Category: 130539-43-4

On January 15, 2004, Seeberger, Peter H.; Hewitt, Michael C.; Snyder, Daniel published a patent.Formula: C16H19NO6S The title of the patent was Solid-phase and solution-phase synthesis of glycosylphosphatidylinositol glycans. And the patent contained the following:

One aspect of the present invention relates to solution-phase synthesis approaches to glycosylphosphatidylinositol (GPI) I, wherein, n is 1-4; R represents independently for each occurrence H, alkyl, aryl, CH2-aryl, C(O)-alkyl, C(O)-aryl, or Si(alkyl)3; R1 and R2 are independently H, CH2-aryl, C(O)-alkyl, C(O)-aryl, Si(alkyl)3; or R1 and R2 taken together are C(CH3)2, P(O)OH, or P(O)OR5; R3 is amino, N3, or NH3X; R4 represents independently for each occurrence H, alkyl, aryl, CH2-aryl, C(O)- alkyl, C(O)-aryl, Si(alkyl)3, or P(O)(OR5)2; R5 represents independently for each occurrence H, Li+, Na+, K+, Rb+, Cs+, aryl, or an optionally substituted alkyl group; and X is a halogen, alkyl carboxylate, or aryl carboxylate. Another aspect of the present invention relates to key building blocks, and syntheses thereof, useful for GPI assembly. Yet another aspect of the invention relates to an automated method for the synthesis of GPIs and fragments thereof. The synthesis of a pseudo-hexasaccharide glycosylphosphatidylinositol has been reduced to practice, both in solution and using a combination of solution and automated solid-phase methodologies. The material made in solution was covalently attached to a protein carrier and used to vaccinate mice. Inoculated mice were substantially protected against a subsequent challenge with Plasminodium parasites. This discovery further implicates GPI as the dominant toxin in malaria infections, and lays the groundwork for future trials in human volunteers. Combinations of solution and automated solid-phase synthetic methodologies will see continued usage in this context, and are expected to lead to the rapid generation of more potent vaccines for malaria and other maladies. 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).Formula: C16H19NO6S

The Article related to glycosylphosphatidylinositol oligosaccharide glycan solid phase synthesis vaccine human, Carbohydrates: Alditols, Cyclitols, Glycerides and other aspects.Formula: C16H19NO6S

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

On October 22, 2001, Misra, A. K.; Fukuda, M.; Hindsgaul, O. published an article.COA of Formula: C16H19NO6S The title of the article was Efficient synthesis of lactosaminylated core-2 O-glycans. And the article contained the following:

A series of lactosaminylated oligosaccharides found in mucin type O-glycans was synthesized using a generalized block strategy. The synthesis involved the addition of a protected lactosamine donor to a partially protected T-disaccharide derivative The nonreducing galactose residues of the deblocked oligosaccharide products could be removed by β-galactosidase from jack bean to produce the corresponding GlcNAc terminated compounds A series of tri- to hexasaccharides was thus efficiently produced. 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).COA of Formula: C16H19NO6S

The Article related to mucin glycan aminodeoxy oligosaccharide preparation galactosidase, lactosaminyl oligosaccharide preparation glycosylation, Carbohydrates: Amines and other aspects.COA of Formula: C16H19NO6S

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

Traboni, Serena; Bedini, Emiliano; Giordano, Maddalena; Iadonisi, Alfonso published an article in 2015, the title of the article was Three Solvent-Free Catalytic Approaches to the Acetal Functionalization of Carbohydrates and Their Applicability to One-Pot Generation of Orthogonally Protected Building Blocks.SDS of cas: 130539-43-4 And the article contains the following content:

Three alternative protocols were developed to carry out the selective installation of acetal groups on carbohydrates and polyols under mildly acidic, solvent-free conditions. One protocol is based on a diol/aldehyde condensation at room temperature, with an acetolysis process serving for the activation of the carbonyl component. A second approach is based on an orthoester-mediated activation of the carbonyl component at high temperature The third protocol is instead entailing a transacetalation mechanism. Combination of these methods allows a wide set of acetal-protected building blocks to be accessed in short times under very simple exptl. conditions working under air. The scope of the latter two approaches was also extended to unusual one-pot synthetic sequences leading to concomitant Fischer glycosidation/acetal protection of reducing sugars. 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 condensation transacetalation glycosylation catalyst glycoside preparation, Carbohydrates: Glycosides and other aspects.SDS of cas: 130539-43-4

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

On March 31, 2003, Sarkar, Kakali; Mukherjee, Indrani; Roy, Nirmolendu published an article.Computed Properties of 130539-43-4 The title of the article was Synthesis of the trisaccharide repeating unit of the O-antigen related to the enterohemorrhagic Escherichia coli type O26:H. And the article contained the following:

L-Fucose was converted to the 2-azido-2-deoxy-L-fucose derivative, which together with the monosaccharide synthons prepared from L-rhamnose and D-glucosamine hydrochloride were utilized for the synthesis of the p-ethoxyphenyl glycoside of the trisaccharide repeating unit of the antigen from enterohemorrhagic Escherichia coli type O26:H. 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

The Article related to fucopyranosyl glucopyranosyl rhamnopyranoside trisaccharide synthesis repeating unit escherichia coli, trisaccharide repeating unit synthesis antigen escherichia coli, Carbohydrates: Amines and other aspects.Computed Properties of 130539-43-4

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

On April 26, 2004, Cirla, Alessandra; McHale, Angela R.; Mann, John published an article.HPLC of Formula: 130539-43-4 The title of the article was Synthesis of analogues of calicheamicin and neocarzinostatin chromophore. And the article contained the following:

The work presents a synthetic route to the CD ring of calicheamicin and in the case of neocarzinostatin an approach to a functionalized cyclopentane-1,3-diol containing the naturally occurring naphthoate and a glucosamine motif. In the case of the NCS derivative some biol. activity (cytotoxicity) was observed 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).HPLC of Formula: 130539-43-4

The Article related to cyclopentane diol calicheamicin analog preparation anticancer, neocarzinostatin chromophore preparation anticancer, glucosamine cyclopentane diol preparation, Carbohydrates: Amines and other aspects.HPLC of Formula: 130539-43-4

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

On January 31, 1998, Kajihara, Yasuhiro; Kodama, Hisashi; Endo, Tsuyoshi; Hashimoto, Hironobu published an article.Recommanded Product: 130539-43-4 The title of the article was Novel features of acceptor recognition by β-(1â†?)-galactosyltransferase. And the article contained the following:

In order to understand how β-(1â†?)-galactosyltransferase recognizes its glycosyl acceptor, substrate specificities were investigated using synthetic 2-acetamido-2-deoxy-D-glucopyranose (N-acetylglucosamine) derivatives in which the 1-, 2-, 3-, 4-, and 6-positions were systematically substituted. The hydroxyl groups at the 3-, 4-, and 6-positions were substituted by fluoride, thiol or hydrogen. For modification of the 2- position, the acetamido group was converted to ethylamino-, N-methylacetamido- and acetyloxy groups. For the anomeric position, several sugar residues were introduced as the aglycon of N-acetylglucosaminide. Galactose transfer assay using synthetic N-acetylglucosamine derivatives indicated that both the acetamido group and the 4-hydroxyl group were essential for binding of N-acetylglucosamine toward the β-(1â†?)-galactosyltransferase. The assay also showed that the N-acetylglucosamine having a large substitution at the 6-position can be recognized as an acceptor. It is suggested that in this case the bulky substituent is positioned away from the catalytic site or out of enzyme. Since the 2-acetamido and the 4-hydroxyl group are essential for recognition, the side composed of the 2, 3, and 4-positions may face the acceptor-binding site. 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

The Article related to acetamidodeoxyglucopyranose substrate specificity galactosyltransferase, galactosyltransferase glycosyl acceptor recognition, Carbohydrates: Amines and other aspects.Recommanded Product: 130539-43-4

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

Seeberger, Peter H.; Baumann, Michael; Zhang, Guangtao; Kanemitsu, Takuya; Swayze, Eric E.; Hofstadler, Steven A.; Griffey, Richard H. published an article in 2003, the title of the article was Synthesis of neomycin analogs to investigate aminoglycoside-RNA interactions.Application In Synthesis 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:

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 different positions and conformations around the pyranose ring was utilized in the assembly of oligosaccharides. These aminoglycoside analogs were analyzed for their RNA-binding capacity using a high throughput mass spectroscopy assay. 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

The Article related to deoxystreptamine neomycin analog preparation rna binding, aminoglycoside oligosaccharide analog preparation rna binding, Carbohydrates: Amines 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

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

On August 15, 1990, El-Sokkary, Ramadan I.; Silwanis, Basim Azmy; Nashed, Mina A.; Paulsen, Hans published an article.Electric Literature of 130539-43-4 The title of the article was Standardized intermediates for oligosaccharide synthesis: convenient preparation of 2-amino-2-deoxy-D-glucose derivatives and their conversion into the D-galactose analogs. And the article contained the following:

Treating tetraacetate I (R = Ac, NPhth = phthalimido) with allyl alc. in CH2Cl2 containing FeCl3 gave I (R = CH2:CHCH2O) which was deacetylated by NaOMe-MeOH followed by benzoylation with BzCl to give 95.8% phthalimido derivative II. The latter was treated with (CF3SO2)2O in CH2Cl2 to give an intermediate 4-triflate which was converted by NaNO2-DMF to 86% galactopyranoside III, a useful glycosyl donor for oligosaccharide synthesis. 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

The Article related to oligosaccharide intermediate, amidodeoxyglucose, aminodeoxygalactose, glucose amino deoxy, galactose amino deoxy, Carbohydrates: Amines and other aspects.Electric Literature of 130539-43-4

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

On July 2, 2010, Kamkhachorn, Teerada; Parameswar, Archana R.; Demchenko, Alexei V. published an article.Category: indole-building-block The title of the article was Comparison of the Armed/Disarmed Building Blocks of the D-Gluco and D-Glucosamino Series in the Context of Chemoselective Oligosaccharide Synthesis. And the article contained the following:

A very elegant Fraser-Reid armed-disarmed approach recently expanded to the building blocks of the superarmed and superdisarmed series shows very high utility in chemoselective oligosaccharide synthesis. Although a number of studies dedicated to the chemoselective activation of 2-amino-2-deoxysugars have emerged, little remains known about how the reactivity of the armed/disarmed building blocks of the neutral sugars directly compares to that of their 2-aminosugar counterparts. A preliminary study of this comparative reactivity is presented. 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 oligosaccharide chemoselective synthesis, fraser reid armed disarmed glycosylation amino deoxysugar, Carbohydrates: Amines 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

On August 31, 2006, Gening, M. L.; Tsvetkov, Yu. E.; Pier, G. B.; Nifantiev, N. E. published an article.Application of 130539-43-4 The title of the article was The study of the reaction of terminated oligomerization in the synthesis of oligo-(β1-6)-glucosamines. And the article contained the following:

The applicability of terminated oligomerization to the synthesis of oligo-(β1-6)-glucosamines, fragments of the intercellular polysaccharide adhesion of staphylococci, was studied. The reactions of terminated oligomerization were carried out with mono-, di-, and trisaccharide monomers and N-protected aminopropanol; and mono- and disaccharides as terminating mols. were also attempted. The primary formation of cyclic products of monomer intramol. glycosylation was observed in almost all the reactions. Only the experiments with the monomer based on the disaccharide bromide under the conditions of the Helferich reaction led to reduced yields (30%) of the cyclic products. However, even in this case, the desired terminated oligosaccharides were generated in approx. 10% yield and mainly were the products of single glycosylation of the terminator by the monomer. These experiments allow the conclusion that, under the examined conditions, the reaction of terminated oligomerization could not result in the synthesis of oligo-glucosamines with a high mol. mass. 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 of 130539-43-4

The Article related to disaccharide trisaccharide oligosaccharide oligomerization glycosylation preparation glucosamine, Carbohydrates: Amines and other aspects.Application of 130539-43-4

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