-Activity Relationship
PubMed: 19298063
DOI: 10.1021/ja806583y -
Carbohydrate Research Mar 2014The stereoselective preparation of the β-d-GlcNAc-(1→4)-D-Glc disaccharide starting from known...
The stereoselective preparation of the β-d-GlcNAc-(1→4)-D-Glc disaccharide starting from known 4-O-[6-O-(1-methoxy-1-methylethyl)-3,4-O-isopropylidene-β-d-talopyranosyl]-2,3:5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal (2), in turn easily obtained from lactose, is reported. Key steps of this new procedure, that avoids the glycosylation reaction, are (a) a first epimerization at C-4' through an unusual procedure involving a completely stereospecific hydroboration-oxidation of the enol ether group of the hex-4-enopyranoside 4, obtained from 3 by base promoted acetone elimination, (b) an amination with inversion by S(N)2 reaction on an imidazylate intermediate, and, finally, (c) N-acetylation followed by complete deprotection.
Topics: Acetylation; Acetylglucosamine; Carbohydrate Sequence; Disaccharides; Glycosides; Glycosylation; Lactose; Molecular Sequence Data; Stereoisomerism
PubMed: 24614689
DOI: 10.1016/j.carres.2014.01.020