130539-43-4 | - Page 3 of 4 - Indole Building Blocks

Ledvina, Miroslav et al. published their research in Collection of Czechoslovak Chemical Communications in 1998 |CAS: 130539-43-4

The Article related to glycopeptide gmdp analog preparation, Amino Acids, Peptides, and Proteins: Poly(Amino Acids) and Peptides and other aspects.Category: indole-building-block

On April 30, 1998, Ledvina, Miroslav; Zyka, Daniel; Jezek, Jan; Trnka, Tomas; Saman, David published an article.Category: indole-building-block The title of the article was New effective synthesis of (N-acetyl- and N-stearoyl-2-amino-2-deoxy-β-D-glucopyranosyl)-(1→4)-N-acetylnormuramoyl-L-2-aminobutanoyl-D-isoglutamine, analogs of GMDP with immunopotentiating activity. And the article contained the following:

Et 3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (5), prepared by benzylation of Et 2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside, was transformed by reaction with bromine into 3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl bromide (6). Thioglycoside 5 in the presence of Me triflate and glycosyl bromide 6 in the presence of silver triflate were used as glycosyl donors for condensation with benzyl 2-acetamido-3-O-allyl-6-O-benzyl-2-deoxy-α-D-glucopyranoside, to give benzyl 2-acetamido-3-O-allyl-6-O-benzyl-4-O-(3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-2-deoxy-α-D-glucopyranoside (8). Its reductive dephthaloylation with NaBH4/AcOH afforded benzyl 2-acetamido-3-O-allyl-4-O-(2-amino-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-6-O-benzyl-2-deoxy-α-D-glucopyranoside (11). Compound 11 was N-acylated to give benzyl 2-acetamido-4-O-(2-acylamino-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-3-O-allyl-6-O-benzyl-2-deoxy-α-D-glucopyranosides. These compounds were converted into corresponding benzyl 2-acetamido-4-O-(2-acylamino-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-6-O-benzyl-3-O-carboxymethyl-2-deoxy-α-D-glucopyranosides which, by condensation with H-L-Abu-D-isoGln(OBzl) followed by hydrogenolysis of protective benzyl groups, furnished the title glycopeptides. Intramol. O→N migration of the allyl protecting group followed by its reduction to the Pr residue by reaction of compound 8 with hydrazine or hydrazinium acetate, to give benzyl 2-acetamido-4-O-(3,4,6-tri-O-benzyl-2-deoxy-2-propylamino-β-D-glucopyranosyl)-6-O-benzyl-2-deoxy-α-D-glucopyranoside, is also described. The experimental process involved the reaction of Ethyl 2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-thio-beta-D-glucopyranoside(cas: 130539-43-4).Category: indole-building-block

The Article related to glycopeptide gmdp analog preparation, Amino Acids, Peptides, and Proteins: Poly(Amino Acids) and Peptides and other aspects.Category: indole-building-block

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Nagorny, Pavel et al. published their research in Journal of the American Chemical Society in 2009 |CAS: 130539-43-4

The Article related to hfsh glycopeptide dodecasaccharide chitobiose preparation sinay glycosidation lansbury aspartylation, Amino Acids, Peptides, and Proteins: Poly(Amino Acids) and Peptides and other aspects.Synthetic Route of 130539-43-4

On April 29, 2009, Nagorny, Pavel; Fasching, Bernhard; Li, Xuechen; Chen, Gong; Aussedat, Baptiste; Danishefsky, Samuel J. published an article.Synthetic Route of 130539-43-4 The title of the article was 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. And the article contained the following:

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 FSH (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 chem. 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 and 24. The experimental process involved the reaction of Ethyl 2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-thio-beta-D-glucopyranoside(cas: 130539-43-4).Synthetic Route of 130539-43-4

Landstroem, Jens et al. published their research in Organic & Biomolecular Chemistry in 2012 |CAS: 130539-43-4

The Article related to hen egg lysozyme carbohydrate ligand solution structure, Enzymes: Substrates-Cofactors-Inhibitors-Activators-Coenzymes-Products and other aspects.Reference of Ethyl 2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-thio-beta-D-glucopyranoside

Landstroem, Jens; Bergstroem, Maria; Hamark, Christoffer; Ohlson, Sten; Widmalm, Goeran published an article in 2012, the title of the article was Combining weak affinity chromatography, NMR spectroscopy and molecular simulations in carbohydrate-lysozyme interaction studies.Reference of Ethyl 2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-thio-beta-D-glucopyranoside And the article contains the following content:

By examining the interactions between the protein hen egg-white lysozyme (HEWL) and com. available and chem. synthesized carbohydrate ligands using a combination of weak affinity chromatog. (WAC), NMR spectroscopy and mol. 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, mol. docking and mol. 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. Intermol. hydrogen bonding and CH/π-interactions form the basis of the protein-ligand complexes in a way characteristic of carbohydrate-protein interactions. Mol. dynamics simulations with explicit water mols. 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 anal. 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 chem. 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 experimental process involved the reaction of Ethyl 2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-thio-beta-D-glucopyranoside(cas: 130539-43-4).Reference of Ethyl 2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-thio-beta-D-glucopyranoside

Nilsson, Kurt G. I. et al. published their patent in 1997 |CAS: 130539-43-4

The Article related to cellobiose derivative synthesis bullera glucosidase, Fermentation and Bioindustrial Chemistry: Pharmaceuticals (Including Nutrients) and other aspects.SDS of cas: 130539-43-4

On January 30, 1997, Nilsson, Kurt G. I. published a patent.SDS of cas: 130539-43-4 The title of the patent was Method of producing derivatives of β-D-glucosyl-1,4-N-acetyl-β-D-glucose. And the patent contained the following:

Disclosed is a method of producing a compound which contains the G1cβ1-4G1cN structure involving reacting ≥1 donor substance G1cβOR where R is an organic group, and ≥1 acceptor substance which is a glucopyranosamino derivative having the formula G1cNR”-R”’, wherein NR” is an azido, 2-N-acetyl-, 2-N-phthalimido, or an organic group bound to the 2-N-group of glucosamine, wherein R”’ is a glycosidically bound fluoro or is an O-, C-, N- or S-glycosidically bound aliphatic or aromatic compound, with the optional proviso that if NR” is NHAc then R”’ is not OH and if NR” is not NHAc then R”’ may be OH, in the presence of Bullera singularis or an enzyme commission (E.C.) group 3.2 glycosidase of essentially the same structure as an E.C. group 3.2 glucosidase obtained from B. singularis to form the G1cβ1-4G1cN derivative; and optionally isolating the compound which contains the G1cβ1-4G1cN structure. The experimental process involved the reaction of Ethyl 2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-thio-beta-D-glucopyranoside(cas: 130539-43-4).SDS of cas: 130539-43-4

The Article related to cellobiose derivative synthesis bullera glucosidase, Fermentation and Bioindustrial Chemistry: Pharmaceuticals (Including Nutrients) and other aspects.SDS of cas: 130539-43-4

Nilsson, Kurt et al. published their patent in 1995 |CAS: 130539-43-4

The Article related to lactosamine derivative production lactose transglycosylation galactosidase, Fermentation and Bioindustrial Chemistry: Pharmaceuticals (Including Nutrients) and other aspects.Application In Synthesis of Ethyl 2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-thio-beta-D-glucopyranoside

On July 13, 1995, Nilsson, Kurt published a patent.Application In Synthesis of Ethyl 2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-thio-beta-D-glucopyranoside The title of the patent was Method of producing derivatives of lactosamine. And the patent contained the following:

Disclosed is a method of producing compounds with β1-4 linkage which contains the lactosamine structure involving reacting ≥1 donor substance GalβOR where R is an organic group, and ≥1 acceptor substance which is a glucopyranosamino derivative having the formula GlcNR’-R”, wherein NR’ is an azido, 2-N-acetyl-, 2-N-phthalimido, or an organic group bound to the 2-N group of glucosamine, wherein R” is a glycosidically bound F- or is an O-, C-, N-, or S- glycosidically bound aliphatic or aromatic compound, with the proviso that if NR’ is NHAc then R” is not OH and if NR’ is not NHAc then R” may be OH, in the presence of Bullera singularis or an E.C. group 3.2 glycosidase of essentially the same structure as an E.C. group 3.2 glycosidase obtained from B. singularis to form the lactosamine derivative; and optionally isolating the compound with β1-4 linkage which contains the lactosamine structure. The experimental process involved the reaction of Ethyl 2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-thio-beta-D-glucopyranoside(cas: 130539-43-4).Application In Synthesis of Ethyl 2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-thio-beta-D-glucopyranoside

Blixt, Ola et al. published their research in Journal of Organic Chemistry in 2001 |CAS: 130539-43-4

The Article related to oligogalactoside preparation escherichia recombinant fusion protein, dna sequence gale gene, Fermentation and Bioindustrial Chemistry: Pharmaceuticals (Including Nutrients) and other aspects.Recommanded Product: 130539-43-4

On April 6, 2001, Blixt, Ola; Brown, Jillian; Schur, Melissa J.; Wakarchuk, Warren; Paulson, James C. published an article.Recommanded Product: 130539-43-4 The title of the article was Efficient Preparation of Natural and Synthetic Galactosides with a Recombinant β-1,4-Galactosyltransferase-/UDP-4′-Gal Epimerase Fusion Protein. And the article contained the following:

The numerous biol. roles of LacNAc-based oligosaccharides have led to an increased demand for these structures for biol. studies. In this report, an efficient route for the synthesis of β-galactosides using a bacterial β-4-galactosyltransferase/-UDP-4′-gal-epimerase fusion protein is described. The lgtB gene from Neisseria meningitidis and the galE gene from Streptococcus thermophilus were fused and cloned into an expression vector pCW. The fusion protein transfers galactose to a variety of different glucose- and glucosamine-containing acceptors, and utilizes either UDP-galactose or UDP-glucose as donor substrates. A crude lysate from Escherichia coli expressing the fusion protein is demonstrated to be sufficient for the efficient preparation of galactosylated oligosaccharides from inexpensive UDP-glucose in a multigram scale. Lysates containing the fusion protein are also found to be useful in the production of more complex oligosaccharides in coupled reaction mixtures , e.g., in the preparation of sialosides from N-acetylglucosamine. Thus, bacterially expressed fusion protein is well suited for the facile and economic preparation of natural oligosaccharides and synthetic derivatives based on the lactosamine core. The experimental process involved the reaction of Ethyl 2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-thio-beta-D-glucopyranoside(cas: 130539-43-4).Recommanded Product: 130539-43-4

Seifert, Joachim et al. published their patent in 2003 |CAS: 130539-43-4

The Article related to heparinoid synthon uronate pentasaccharide preparation glycosylation protecting group, uronate heparin oligosaccharide preparation monosaccharide disaccharide trisaccharide and other aspects.Reference of Ethyl 2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-thio-beta-D-glucopyranoside

On March 20, 2003, Seifert, Joachim; Singh, Latika; Ramsdale, Tracie Elizabeth; West, Michael Leo; Drinnan, Nicholas Barry published a patent.Reference of Ethyl 2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-thio-beta-D-glucopyranoside The title of the patent was Synthetic heparin pentasaccharides via glycosylation reaction using different protecting groups. And the patent contained the following:

Synthetic monosaccharides, disaccharides, trisaccharides, tetrasaccharides and pentasaccharides for use in the preparation of synthetic heparinoids. Thus, heparin pentasaccharide I (R1 = SO3Na) was prepared via glycosylation reaction using different protecting groups. The experimental process involved the reaction of Ethyl 2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-thio-beta-D-glucopyranoside(cas: 130539-43-4).Reference of Ethyl 2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-thio-beta-D-glucopyranoside

Minuth, Tobias et al. published their research in European Journal of Organic Chemistry in 2009 |CAS: 130539-43-4

The Article related to amino glycoside preparation structure property conformation catalysis oxazoline cyclopropanation, structure property conformation catalysis oxazoline ligand steric electronic and other aspects.Electric Literature of 130539-43-4

On March 31, 2009, Minuth, Tobias; Irmak, Mustafa; Groschner, Annika; Lehnert, Tobias; Boysen, Mike M. K. published an article.Electric Literature of 130539-43-4 The title of the article was Sweets for catalysis – facile optimization of carbohydrate-based bis(oxazoline) ligands. And the article contained the following:

A new type of carbohydrate-based bis(oxazoline) ligands was prepared from inexpensive D-glucosamine and tested in asym. cyclopropanation reactions. For optimization, modified ligands with 3-O substituents of varying size and electronic properties were prepared as well as a 3-OH unprotected and a perpivaloylated derivative All new ligands were tested in asym. cyclopropanation, revealing a strong dependence of enantioselectivity on steric demand and electronic properties of the 3-O residue. Also, a significant influence of the pyranose conformation, which is determined by the presence or absence of the cyclic acetal group, was observed Thus, it was easily possible to tune the new carbohydrate bis(oxazoline) ligands to a given reaction. The experimental process involved the reaction of Ethyl 2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-thio-beta-D-glucopyranoside(cas: 130539-43-4).Electric Literature of 130539-43-4

Seifert, Joachim et al. published their patent in 2015 |CAS: 130539-43-4

The Article related to heparinoid synthon uronate pentasaccharide preparation glycosylation protecting group, uronate heparin oligosaccharide preparation monosaccharide disaccharide trisaccharide and other aspects.Name: Ethyl 2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-thio-beta-D-glucopyranoside

On December 22, 2015, Seifert, Joachim; Singh, Latika; Ramsdale, Tracie Elizabeth; West, Michael Leo; Drinnan, Nicholas Barry published a patent.Name: Ethyl 2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-thio-beta-D-glucopyranoside The title of the patent was Synthetic heparin pentasaccharides via glycosylation reaction using different protecting groups. And the patent contained the following:

Preparation of synthetic monosaccharides, disaccharides I, wherein X is from the group consisting of a hydroxyl group; thioalkyl, thioaryl, halogen, trichloroacetimidoyl, and ‘butyldiphenylsilyloxy, and wherein the stereochem. may be α or β; R1 is 4-methoxyphenyl, benzyl, substituted benzyl groups, alkylacyl, arylacyl, alkylarylacyl, substituted alkylacyl, substituted arylacyl, substituted alkylarylacyl, carbonate protecting groups; R2 is 4-methoxyphenyl, alkylacyl, arylacyl, alkylarylacyl, substituted alkylacyl, substituted arylacyl, substituted alkylarylacyl protecting group, carbonate protecting groups, carbamate protecting groups, or alkenyl; R3 is Me, alkyl, alkenyl, benzyl and substituted benzyl; R4 is azido, substituted amine; R5 is benzyl, substituted benzyl protecting group, allyl, allyloxycarbonyl; R4 and R5 independently can combine together to form a cyclic carbamate; and, trisaccharides, tetrasaccharides and pentasaccharides; R6 is benzyl; R7 is benzoyl, arylacyl protecting group, alkylarylacyl protecting group, substituted alkylacyl protecting group, 4-chlorobenzoyl, substituted arylacyl protecting group, substituted alkylarylacyl protecting group, allyloxycarbonyl, ethoxycarbonyl, tertbutoxycarbonyl, carbonate protecting groups, t-butyldiphenylsilyl, allyl, methoxymethyl, methoxyethyl, were prepared for use in the preparation of synthetic heparinoids. Thus, heparin pentasaccharide II was prepared via glycosylation reaction using different protecting groups. The experimental process involved the reaction of Ethyl 2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-thio-beta-D-glucopyranoside(cas: 130539-43-4).Name: Ethyl 2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-thio-beta-D-glucopyranoside

The Article related to heparinoid synthon uronate pentasaccharide preparation glycosylation protecting group, uronate heparin oligosaccharide preparation monosaccharide disaccharide trisaccharide and other aspects.Name: Ethyl 2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-thio-beta-D-glucopyranoside

Wawryszyn, Mirella et al. published their research in European Journal of Organic Chemistry in 2018 |CAS: 130539-43-4

The Article related to cyclooctyne amino acid glycosylation glycoprotein oligosaccharide synthesis antibody, azido glycan protein synthesis oligosaccharide glycoprotein glycosylation cyclooctyne and other aspects.Computed Properties of 130539-43-4

Wawryszyn, Mirella; Sauter, Paul F.; Nieger, Martin; Koos, Martin R. M.; Koehler, Christine; Luy, Burkhard; Lemke, Edward A.; Braese, Stefan published an article in 2018, the title of the article was Synthesis of Azido-Glycans for Chemical Glyco-modification of Proteins.Computed Properties of 130539-43-4 And the article contains the following content:

Chem. produced, accurately linkable oligosaccharides are of importance for the synthesis of neo-glycoproteins. On the route to high-mannose type N-glycans, we present a convenient synthesis of several glycans bearing an azide moiety at the reducing end. An azido-glycan core structure as valuable precursor was modified into the protected N-glycan pentasaccharide core structure and the possibility of modular attachment of different antenna was demonstrated through synthesis of a pentamannose donor and glycosylation with the core structure. The azido function allows for chem. ligation with modified proteins featuring noncanonical cyclooctyne amino acids, providing access to customized glyco-patterns of glycoproteins, e.g., of antibodies that are of high interest for biopharmaceutical applications. The experimental process involved the reaction of Ethyl 2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-thio-beta-D-glucopyranoside(cas: 130539-43-4).Computed Properties of 130539-43-4