Synthesis of the 3’-O-sulfated TF antigen with a TEG-N₃ linker for glycodendrimersomes preparation to study lectin binding

• Mark Reihill,
• Hanyue Ma,
• Dennis Bengtsson and
• Stefan Oscarson

Beilstein J. Org. Chem. 2024, 20, 173–180, doi:10.3762/bjoc.20.17

• synthesis starting from unprotected N-acetylgalactosamine and a Lewis acid-promoted reaction starting from per-acetylated galactosamine were initially tested. As reported [11], the Fischer synthesis gives low yields and α-selectivity. The Lewis acid-promoted reaction, which had worked well to produce β

The role of chemistry in the success of oligonucleotides as therapeutics

• Pawan Kumar and
• Tom Brown

Beilstein J. Org. Chem. 2022, 18, 197–199, doi:10.3762/bjoc.18.22

• nucleotides massively improves the drug-like properties of oligonucleotides. However, their efficient delivery to the desired tissue/organ also needs to be addressed. Conjugation of oligonucleotides to GalNAc (N-acetylgalactosamine) has successfully been used for targeted delivery of oligonucleotides (both

Cationic oligonucleotide derivatives and conjugates: A favorable approach for enhanced DNA and RNA targeting oligonucleotides

• Mathias B. Danielsen and
• Jesper Wengel

Beilstein J. Org. Chem. 2021, 17, 1828–1848, doi:10.3762/bjoc.17.125

• ]. Notably, optimization of the therapeutic window of ASOs is closely related to improved delivery, and a variety of chemical strategies have been investigated in this context, such as ASO–lipid conjugates for improved endosomal escape [21], ASO–triantennary N-acetylgalactosamine (GalNAc) conjugates for

Simulating the enzymes of ganglioside biosynthesis with Glycologue

• Andrew G. McDonald and
• Gavin P. Davey

Beilstein J. Org. Chem. 2021, 17, 739–748, doi:10.3762/bjoc.17.64

• linear chain comprising of up to four monosaccharide units, containing glucose, galactose and N-acetylgalactosamine, to which are attached a variable number of sialic acid (N-acetylneuraminic acid) residues. The sialic acid content of the oligosaccharide, being anionic at pH 7, results in an overall

Semiautomated glycoproteomics data analysis workflow for maximized glycopeptide identification and reliable quantification

• Steffen Lippold,
• Arnoud H. de Ru,
• Jan Nouta,
• Peter A. van Veelen,
• Magnus Palmblad,
• Manfred Wuhrer and
• Noortje de Haan

Beilstein J. Org. Chem. 2020, 16, 3038–3051, doi:10.3762/bjoc.16.253

• mannose, Hex/H, 162.0528 Da), N-Acetylhexosamines (N-acetylglucosamine or N-acetylgalactosamine, HexNAc/N, 203.0794 Da), fucose (Fuc/F, 145.0579 Da), and sialic acid (N-acetylneuraminic acid, NeuAc/S, 291.0954 Da). The combinatorial possibilities of these building blocks and the variety of structural

A consensus-based and readable extension of Linear Code for Reaction Rules (LiCoRR)

• Benjamin P. Kellman,
• Yujie Zhang,
• Emma Logomasini,
• Eric Meinhardt,
• Karla P. Godinez-Macias,
• Austin W. T. Chiang,
• James T. Sorrentino,
• Chenguang Liang,
• Bokan Bao,
• Yusen Zhou,
• Sachiko Akase,
• Isami Sogabe,
• Thukaa Kouka,
• Elizabeth A. Winzeler,
• Iain B. H. Wilson,
• Matthew P. Campbell,
• Sriram Neelamegham,
• Frederick J. Krambeck,
• Kiyoko F. Aoki-Kinoshita and
• Nathan E. Lewis

Beilstein J. Org. Chem. 2020, 16, 2645–2662, doi:10.3762/bjoc.16.215

• position number inside the same brackets; ascending order from left to right. For some common modifications like N-acetylgalactosamine, instead of “A[2N],” Linear Code uses “AN” directly. Table 4 includes syntaxes of MS in Linear Code and common modified MSs. Common modification names can be found in Table

Comparative ligand structural analytics illustrated on variably glycosylated MUC1 antigen–antibody binding

• Christopher B. Barnett,
• Tharindu Senapathi and
• Kevin J. Naidoo

Beilstein J. Org. Chem. 2020, 16, 2540–2550, doi:10.3762/bjoc.16.206

• secondary structure, chain B is represented in cartoon and colored by secondary structure. The mucin peptide is represented as licorice. The Tn glycan (N-acetylgalactosamine) is represented as licorice, and the sugar ring is highlighted with the paper chain representation [18][19]. A comparison of root mean

A stereoselective and flexible synthesis to access both enantiomers of N-acetylgalactosamine and peracetylated N-acetylidosamine

• Bettina Riedl and
• Walther Schmid

Beilstein J. Org. Chem. 2018, 14, 856–860, doi:10.3762/bjoc.14.71

• Bettina Riedl Walther Schmid University of Vienna, Institute of Organic Chemistry, Währinger Straße 38, A-1090 Vienna, Austria 10.3762/bjoc.14.71 Abstract Synthetic approaches towards N-acetylgalactosamine (GalNAc) have been attracting considerable interest since this compound is known for its

• : asymmetric synthesis; carbohydrates; N-acetylgalactosamine; N-acetylidosamine; Introduction N-Acetylgalactosamine (GalNAc, Figure 1) and N-acetylidosamine (IdoNAc) belong to the group of 2-amino-2-deoxysugars, which can be found in a wide range of organisms as building blocks of, e.g., glycosaminoglycans

Stimuli-responsive oligonucleotides in prodrug-based approaches for gene silencing

• Françoise Debart,
• Christelle Dupouy and
• Jean-Jacques Vasseur

Beilstein J. Org. Chem. 2018, 14, 436–469, doi:10.3762/bjoc.14.32

• noncytotoxic fashion. Next, the authors prepared conjugates of the siRNNs via one A-SATE phosphotriester with a hepatocyte-specific tris-N-acetylgalactosamine targeting domain and demonstrated a stronger RNAi response in mouse liver (following subcutaneous or intravenous administration) than the same

Synthesis and NMR studies of malonyl-linked glycoconjugates of N-(2-aminoethyl)glycine. Building blocks for the construction of combinatorial glycopeptide libraries

• Markus Nörrlinger,
• Sven Hafner and
• Thomas Ziegler

Beilstein J. Org. Chem. 2016, 12, 1939–1948, doi:10.3762/bjoc.12.183

• -acetylglucosamine, d stands for N-acetylgalactosamine). Synthesis of building block 3. Synthesis of the dimeric glycoconjugate 4. Synthesis of building blocks 1a–d. Synthesis of building blocks 2a–d. ΔG‡c values of building blocks 1a,b. Supporting Information Supporting Information File 561: Experimental data

Exploring architectures displaying multimeric presentations of a trihydroxypiperidine iminosugar

• Camilla Matassini,
• Stefania Mirabella,
• Andrea Goti,
• Inmaculada Robina,
• Antonio J. Moreno-Vargas and
• Francesca Cardona

Beilstein J. Org. Chem. 2015, 11, 2631–2640, doi:10.3762/bjoc.11.282

• blank control, was found: this data is in complete agreement with the value obtained towards the commercial glycosidase. We finally evaluated 11·HCl against two lysosomal enzymes, N-acetylgalactosamine-6-sulfate sulfatase (GALNS) and iduronate 2-sulfatase that, being dimers [39], are in principle more

Multivalent scaffolds induce galectin-3 aggregation into nanoparticles

• Candace K. Goodman,
• Mark L. Wolfenden,
• Pratima Nangia-Makker,
• Anna K. Michel,
• Avraham Raz and
• Mary J. Cloninger

Beilstein J. Org. Chem. 2014, 10, 1570–1577, doi:10.3762/bjoc.10.162

• a series of carbohydrate-based ligands to galectin-3, which binds to lactose significantly better than to galactose or to N-acetylgalactosamine but does not bind to mannose [22][23][24]. Both the glycan ligand and the topological display on the cell surface are required for high affinity, selective

Chemo-enzymatic modification of poly-N-acetyllactosamine (LacNAc) oligomers and N,N-diacetyllactosamine (LacDiNAc) based on galactose oxidase treatment

• Christiane E. Kupper,
• Ruben R. Rosencrantz,
• Birgit Henßen,
• Helena Pelantová,
• Stephan Thönes,
• Anna Drozdová,
• Vladimir Křen and
• Lothar Elling

Beilstein J. Org. Chem. 2012, 8, 712–725, doi:10.3762/bjoc.8.80

• modification of terminal galactose and N-acetylgalactosamine residues of poly-N-acetyllactosamine (poly-LacNAc) oligomers and N,N-diacetyllactosamine (LacDiNAc) by galactose oxidase. Product formation starting from different poly-LacNAc oligomers was characterised and optimised regarding formation of the C6

Synthesis of glycosylated β³-homo-threonine conjugates for mucin-like glycopeptide antigen analogues

• Florian Karch and
• Anja Hoffmann-Röder

Beilstein J. Org. Chem. 2010, 6, No. 47, doi:10.3762/bjoc.6.47

• was available for this approach. Besides a recent report on α/δ-hybrid peptides derived from Neu2en and L-Glu [26], representing potentially immunogenic mimics of α-2,8-linked polysialic acid, only a few β-glycopeptides comprising N-acetylglucosamine [27][28][29] and N-acetylgalactosamine [30][31] (TN