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Search for "amino sugars" in Full Text gives 9 result(s) in Beilstein Journal of Organic Chemistry.
A myo-inositol dehydrogenase involved in aminocyclitol biosynthesis of hygromycin A
Beilstein J. Org. Chem. 2024, 20, 589–596, doi:10.3762/bjoc.20.51
- noticed that some other enzymes from this PFAM are also paired with aminotransferases to generate amino sugars found in natural products [25][26], so we looked to see if aminotransferases are commonly found by PF01408 sequences. We observed three separate aminotransferase PFAMs near many of the PF01408
Synthesis of multiply fluorinated N-acetyl-D-glucosamine and D-galactosamine analogs via the corresponding deoxyfluorinated glucosazide and galactosazide phenyl thioglycosides
Beilstein J. Org. Chem. 2021, 17, 1086–1095, doi:10.3762/bjoc.17.85
- . Keywords: amino sugars; deoxyfluorination; fluorinated carbohydrates; hexosamine hemiacetals; thioglycosides; Introduction Fluorinated carbohydrates are versatile carbohydrate mimetics used to probe or manipulate the recognition of carbohydrates by carbohydrate-binding proteins or carbohydrate-processing
A stereoselective and flexible synthesis to access both enantiomers of N-acetylgalactosamine and peracetylated N-acetylidosamine
Beilstein J. Org. Chem. 2018, 14, 856–860, doi:10.3762/bjoc.14.71
- relationship studies. Several strategies for the synthesis of 2-amino sugars have been published so far. In one exemplary straightforward approach, GalNAc was prepared by inverting the stereogenic center at the C-4 position of N-acetylglucosamine (GlcNAc) [10]. However, the necessity of using a 2-amino sugar
- the missing isomers of 2-amino sugars, as well as new derivatives are still highly desired. The here presented flexible approach towards GalNAc and IdoNAc from epoxythreitol 5 is a first step to answer this request. These molecules can be approached from tartaric acid (3), which already provides two
- peracetylated to yield compounds 8a and 8b. The azide function was reduced with H2 and Pd/C in acetic anhydride to gain the fully acetylated amino sugars 2a and 2b. In the final step, the compounds were deprotected using a mixture of MeOH/H2O/Et3N to yield D-GalNAc (1a) and L-GalNAc (1b). As proof of concept
Aminosugar-based immunomodulator lipid A: synthetic approaches
Beilstein J. Org. Chem. 2018, 14, 25–53, doi:10.3762/bjoc.14.3
- chain β-hydroxy fatty acids, anomeric phosphorylation and the synthesis of binary glycosyl phosphodiesters involving two amino sugars. Explicit structure–activity relationships data obtained with synthetic lipid A derivatives would also help to design novel therapeutic approaches for sepsis and
Diosgenyl 2-amino-2-deoxy-β-D-galactopyranoside: synthesis, derivatives and antimicrobial activity
Beilstein J. Org. Chem. 2017, 13, 2310–2315, doi:10.3762/bjoc.13.227
- Supporting Information File 1 for experimental and NMR data). To obtain the N-alkyl derivatives of 4, a method called “two-step reductive alkylation of amines” was chosen. This method was successfully used to prepare N-alkyl derivatives of other amino sugars, including diosgenyl aminoglucosides [34][35]. The
Synthesis and in vitro cytotoxicity of acetylated 3-fluoro, 4-fluoro and 3,4-difluoro analogs of D-glucosamine and D-galactosamine
Beilstein J. Org. Chem. 2016, 12, 750–759, doi:10.3762/bjoc.12.75
- -2-azido-hexopyranoses have potential as synthons in oligosaccharide assembly. Keywords: amino sugars; cytotoxicity; fluorinated carbohydrates; fluorine; hexosamines; Introduction Derivatives of D-glucosamine (GlcN) and D-galactosamine (GalN) are essential amino sugar components of glycans in
- glycoproteins, glycolipids and proteoglycans. As such, they participate in functions performed by cell-surface glycans including cell adhesion and signaling [1]. Unnatural analogs of these amino sugars prepared by a selective replacement of a hydroxy group by fluorine have proved valuable tools to perturb
- glycan and glycosaminoglycan biosynthesis [2][3], to inhibit amino sugars processing enzymes [4][5], to probe interactions of amino sugars with their target enzymes and lectins [6][7], or to increase the hydrolytic stability of the glycosidic bond in amino sugar glycosides [8][9]. For example, acetylated
Electrochemical generation of 2,3-oxazolidinone glycosyl triflates as an intermediate for stereoselective glycosylation
Beilstein J. Org. Chem. 2012, 8, 456–460, doi:10.3762/bjoc.8.52
- amino sugars [7][8], the selectivity highly depends on the nature of the glycosyl acceptors and reaction conditions. In the last decade, 2,3-oxazolidinone protected 2-amino-2-deoxy-glycosides have been developed as glycosyl donors for the stereoselective synthesis of amino sugars [9][10][11][12][13][14
Amine-linked diglycosides: Synthesis facilitated by the enhanced reactivity of allylic electrophiles, and glycosidase inhibition assays
Beilstein J. Org. Chem. 2011, 7, 1115–1123, doi:10.3762/bjoc.7.128
- reaction was much less regioselective than the Mitsunobu couplings. Moreover, the major regioisomer in the palladium-catalysed reaction was the 2-amino sugar, whereas in the Mitsunobu reactions, the 4-amino sugars were formed exclusively. A small amount of stereochemical scrambling of an intermediate π
Addition of lithiated enol ethers to nitrones and subsequent Lewis acid induced cyclizations to enantiopure 3,6-dihydro-2H-pyrans – an approach to carbohydrate mimetics
Beilstein J. Org. Chem. 2010, 6, No. 75, doi:10.3762/bjoc.6.75
- ]. A final hydrogenation step gave aminopyran 30 in high overall yield. Aminopyrans 24, 26, 28 and 30 can be regarded as mimetics of differently configured (2-deoxy) 4-amino sugars [24][25][26]. Aminopyrans 24 and 28 have already been linked via amide bonds to the thiol shell of gold nanoparticles
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