Category: 10378-06-0

Wang, Shuo published the artcileCharacterization of two UDP-Gal:GalNAc-diphosphate-lipid β1,3-galactosyltransferases WbwC from Escherichia coli serotypes O104 and O5, Recommanded Product: (3aR,5R,6R,7R,7aR)-5-(Acetoxymethyl)-2-methyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]oxazole-6,7-diyl diacetate, the publication is Journal of Bacteriology (2014), 196(17), 3122-3133, 13 pp., database is CAplus and MEDLINE.

Escherichia coli displays O antigens on the outer membrane that play an important role in bacterial interactions with the environment. The O antigens of enterohemorrhagic E. coli O104 and O5 contain a Galβ1-3GalNAc disaccharide at the reducing end of the repeating unit. Several other O antigens contain this disaccharide, which is identical to the mammalian O-glycan core 1 or the cancer-associated Thomsen-Friedenreich (TF) antigen. The authors identified the wbwC genes responsible for the synthesis of the disaccharide in E. coli serotypes O104 and O5. To functionally characterize WbwC, an acceptor substrate analog, GalNAcα-diphosphate-phenylundecyl, was synthesized. WbwC reaction products were isolated by HPLC and analyzed by mass spectrometry, NMR, galactosidase and O-glycanase digestion and anti-TF antibody. The Galβ1-3GalNAcα linkage was synthesized, confirming WbwCECO104 and WbwCECO5 as UDP-Gal:GalNAcα-diphosphate-lipid β1,3-Gal-transferases. Sequence anal. revealed a conserved DxDD motif and mutagenesis showed the importance of these Asp residues in catalysis. The purified enzymes require divalent cations (Mn²⁺) for activity and are specific for UDP-Gal and GalNAc-diphosphate lipid substrates. WbwC was inhibited by bis-imidazolium salts having aliphatic chains of 18 to 22 carbons. This work will help to elucidate mechanisms of polysaccharide synthesis in pathogenic bacteria and provide technol. for vaccine synthesis.

Journal of Bacteriology published new progress about 10378-06-0. 10378-06-0 belongs to esters-buliding-blocks, auxiliary class Other Aliphatic Heterocyclic,Chiral,Ester,Inhibitor,Inhibitor, name is (3aR,5R,6R,7R,7aR)-5-(Acetoxymethyl)-2-methyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]oxazole-6,7-diyl diacetate, and the molecular formula is C8H7NO4, Recommanded Product: (3aR,5R,6R,7R,7aR)-5-(Acetoxymethyl)-2-methyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]oxazole-6,7-diyl diacetate.

Referemce:
https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics

Wang, Shuo published the artcileCharacterization of two UDP-Gal:GalNAc-diphosphate-lipid β1,3-galactosyltransferases WbwC from Escherichia coli serotypes O104 and O5, Computed Properties of 10378-06-0, the publication is Journal of Bacteriology (2014), 196(17), 3122-3133, 13 pp., database is CAplus and MEDLINE.

Escherichia coli displays O antigens on the outer membrane that play an important role in bacterial interactions with the environment. The O antigens of enterohemorrhagic E. coli O104 and O5 contain a Galβ1-3GalNAc disaccharide at the reducing end of the repeating unit. Several other O antigens contain this disaccharide, which is identical to the mammalian O-glycan core 1 or the cancer-associated Thomsen-Friedenreich (TF) antigen. We identified the wbwC genes responsible for the synthesis of the disaccharide in E. coli serotypes O104 and O5. To functionally characterize WbwC, an acceptor substrate analog, GalNAcα-diphosphate-phenylundecyl, was synthesized. WbwC reaction products were isolated by high-pressure liquid chromatog. and analyzed by mass spectrometry, NMR, galactosidase and O-glycanase digestion, and anti-TF antibody. The results clearly showed that the Galβ1-3GalNAcα linkage was synthesized, confirming WbwCECO104 and WbwCECO5 as UDP-Gal:GalNAcα-diphosphate-lipid β1,3-Gal-transferases. Sequence anal. revealed a conserved DxDD motif, and mutagenesis showed the importance of these Asp residues in catalysis. The purified enzymes require divalent cations (Mn2+) for activity and are specific for UDP-Gal and GalNAc-diphosphate lipid substrates. WbwC was inhibited by bis-imidazolium salts having aliphatic chains of 18 to 22 carbons. This work will help to elucidate mechanisms of polysaccharide synthesis in pathogenic bacteria and provide technol. for vaccine synthesis.

Journal of Bacteriology published new progress about 10378-06-0. 10378-06-0 belongs to esters-buliding-blocks, auxiliary class Other Aliphatic Heterocyclic,Chiral,Ester,Inhibitor,Inhibitor, name is (3aR,5R,6R,7R,7aR)-5-(Acetoxymethyl)-2-methyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]oxazole-6,7-diyl diacetate, and the molecular formula is C12H20O6, Computed Properties of 10378-06-0.

Referemce:
https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics

Pujol, Anais M. published the artcileA sulfur tripod glycoconjugate that releases a high-affinity copper chelator in hepatocytes, Category: esters-buliding-blocks, the publication is Angewandte Chemie, International Edition (2012), 51(30), 7445-7448, S7445/1-S7445/24, database is CAplus and MEDLINE.

Th authors developed glycoconjugates 1 from a tripodal Cu¹ chelator L² derived from nitrilotriacetic acid (NTA) by an extension with three cysteines, which exhibits an affinity for Cu¹ as high as that of metallothioneins, and a ligand of the asialoglycoprotein receptor (ASGP-R), and the Cu-chelating property in vitro and efficiency in two hepatic cell lines were tested. The results showed that the glycoconjugate 1 can be considered as a vector delivering L², the active compound, at the right place to chelate excess Cu₁. For the Wilson’s disease patients, 1 could represent an interesting concept of a prodrug to be further developed.

Angewandte Chemie, International Edition published new progress about 10378-06-0. 10378-06-0 belongs to esters-buliding-blocks, auxiliary class Other Aliphatic Heterocyclic,Chiral,Ester,Inhibitor,Inhibitor, name is (3aR,5R,6R,7R,7aR)-5-(Acetoxymethyl)-2-methyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]oxazole-6,7-diyl diacetate, and the molecular formula is C14H19NO8, Category: esters-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics

Bernardes, Goncalo J. L. published the artcileDesign, synthesis and biological evaluation of carbohydrate-functionalized cyclodextrins and liposomes for hepatocyte-specific targeting, Formula: C14H19NO8, the publication is Organic & Biomolecular Chemistry (2010), 8(21), 4987-4996, database is CAplus and MEDLINE.

Targeting glycan-binding receptors is an attractive strategy for cell-specific drug and gene delivery. The C-type lectin asialo-glycoprotein receptor (ASGPR) is particularly suitable for liver-specific delivery due to its exclusive expression by parenchymal hepatocytes. In this study, we designed and developed an efficient synthesis of carbohydrate-functionalized β-cyclodextrins (βCDs) and liposomes for hepatocyte-specific delivery. For targeting of ASGPR, rhodamine B-loaded βCDs were functionalized with glycodendrimers. Liposomes were equipped with synthetic glycolipids containing a terminal d-GalNAc residue to mediate binding to ASGPR. Uptake studies in the human hepatocellular carcinoma cell line HepG2 demonstrated that βCDs and liposomes displaying terminal d-Gal/d-GalNAc residues were preferentially endocytosed. In contrast, uptake of βCDs and liposomes with terminal d-Man or D-GlcNAc residues was markedly reduced. The d-Gal/d-GalNAc-functionalized βCDs and liposomes presented here enable hepatocyte-specific targeting. Gal-functionalized βCDs are efficient mol. carriers to deliver doxorubicin in vitro into hepatocytes and induce apoptosis.

Organic & Biomolecular Chemistry published new progress about 10378-06-0. 10378-06-0 belongs to esters-buliding-blocks, auxiliary class Other Aliphatic Heterocyclic,Chiral,Ester,Inhibitor,Inhibitor, name is (3aR,5R,6R,7R,7aR)-5-(Acetoxymethyl)-2-methyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]oxazole-6,7-diyl diacetate, and the molecular formula is C14H19NO8, Formula: C14H19NO8.

Referemce:
https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics

Crasto, Curtis F. published the artcileA Practical method for preparation of β-glycosides of N-acetylglucosamine, SDS of cas: 10378-06-0, the publication is Tetrahedron Letters (2004), 45(25), 4891-4894, database is CAplus.

A mild and efficient method for preparation of GlcNAc derivatives by reaction of glycosyl acceptors with glycosyl oxazolines has been developed. The key feature is use of Yb(OTf)₃ as promoter, requiring moderate reaction times and equivalence stoichiometry. We anticipate application in the preparation of a wide range of derivatives of this biol. important class of building blocks.

Tetrahedron Letters published new progress about 10378-06-0. 10378-06-0 belongs to esters-buliding-blocks, auxiliary class Other Aliphatic Heterocyclic,Chiral,Ester,Inhibitor,Inhibitor, name is (3aR,5R,6R,7R,7aR)-5-(Acetoxymethyl)-2-methyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]oxazole-6,7-diyl diacetate, and the molecular formula is C14H19NO8, SDS of cas: 10378-06-0.

Referemce:
https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics

Matta, Khushi L. published the artcileSimple method for the synthesis of 2-acetamido-2-deoxy-β-D-galactopyranosides, Product Details of C14H19NO8, the publication is Carbohydrate Research (1973), 26(1), 215-18, database is CAplus.

Treatment of 2-acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-β-D- galactopyranose in CH2Cl2 with anhydrous FeCl3 gave 66% 2-methyl-(3,4,6-triO-acetyl-1,2-dideoxy-α-D-gal- actopyrano)-[2′ 1′:4,5]-2-oxazoline (I), which reacted readily with PhCH2OH and with 1,2,3-tri-O-benzoyl-α-D-galactose to give 65% benzyl β-glycoside derivative and 44% (1 → 6)-β-D-linked di- saccharide derivatives, resp.

Carbohydrate Research published new progress about 10378-06-0. 10378-06-0 belongs to esters-buliding-blocks, auxiliary class Other Aliphatic Heterocyclic,Chiral,Ester,Inhibitor,Inhibitor, name is (3aR,5R,6R,7R,7aR)-5-(Acetoxymethyl)-2-methyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]oxazole-6,7-diyl diacetate, and the molecular formula is C14H19NO8, Product Details of C14H19NO8.

Referemce:
https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics

Wu, Ying-Ta published the artcileA new N-acetylgalactosamine containing peptide as a targeting vehicle for mammalian hepatocytes via asialoglycoprotein receptor endocytosis, Formula: C14H19NO8, the publication is Current Drug Delivery (2004), 1(2), 119-127, database is CAplus and MEDLINE.

Galactoside-containing cluster ligands have high affinity for asialoglycoprotein receptors (ASGP-r), which are found in abundance in mammalian parenchymal liver cells. These ligands may be conjugated with a therapeutic drug to improve the efficiency of delivery to diseased liver cells. This report describes a new synthetic route towards clustering glycopeptides containing N-acetyl-D-galactosamine (GalNAc). The building block Fmoc-α-(ah-Ac₃GalNAc)-L-glutamate allowed access to the target compound YEEE(α-ah-GalNAc)₃, a structural mimic of YEE(ah-GalNAc)₃, via solid phase peptide synthesis (SPPS). Fatty acid, polylysine, fluorescein and biotin conjugates further demonstrate the facility of the described method. Using fluorescein labeling and ¹³¹I labeling, in vitro and in vivo assays confirmed that YEEE(α-ah-GalNAc)₃ possesses both specificity and affinity to the liver, similar to the agent YEE(ah-GalNAc)₃, which targets liver lesions. The synthesis described in this report represents a considerable improvement in synthesizing a ligand for ASGP-r by simplifying both the preparation of the starting material and the procedure for conjugating the galactosidase cluster to drugs.

Current Drug Delivery published new progress about 10378-06-0. 10378-06-0 belongs to esters-buliding-blocks, auxiliary class Other Aliphatic Heterocyclic,Chiral,Ester,Inhibitor,Inhibitor, name is (3aR,5R,6R,7R,7aR)-5-(Acetoxymethyl)-2-methyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]oxazole-6,7-diyl diacetate, and the molecular formula is C6H9BN2O2, Formula: C14H19NO8.

Referemce:
https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics

Hofmeister, Armin published the artcileSyntheses of Morpholine-Based Nucleotide Analogs for Hepatic siRNA Targeting and Stabilization, Category: esters-buliding-blocks, the publication is Journal of Medicinal Chemistry (2021), 64(10), 6838-6855, database is CAplus and MEDLINE.

A morpholine-based nucleotide analog was developed as a building block for hepatic siRNA targeting and stabilization. Attachment of an asialoglycoprotein-binding GalNAc ligand at the morpholine nitrogen was realized with different linkers. The obtained morpholino GalNAc scaffolds were coupled to the sense strand of a transthyretin-targeting siRNA and tested for their knockdown potency in vitro and in vivo. A clear structure-activity relationship was developed with regard to the linker type and length as well as the attachment site of the morpholino GalNAc moieties at the siRNA sense strand. Further, simple alkylation of the morpholine nitrogen led to a nucleotide analog, which increased siRNA stability, when used as a double 3′-overhang at the sense strand sequence. Combination of the best morpholino GalNAc building blocks as targeting nucleotides with an optimized stabilizing alkyl-substituted morpholine as 3′-overhangs resulted in siRNAs without any phosphorothioate stabilization in the sense strand and clearly improved the duration of action in vivo.

Journal of Medicinal Chemistry published new progress about 10378-06-0. 10378-06-0 belongs to esters-buliding-blocks, auxiliary class Other Aliphatic Heterocyclic,Chiral,Ester,Inhibitor,Inhibitor, name is (3aR,5R,6R,7R,7aR)-5-(Acetoxymethyl)-2-methyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]oxazole-6,7-diyl diacetate, and the molecular formula is C14H19NO8, Category: esters-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics

Ishida, Hideharu published the artcileSynthetic studies on sialoglycoconjugates. 94. Synthesis of 6′-GM2, a regioisomer of ganglioside GM2, for studying the mechanism of action of GM2 activator, HPLC of Formula: 10378-06-0, the publication is Carbohydrate Research (1997), 302(3-4), 223-227, database is CAplus and MEDLINE.

GM2 activator is a protein cofactor that assists β-hexosaminidase (HexA) in hydrolyzing the β-linked N-acetylgalactosamine (GalNAc) in ganglioside GM2. We report a synthesis of the regioisomer of ganglioside GM2, 6′-GM2, in which the GalNAc residue is linked, not to the 4-OH, but to the 6-OH of Gal to show that the resistance of GalNAc in GM2 to HexA is due to the specific structure of the GM2-epitope, β-D-GalNAc-(1→4)-α-Neu5Ac-(2→3)-β-D-Gal→.

Carbohydrate Research published new progress about 10378-06-0. 10378-06-0 belongs to esters-buliding-blocks, auxiliary class Other Aliphatic Heterocyclic,Chiral,Ester,Inhibitor,Inhibitor, name is (3aR,5R,6R,7R,7aR)-5-(Acetoxymethyl)-2-methyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]oxazole-6,7-diyl diacetate, and the molecular formula is C14H19NO8, HPLC of Formula: 10378-06-0.

Referemce:
https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics

Cui, Jingrong published the artcileStereocontrolled allylation of 2-amino-2-deoxy sugar derivatives by a free-radical procedure, Safety of (3aR,5R,6R,7R,7aR)-5-(Acetoxymethyl)-2-methyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]oxazole-6,7-diyl diacetate, the publication is Carbohydrate Research (1998), 309(4), 319-330, database is CAplus.

Preparative routes for anomerically specific 1-C-allylation of 2-amino-2-deoxy sugars have been evaluated in a comparative study of various N-substituents and aglycons as precursors for glycosyl radicals that effectively capture an allyl group from allyltributyltin. The crystalline triacetate of 3-(2-acetamido-2-deoxy-α-D-glucopyranosyl)-1-propene was obtained in 70% yield when 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranosyl chloride was treated with allyltributyltin under free-radical conditions, whereas the corresponding bromide led only to an oxazolidine derivative The 2-trifluoroacetamido 1-bromide analog of 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranosyl chloride was also an effective radical source, giving the 2-trifluoroacetamido analog in 60% yield. The free amino analog was conveniently obtained via the 2-p-methoxybenzylideneamino 1-bromide analog of 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranosyl chloride. Use of 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl bromide as radical precursor allowed stereospecific access to β-1-C-allyl derivatives of the amino sugar. The crystalline galactosamine analog was obtained by using the galacto analog of 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranosyl chloride, but the corresponding manno chloride gave only an oxazoline product. The 1-C-allylated amino sugar derivatives are conformationally more mobile than derivatives not having a 1-C-linked substituent.

Carbohydrate Research published new progress about 10378-06-0. 10378-06-0 belongs to esters-buliding-blocks, auxiliary class Other Aliphatic Heterocyclic,Chiral,Ester,Inhibitor,Inhibitor, name is (3aR,5R,6R,7R,7aR)-5-(Acetoxymethyl)-2-methyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]oxazole-6,7-diyl diacetate, and the molecular formula is C14H19NO8, Safety of (3aR,5R,6R,7R,7aR)-5-(Acetoxymethyl)-2-methyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]oxazole-6,7-diyl diacetate.

Referemce:
https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics