1 edition of Synthesis of a thiosugar analogue of an N - linked oligosaccharide fragment found in the catalog.
Synthesis of a thiosugar analogue of an N - linked oligosaccharide fragment
R. P. Martin
|Statement||Richard Peter Martin ; supervised by D.A. Leigh.|
|Contributions||Leigh, D. A., Chemistry.|
Glycobiology has become a “hot” subject,2 a timely one for “Reflections.” The primary reason, I think, is illustrated in Fig.1, which shows the surface of an erythrocyte in outside the plasma membrane of this and nearly all cells is a coat of fuzzy material called the glycocalyx, consisting of a myriad of carbohydrate-rich molecules, polysaccharides, proteoglycans. MEDI Synthesis and immunological properties of oligosaccharide fragment derived from the cell wall of Bacillus anthracis: A diagnostic tool for anthrax. In ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY Vol.
Book Series Help; Contact Portal SYNLETT Parallel Synthesis of Oligosaccharide Conjugated Enediynes onto Silyl-linked Solid-Support Concise Synthesis of the C3-CFragment of the Antitumor Agent Laulimalide. Application of Jacobsen's HKR Reaction. The IC 50 value of acarbose (1) for ctMGAM ( ± n m) was ∼ times lower than that for ntMGAM (62 ± 14 n m). Similarly, the IC 50 for ctSI ( ± n m) was ∼ times lower than that for ntSI ( ± 18 n m). Therefore, acarbose shows selectivity for inhibition of ctMGAM and ctSI over the N-terminal subunits.
Understanding Biology Using Peptides: Proceedings of the 19th American Peptide Symposium highlights many of the recent developments in peptide science, with a particular emphasis on how these advances are being applied to basic problems in biology and medicine. Specific topics covered include novel. Jérémy Boilevin, Synthesis of lipid-linked oligosaccharide substrates and inhibtors of protein N-Glycosylation enzymes. Ricardo Visini, Cheminformatic and structural biology insights into small molecule fragments, ring systems and peptides. Runze He,
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The chemical synthesis of three analogues of the calicheamicin gamma (I)(1) 1 and esperamicin A(1B) 2 oligosaccharides is described in which the carbohydrate ring E is replaced by a basic side. The chemical synthesis of three analogues of the calicheamicin γ 1 I 1 and esperamicin A 1B 2 oligosaccharides is described in which the carbohydrate ring E is replaced by a basic side chain E′.
Our synthetic strategy begins with ABE′ fragment construction which possesses an unusual β N. By using an N,N-diacetylamino derivative of donoran improved yield (75%) of the corresponding hexasaccharide was achieved. Download: Download full-size image; Scheme Synthesis of a lipo-oligosaccharide from Haemophilus ducreyi.
Reprinted, with Cited by: 4. Carbohydrates May Be Linked to Proteins Through Asparagine (N-Linked) or Through Serine or Threonine (O-Linked) ResiduesIn glycoproteins, sugars are attached either to the amide nitrogen atom in the side chain of asparagine (termed an N-linkage) or to the oxygen atom in the side chain of serine or threonine (termed an O-linkage), as shown in Figure Cited by: 5.
In the first part of this review, a new and efficient strategy for the synthesis of the sugar chains of glycoproteins is described. For the synthesis of N-linked sugar chains, the core. Zhong-Wu Guo, Yoshiaki Nakahara and Tomoya Ogawa, A practical and efficient synthesis of complex-type biantennary heptasaccharide-asparagine conjugate, a key building block for the synthesis of complex N-linked glycopeptides, Tetrahedron Letters, /S(97).
The cytotoxic drug tunicamycin kills cells because it is a specific inhibitor of UDP- N -acetylglucosamine:dolichol phosphate N -acetylglucosamineP transferase (GPT), an enzyme that catalyzes the initial step of the biosynthesis of dolichol-linked oligosaccharides.
In the presence of tunicamycin, asparagine-linked glycoproteins made in the endoplasmic reticulum are not glycosylated with N. Here we report the synthesis of oligomers (mono- di- and trisaccharide) of carba-N-acetylmannosamineO-phosphate as candidates for stabilized analogues of the corresponding fragments of MenA capsular polysaccharide.
Each of the synthesized compounds contains a phosphodiester-linked aminopropyl spacer at its reducing end to allow for protein. In comparison, chemical synthesis offers exceptional flexibility. Natural and non-natural saccharide building blocks can be assembled with natural or non-natural linkages.
Although some enzymes will act on alternative substrates, chemical synthesis provides the means to generate any oligosaccharide, oligosaccharide analog, or glycoconjugate. Abstract. This chapter describes the assembly of uronic acid containing oligosaccharides and glycoconjugates. Two strategies are available to access these target molecules, namely a pre-glycosylation oxidation approach, in which uronic acid building blocks are used, and a post-glycosylation oxidation strategy, which employs an oxidation step after the assembly of the oligosaccharide chain.
JPHA JPA JPA JPHA JP H A JPH A JP HA JP A JP A JP A JP A JP A JP. A protocol for the synthesis of novel cyclic β-1,6-S-linked glucopyranosides is developed.
The key intermediate is a linear thiooligosaccharide bearing an iodo group at C-6 of the nonreducing sugar and a thioacetyl group at the anomeric center of the reducing end sugar. The crucial macrocyclization step was achieved through base-promoted intramolecular SN2 glycosylation in remarkably high.
The use of a serine-derived sulfamidate (Scheme 3a) based on previous methods, allows reaction with thiohexoses to create S-linked glycoaminoacids in water and this is a method that could potentially be adapted to convert N-terminal serines to glycosylcysteines in peptides, although some amino acid α-epimerization was noted and this may.
A synthesis of a chromogenic glycoside of the Salmonella anatum group E1 core trisaccharide is presented in which all three glycosidic bonds, a 1,2-cis-equatorial, a 1,2-trans-axial, and a 1,2-trans-equatorial linkage representing three of the four main classes of glycosidic bond, are formed with thioglycoside donors activated under a single set of conditions by the combination of 1.
Wilson JR, Williams D, Schachter H. The control of glycoprotein synthesis. N-acetyl-glucosamine linkage to a mannose residue as a signal for the attachment of L-fucose to the asparagine-linked N-acetylglucosamine of glycopeptide from α 1-acid glycoprotein. Biochem Biophys Res Commun ; – PubMed Google Scholar.
Oligosaccharide synthesis was performed via H-phosphonate chemistry starting from tetrasaccharide building block 77 and using a [4+4] iterative elongation strategy.
Tetrameric, hexameric, octameric and decameric PRP fragments were obtained using this iterative approach, followed by the introduction of phosphodiester-linked spacer.
Phospholipase A (PLA) activity, as measured by the accumulation of 14C-lysophosphatidylcholine in leaves of tomato plants, increased rapidly and systemically in response to wounding. The increase in PLA activity in the systemic unwounded leaves was biphasic in wild-type tomato plants, peaking at 15 min and again at 60 min, but the second peak of activity was absent in transgenic prosystemin.
Glycosylation is one of the most common post-translational modifications in eukaryotic cells and plays important roles in many biological processes, such as the immune response and protein quality control systems.
It has been notoriously difficult to study glycoproteins by X-ray crystallography since the glycan moieties usually have a heterogeneous chemical structure and conformation, and are.
synthesis binding fig acid scheme cell cells carbohydrate inhibitors activity cancer oligosaccharides biol structure groups linked synthetic oligosaccharide analysis glycosyl sugar sialyl protein inhibition soc ligands.
Since the kD fragment drops from the predicted molecular weight of glycosylated TCR-α, it is likely to also be glycosylated.
In fact, treatment with N-glycanase resulted in a drop in molecular weight consistent with at least one N-linked oligosaccharide (data not shown).
If the address matches an existing account you will receive an email with instructions to retrieve your username.In eukaryotic organisms, N-glycosylation is achieved by co- or posttranslational attachment of the preassembled core glycan, Glc 3 Man 9 GlcNAc 2-Asn (Glc, Man, and GlcNAc refer to Glc, Man, and N-acetylglucosamine) to the γ-amido group of a specific Asn in the glycosylation consensus sequence Asn-X-Ser/ reaction is catalyzed by an oligosaccharyltransferase multisubunit complex in the.Isomaltulose synthase (sucrose, EC ) converts surcrose to isomaltulose (6-O- alpha -D-glucopyranosyl-D-fructofuranose).
The enzyme has been isolated from Erwinia rhapontici and an additional bacterial isolate 68J. Also disclosed are methods for converting sucrose to isomaltulose, transformation of plants and bacteria such that they convert surcrose, methods of detection of.