| 1. |
- Abrahamsson, Carl-Olof, et al.
(författare)
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Xylosylated naphthoic acid-amino acid conjugates for investigation of glycosaminoglycan priming.
- 2008
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Ingår i: Carbohydrate Research. - : Elsevier BV. - 1873-426X .- 0008-6215. ; 343:9, s. 1473-1477
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Tidskriftsartikel (refereegranskat)abstract
- Three different series of xylosylated naphthoic acid-amino acid conjugates containing one or two amino acid residues were synthesized for the investigation of glycosaminoglycan priming and potential use as anti-tumor drugs. All xylosylated naphthoic acid-conjugates inhibited the growth of normal lung fibroblasts to some extent, whereas the growth of tumor derived T24 carcinoma cells was not affected. There was no correlation between amino acid conjugation, retention time and the antiproliferative activity. Only one compound initiated the priming of glycosaminoglycans. Modification of the naphthalene ring with one or two amino acid residues did not have any effect on proteoglycan biosynthesis or glycosaminoglycan priming in T24 carcinoma cells.
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| 2. |
- Alexandersson, Elin, et al.
(författare)
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Complete H-1 and C-13 NMR spectral assignment of D-glucofuranose
- 2022
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Ingår i: Carbohydrate Research. - : Elsevier BV. - 0008-6215 .- 1873-426X. ; 511
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Tidskriftsartikel (refereegranskat)abstract
- Although D-glucose is the most common sugar in nature, only a few NMR studies have focused on its minor furanose forms, and they have been limited to the anomeric position. Here, complete H-1 and C-13 NMR spectral analysis of alpha- and beta-D-glucofuranose was performed, including signal assignment, chemical shifts, and coupling constants. Selective and non-selective 1D and 2D NMR experiments were used for the analysis, complemented by spin simulations and iterative spectral analysis.
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| 3. |
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| 4. |
- Amer, Adel, et al.
(författare)
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A regio- and stereo-controlled approach to triazoloquinoxalinyl C-nucleosides
- 2010
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Ingår i: Carbohydrate Research. - : Elsevier BV. - 0008-6215 .- 1873-426X. ; 345:17, s. 2474-2484
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Tidskriftsartikel (refereegranskat)abstract
- The synthesis of a new series of acyclic triazoloquinoxalinyl C-nucleosides and their transformation to their cyclic analogs are described following protection, activation, and deprotection with subsequent intramolecular nucleophilic substitution protocol. The antibacterial potency of the new compounds was determined using an inhibition zone diameter test. The results show that 3a and 2b exhibit good activity against Escherichia coli and Candida albicans. On the other hand, the cyclic mesylated C-nucleoside 13 showed activity against the Gram-positive bacteria (Staphylococcus aureus) and antifungal activity against C. albicans.
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| 5. |
- Andersson, Rolf, et al.
(författare)
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Structural studies of the lipopolysaccharide of Moritella viscosa strain M2-226
- 2012
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Ingår i: Carbohydrate Research. - : Elsevier BV. - 0008-6215 .- 1873-426X. ; 347, s. 164-167
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Tidskriftsartikel (refereegranskat)abstract
- The structure of the O-specific side chain of the lipopolysaccharide from the Gram-negative psychrophilic bacterium Moritella viscosa strain M2-226, responsible for the winter ulcer in Atlantic salmon, has been determined. Monosaccharide analysis and H-1 and C-13 NMR spectroscopy were employed to elucidate the structure. It was concluded that the polysaccharide is composed of a trisaccharide repeating unit with the following structure:)-> 3-beta-D-GlcpNAc-(1 -> 4)-[alpha-D-GlcpA-(1 -> 3)]-alpha-L-Fucp-(1 -> (C) 2011 Elsevier Ltd. All rights reserved.
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| 6. |
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| 7. |
- Araújo, Ana Catarina, et al.
(författare)
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A general route to xyloglucan-peptide conjugates for the activation of cellulose surfaces
- 2012
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Ingår i: Carbohydrate Research. - : Elsevier BV. - 0008-6215 .- 1873-426X. ; 354, s. 116-120
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Tidskriftsartikel (refereegranskat)abstract
- Cellulose is an attractive supporting matrix for diverse biotechnological applications, including chromatography, diagnostics, and tissue replacement/scaffolding, due to its renewable resource status, low cost, and low non-specific interaction with biomolecules. In an effort to expand the biofunctionality of cellulose materials, we present here a versatile method for the synthesis of xyloglucan-peptide conjugates that harness the strong xyloglucan-cellulose binding interaction for gentle surface modification. Xylogluco-oligosaccharide aminoalditols (XGO-NH2) were coupled to both linear and cyclic peptides, which contained the endothelial cell epitope Arg-Gly-Asp, in a facile two-step approach employing diethyl squarate cross-linking. Subsequent xyloglucan endo-transglycosylase-mediated coupling of the resulting XGO-GRGDS (Gly-Arg-Gly-Asp-Ser) and XGO-c[RGDfK]-PEG-PEG (cyclo[Arg-Gly-Asp-(D-Phe)-Lys]-PEG-PEG; where PEG is 8-amino-3,6-dioxaoctanoic acid) conjugates into high molecular mass xyloglucan yielded xyloglucan-RGD peptide conjugates suitable for cellulose surface activation. Notably, use of XGO-squaramate as a readily accessible, versatile intermediate overcomes previous limitations of solid-phase synthetic approaches to XGO-peptide conjugates, and furthermore allows the method to be generalized to a wide variety of polypeptides and proteins, as well as diverse primary amino compounds.
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| 8. |
- Arewang, Carl Johan, et al.
(författare)
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Synthesis of urine drug metabolites : glucuronic acid glycosides of phenol intermediates
- 2007
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Ingår i: Carbohydrate Research. - : Elsevier BV. - 0008-6215 .- 1873-426X. ; 342:7, s. 970-974
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Tidskriftsartikel (refereegranskat)abstract
- The investigation of drug metabolism requires substantial amount of metabolites. Isolation from urine is tedious, therefore, the material obtained by synthesis is preferred. Substantial amounts of three tentative drug metabolites, phenolic glucuronides, have been prepared using easily available glycosyl donors. The final products [3(2-N-methyl-N-isopropylaminoethoxy)phenyl] beta-D-glucopyranosiduronic acid, 4-amino-3,5-dimethylphenyl beta-D-glucopyranosiduronic acid and [2(S)-propanoyl-6-O-naphthyl] beta-D-glucopyranuronic acid are useful as, for example, reference material in metabolite investigations.
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| 9. |
- Avetyan, David L., et al.
(författare)
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Scalable total synthesis of natural vanillin-derived glucoside omega-esters
- 2022
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Ingår i: Carbohydrate Research. - : Elsevier BV. - 0008-6215 .- 1873-426X. ; 522, s. 108683-
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Tidskriftsartikel (refereegranskat)abstract
- The first total synthesis of vanilloloside, calleryanin, and a series of naturally occurring omega-esters of vanilloloside was realized through direct glycosylation of vanillin-based aglycones or late-stage derivatization of vanilloloside. All aglycones and their fragments were synthesized from vanillin as the sole aromatic precursor. Subsequently, these intermediates were used to construct various vanillin-derived glucoside omega-esters using a mild acidic deacetylation as the key synthetic step, providing the final products in the total yields of 10-50% and general purity of >95%. Additionally, the first operationally simple and sustainable synthesis of litseafoloside B was realized on large scale, avoiding the use of toxic solvents and reagents, providing an attractive alternative to isolation of this and other similar compounds from plant sources.
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| 10. |
- Bauer, S H J, et al.
(författare)
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A rapid and sensitive procedure for determination of 5-N-acetyl neuraminic acid in lipopolysaccharides of Haemophilus influenzae : a survey of 24 non-typeable H-influenzae strains
- 2001
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Ingår i: Carbohydrate Research. - 0008-6215 .- 1873-426X. ; 335:4, s. 251-260
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Tidskriftsartikel (refereegranskat)abstract
- In view of the importance of 5-N-acetyl neuraminic acid in bacterial pathogenesis, a sensitive, reproducible and reliable method for the determination of 5-N-acetyl neuraminic acid levels in lipopolysaccharide (LPS) is described and applied to 24 different non-typeable Haemophilus influenzae (NTHi) strains. The method involves analysis by high-performance anion-exchange chromatography with pulsed amperometric detection (HPAEC-PAD) of terminal 5-N-acetyl neuraminic acid residues released by neuraminidase treatment of O-deacylated LPS. The procedure is relatively fast and the instrumental effort is moderate. The results of the procedure were compared with data obtained by H-1 NMR and electrospray ionisation-mass spectrometry (ESI-MS). The analysis of LPS from 24 NTHi strains showed that 5-N-acetyl neuraminic acid was found to be a common constituent of LPS in NTHi. Only one strain (NTHi 432) did not show any sialylation. Molar ratios (LPS /5-N-acetyl neuraminic acid) ranged between 5/1 and 500/1. Several strains in which no 5-N-acetyl neuraminic acid could be determined by other methods including 1H NMR and ESI-MS were shown to contain 5-N-acetyl neuraminic acid by this HPAEC-PAD procedure. The method was applied to determine levels of terminal 5-N-acetyl neuraminic acid in LPS from NTHi strains grown under different conditions and mutant strains containing inactive LPS biosynthetic genes.
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