123212-53-3Relevant articles and documents
Regioselective Glycosylation Strategies for the Synthesis of Group Ia and Ib Streptococcus Related Glycans Enable Elucidating Unique Conformations of the Capsular Polysaccharides
Del Bino, Linda,Calloni, Ilaria,Oldrini, Davide,Raso, Maria Michelina,Cuffaro, Rossella,Ardá, Ana,Codée, Jeroen D. C.,Jiménez-Barbero, Jesús,Adamo, Roberto
supporting information, p. 16277 - 16287 (2019/11/14)
Group B Streptococcus serotypes Ia and Ib capsular polysaccharides are key targets for vaccine development. In spite of their immunospecifity these polysaccharides share high structural similarity. Both are composed of the same monosaccharide residues and
NOVEL INTERMEDIATES FOR THE PREPARATION OF GBS POLYSACCHARIDE ANTIGENS
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Paragraph 0084, (2019/01/30)
The present invention generally refers to novel intermediate polysaccharide units, useful for the preparation of polysaccharide antigen of GBS Ia, Ib and III; the invention also refers to a process for their preparation and their use as intermediate for t
Ionic-liquid supported rapid synthesis of an: N -glycan core pentasaccharide on a 10 g scale
Li, Wei,Gao, Yu,Li, Qing,Li, Zhong-Jun
supporting information, p. 4720 - 4727 (2018/07/06)
A new and efficient Ionic Liquid-Supported Oligosaccharide Synthesis (ILSOS) strategy for an N-linked core pentasaccharide on a 10 g scale is reported. This new ILSOS includes a new spacer for an IL support, a new tagging strategy, and fast, efficient and orthogonal removal of the ionic-liquid support, producing the N-linked core pentasaccharide with direct applicability potential in a short time, with high yield and on a large gram scale.
'Naked' and hydrated conformers of the conserved core pentasaccharide of N-linked glycoproteins and its building blocks
Barry, Conor S.,Cocinero, Emilio J.,Carcabal, Pierre,Gamblin, David P.,Stanca-Kaposta, E. Cristina,Remmert, Sarah M.,Fernandez-Alonso, Maria C.,Rudic, Svemir,Simons, John P.,Davis, Benjamin G.
supporting information, p. 16895 - 16903 (2013/12/04)
N-glycosylation of eukaryotic proteins is widespread and vital to survival. The pentasaccharide unit -Man3GlcNAc2- lies at the protein-junction core of all oligosaccharides attached to asparagine side chains during this process. Although its absolute conservation implies an indispensable role, associated perhaps with its structure, its unbiased conformation and the potential modulating role of solvation are unknown; both have now been explored through a combination of synthesis, laser spectroscopy, and computation. The proximal -GlcNAc-GlcNAc- unit acts as a rigid rod, while the central, and unusual, -Man-β-1,4-GlcNAc- linkage is more flexible and is modulated by the distal Man-α-1,3- and Man-α-1,6- branching units. Solvation stiffens the 'rod' but leaves the distal residues flexible, through a β-Man pivot, ensuring anchored projection from the protein shell while allowing flexible interaction of the distal portion of N-glycosylation with bulk water and biomolecular assemblies.
Combining weak affinity chromatography, NMR spectroscopy and molecular simulations in carbohydrate-lysozyme interaction studies
Landstroem, Jens,Bergstroem, Maria,Hamark, Christoffer,Ohlson, Sten,Widmalm, Goeran
supporting information; experimental part, p. 3019 - 3032 (2012/05/07)
By examining the interactions between the protein hen egg-white lysozyme (HEWL) and commercially available and chemically synthesized carbohydrate ligands using a combination of weak affinity chromatography (WAC), NMR spectroscopy and molecular simulations, we report on new affinity data as well as a detailed binding model for the HEWL protein. The equilibrium dissociation constants of the ligands were obtained by WAC but also by NMR spectroscopy, which agreed well. The structures of two HEWL-disaccharide complexes in solution were deduced by NMR spectroscopy using 1H saturation transfer difference (STD) effects and transferred 1H,1H-NOESY experiments, relaxation-matrix calculations, molecular docking and molecular dynamics simulations. In solution the two disaccharides β-d-Galp-(1→4) -β-d-GlcpNAc-OMe and β-d-GlcpNAc-(1→4)-β-d-GlcpNAc-OMe bind to the B and C sites of HEWL in a syn-conformation at the glycosidic linkage between the two sugar residues. Intermolecular hydrogen bonding and CH/π-interactions form the basis of the protein-ligand complexes in a way characteristic of carbohydrate-protein interactions. Molecular dynamics simulations with explicit water molecules of both the apo-form of the protein and a ligand-protein complex showed structural change compared to a crystal structure of the protein. The flexibility of HEWL as indicated by a residue-based root-mean-square deviation analysis indicated similarities overall, with some residue specific differences, inter alia, for Arg61 that is situated prior to a flexible loop. The Arg61 flexibility was notably larger in the ligand-complexed form of HEWL. N,N′-Diacetylchitobiose has previously been observed to bind to HEWL at the B and C sites in water solution based on 1H NMR chemical shift changes in the protein whereas the disaccharide binds at either the B and C sites or the C and D sites in different crystal complexes. The present study thus highlights that protein-ligand complexes may vary notably between the solution and solid states, underscoring the importance of targeting the pertinent binding site(s) for inhibition of protein activity and the advantages of combining different techniques in a screening process. The Royal Society of Chemistry 2012.
Toward fully synthetic homogeneous β -human Follicle-Stimulating hormone (β -hFSH) with a biantennary N-linked dodecasaccharide. synthesis of β -hFSH with chitobiose units at the natural linkage sites
Nagorny, Pavel,Fasching, Bernhard,Li, Xuechen,Chen, Gong,Aussedat, Baptiste,Danishefsky, Samuel J.
supporting information; experimental part, p. 5792 - 5799 (2009/09/24)
A highly convergent synthesis of the sialic acid-rich biantennary N-linked glycan found in human glycoprotein hormones and its use in the synthesis of a fragment derived from the β -domain of human Follicle-Stimulating Hormone (hFSH) are described. The synthesis highlights the use of the Sinay radical glycosidation protocol for the simultaneous installation of both biantennary side-chains of the dodecasaccharide as well as the use of glycal chemistry to construct the tetrasaccharide core in an efficient manner. The synthetic glycan was used to prepare the glycosylated 20-27aa domain of the β -subunit of hFSH under a Lansbury aspartylation protocol. The proposed strategy for incorporating the prepared N-linked dodecasaccharide-containing 20-27aa domain into β -hFSH subunit was validated in the context of a model system, providing protected β -hFSH subunit functionalized with chitobiose at positions 7 and24.
Efficient routes to ethyl-2-deoxy-2-phthalimido-1-β-D-thio- galactosamine derivatives via epimerization of the corresponding glucosamine compounds
Hederos, Markus,Konradsson, Peter
, p. 297 - 320 (2007/10/03)
Short synthetic routes to protected ethyl 2-deoxy-2-phthalimido-1-β-D- thio-galactosamine derivatives via epimerization of the corresponding glucosamine compounds are described. Starting from D-glucosamine hydrochloride, the epimerizations were performed
Synthesis of neomycin analogs to investigate aminoglycoside-RNA interactions
Seeberger, Peter H.,Baumann, Michael,Zhang, Guangtao,Kanemitsu, Takuya,Swayze, Eric E.,Hofstadler, Steven A.,Griffey, Richard H.
, p. 1323 - 1326 (2007/10/03)
A series of novel aminoglycoside oligosaccharide analogs containing a 2,5-dideoxystreptamine core scaffold was prepared to study aminoglycoside binding to the small subunit of 16S rRNA. A set of monosaccharide building blocks carrying amino groups in diff
1,2-Diacetals in synthesis: Total synthesis of a glycosylphosphatidylinositol anchor of Trypanosoma brucei
Baeschlin, Daniel K.,Chaperon, Andre R.,Green, Luke G.,Hahn, Michael G.,Ince, Stuart J.,Ley, Steven V.
, p. 172 - 186 (2007/10/03)
A full account on a total synthesis of GPI anchor 1 employing butanediacetal (BDA) groups and a chiral bis(dihydropyran) is presented. The reactivity of selenium and thio glycosides was tuned by the use of BDA groups. This allowed the assembly of an appro
Synthesis of N-Acetylallosamine-Derived Disaccharides
Maloisel, Jean-Luc,Vasella, Andrea
, p. 1491 - 1514 (2007/10/02)
The protected disaccharide 44, a precursor for the synthesis of allosamidin, was prepared from the glycosyl acceptor 8 and the donors 26-28, best yields being obtained with the trichloroacetimidate 28 (Scheme 6).Glycosidation of 8 or of 32 by the triacetylated, less reactive donors 38-40 gave the disaccharides 46 and 45, respectively, in lower yields (Scheme 7).Regioselective glycosidation of the diol 35 by the donors 38-40 gave 42, the axial, intramolecularly H-bonded OH-C(3) group reacting exclusively (Schmeme 5).The glycosyl acceptor 8 was prepared from 9 by reductive opening of the dioxolane ring (Scheme 3).The donors 26-28 were prepared from the same precursor 9 via the hemiacetal 25.To obtain 9, the known 10 was de-N-acetylated (-> 18), treated with phthalic anhydride (-> 19), and benzylated, leading to 9 and 23 (Schemes 2 and 3).Saponification of 23, followed by acetylation also gave 9.Depending upon the conditions, acetylation of 19 yielded a mixture of 20 and 21 or exclusively 20.Deacetylation of 20 led to the hydroxyphthalimide 22.De-N-acetylation of the 3-O-benzylated α-D-glycosides 11 and 15, which were both obtained from 10, was very sluggish and accompanied by partial reduction of the O-allyl to an O-propyl group (Scheme 2).The β-D-glycoside 30 behaved very similarly to 11 and 15.Reductive ring opening of 31, derived from 29, yielded the 3-O-acetylated acceptor 32, while the analogous reaction of the α-D-anomer 20 was accompanied by a rapid 3-O -> 4-O acyl migration (-> 34; Scheme 4).Reductive ring opening of 21 gave the diol 35.The triacetylated donors 38-40 were obtained from 20 by debenzylidenation, acetylation (-> 36), and deallylation (-> 37), followed by either acetylation (-> 38), treatment with Me3SiSEt (-> 39), or Cl3CCN (-> 40).
