Category: 10378-06-0

Wu, Jian published the artcileImproving the Antigenicity of sTn Antigen by Modification of Its Sialic Acid Residue for Development of Glycoconjugate Cancer Vaccines, Application 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 Bioconjugate Chemistry (2006), 17(6), 1537-1544, database is CAplus and MEDLINE.

Sialyl Tn (sTn) antigen is a sialylated disaccharide abundantly expressed by many tumors. To search for effective cancer immunotherapies based on sTn antigen, the authors designed and synthesized a series of unnatural N-acyl derivatives of sTn and studied their immunol. properties. For this purpose, an efficient method was developed to synthesize the natural and unnatural forms of sTn antigen and their protein conjugates. The resultant glycoconjugates were used to immunize C57BL/6 mice, and the immune response was assessed by ELISA. Whereas the keyhole limpet hemocyanin (KLH) conjugate of sTn elicited low levels of IgM antibodies, the KLH conjugates of N-iso-butanoyl sTn and N-phenylacetyl sTn, especially the latter, induced high titers of antigen-specific IgG antibodies, showing a T-cell-dependent response that is critical for the antitumor activity. The results suggest that the modified forms of sTn, especially N-phenylacetyl sTn, have improved antigenicity and promising immunol. properties for use as cancer vaccines.

Bioconjugate 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 C13H11NO, Application 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

Prakash, Thazha P. published the artcileTargeted delivery of antisense oligonucleotides to hepatocytes using triantennary N-acetyl galactosamine improves potency 10-fold in mice, Computed Properties of 10378-06-0, the publication is Nucleic Acids Research (2014), 42(13), 8796-8807, database is CAplus and MEDLINE.

Triantennary N-acetyl galactosamine (GalNAc, GN3), a high-affinity ligand for the hepatocyte-specific asialoglycoprotein receptor (ASGPR), enhances the potency of second-generation gapmer antisense oligonucleotides (ASOs) 6-10-fold in mouse liver. When combined with next-generation ASO designs comprised of short S-cEt (S-2′-O-Et-2′,4′-bridged nucleic acid) gapmer ASOs, ∼60-fold enhancement in potency relative to the parent MOE (2′-O-methoxyethyl RNA) ASO was observed GN3-conjugated ASOs showed high affinity for mouse ASGPR, which results in enhanced ASO delivery to hepatocytes vs. nonparenchymal cells. After internalization into cells, the GN3-ASO conjugate is metabolized to liberate the parent ASO in the liver. No metabolism of the GN3-ASO conjugate was detected in plasma suggesting that GN3 acts as a hepatocyte targeting prodrug that is detached from the ASO by metabolism after internalization into the liver. GalNAc conjugation also enhanced potency and duration of the effect of two ASOs targeting human apolipoprotein C-III and human transthyretin in transgenic mice. The unconjugated ASOs are currently in late stage clin. trials for the treatment of familial chylomicronemia and TTR-mediated polyneuropathy. The ability to translate these observations in humans offers the potential to improve therapeutic index, reduce cost of therapy and support a monthly dosing schedule for therapeutic suppression of gene expression in the liver using ASOs.

Nucleic Acids 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, Computed Properties of 10378-06-0.

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

Prakash, Thazha P. published the artcileSolid-phase synthesis of 5′-triantennary N-acetylgalactosamine conjugated antisense oligonucleotides using phosphoramidite chemistry, Formula: C14H19NO8, the publication is Bioorganic & Medicinal Chemistry Letters (2015), 25(19), 4127-4130, database is CAplus and MEDLINE.

A convenient solid-phase synthetic method was developed for assembling a triantennary N-acetylgalactosamine (GalNAc) cluster on the 5′-end of antisense oligonucleotide using phosphoramidite chem. Conjugation of the 5′-triantennary GalNAc cluster improved potency of the 14 mer ASO 7-fold in mice and more than 50 fold in hepatocytes. The synthetic approach described in this letter simplifies the synthesis of 5′-triantennary GalNAc cluster conjugated ASOs and helps understand the structure-activity relationship for targeting hepatocytes with oligonucleotide therapeutics.

Bioorganic & Medicinal Chemistry 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, Formula: C14H19NO8.

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

Mevel, Mathieu published the artcileChemical modification of the adeno-associated virus capsid to improve gene delivery, Product Details of C14H19NO8, the publication is Chemical Science (2020), 11(4), 1122-1131, database is CAplus and MEDLINE.

Gene delivery vectors based on adeno-associated virus (AAV) are highly promising due to several desirable features of this parent virus, including a lack of pathogenicity, efficient infection of dividing and non-dividing cells and sustained maintenance of the viral genome. However, the conclusion from clin. data using these vectors is that there is a need to develop new AAVs with a higher transduction efficiency and specificity for relevant target tissues. To overcome these limitations, we chem. modified the surface of the capsid of AAV vectors. These modifications were achieved by chem. coupling of a ligand by the formation of a thiourea functionality between the amino group of the capsid proteins and the reactive isothiocyanate motif incorporated into the ligand. This strategy does not require genetic engineering of the capsid sequence. The proof of concept was first evidenced using a fluorophore (FITC). Next, we coupled the N-acetylgalactosamine ligand onto the surface of the AAV capsid for asialoglycoprotein receptor-mediated hepatocyte-targeted delivery. Chem.-modified capsids also showed reduced interactions with neutralizing antibodies. Taken together, our findings reveal the possibility of creating a specific engineered platform for targeting AAVs via chem. coupling.

Chemical Science 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

Bouvet, Vincent R. published the artcileA Short and Economical Synthesis of Orthogonally Protected C-Linked 2-Deoxy-2-acetamido-α-D-galactopyranose Derivatives, 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 Organic Chemistry (2006), 71(9), 3619-3622, database is CAplus and MEDLINE.

A short and high-yielding synthesis has been devised to prepare C-linked 2-deoxy-2-acetamido-α-D-galactopyranose derivative (I). One of the main advantages of this approach is that it employs com. available and inexpensive D-glucosamine as the starting material. The key steps include a highly stereoselective C-allylation followed by epimerization of the C-4 hydroxyl group. Building block I and orthogonally protected C-linked 2-deoxy-2-acetamido-α-D-galactopyranose derivative were obtained in 44% overall yield (six steps) and 29% overall yield (eight steps), resp. This represents a significant improvement over previously reported syntheses.

Journal of Organic 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, 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