Progress and challenges in the synthesis of sequence controlled polysaccharides

• Giulio Fittolani,
• Theodore Tyrikos-Ergas,
• Denisa Vargová,
• Manishkumar A. Chaube and
• Martina Delbianco

Beilstein J. Org. Chem. 2021, 17, 1981–2025, doi:10.3762/bjoc.17.129

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

• ). Similarly, galactofuranose, a common fungal monosaccharide, would be written “A^” Open form rule indicates that if the MS at the reducing end is open – a linear rather than cyclic MS, then the final character to the right of the string should be "o". For example, lactose, galactose β-linked to glucose would

Synthesis, docking study and biological evaluation of ᴅ-fructofuranosyl and ᴅ-tagatofuranosyl sulfones as potential inhibitors of the mycobacterial galactan synthesis targeting the galactofuranosyltransferase GlfT2

• Marek Baráth,
• Jana Jakubčinová,
• Zuzana Konyariková,
• Stanislav Kozmon,
• Katarína Mikušová and
• Maroš Bella

Beilstein J. Org. Chem. 2020, 16, 1853–1862, doi:10.3762/bjoc.16.152

• galactofuranose (Galf) residues linked by alternating β-(1→5)- and β-(1→6)-glycosidic bonds [4]. The Galf monomer is restricted to some bacteria, fungi and a few protozoan species, and it seems to be absent in humans [5]. The enzymes participating in the galactan build-up could thus be considered as potential

Chemical synthesis of the pentasaccharide repeating unit of the O-specific polysaccharide from Escherichia coli O132 in the form of its 2-aminoethyl glycoside

• Debasish Pal and
• Balaram Mukhopadhyay

Beilstein J. Org. Chem. 2019, 15, 2563–2568, doi:10.3762/bjoc.15.249

• glycoside; diarrhea; galactofuranose; O-specific polysaccharide; total synthesis; Introduction O-Polysaccharides are the most complex molecular systems present in the bacterial cell wall owing to the presence of various sugar residues connected through diverse glycosidic linkages. These complex structures

Preactivation-based chemoselective glycosylations: A powerful strategy for oligosaccharide assembly

• Weizhun Yang,
• Bo Yang,
• Sherif Ramadan and
• Xuefei Huang

Beilstein J. Org. Chem. 2017, 13, 2094–2114, doi:10.3762/bjoc.13.207

• % vs 30%) without the need for large excess (5–10 equiv) of building blocks. Recently, using a series of highly efficient preactivation-based glycosylation reactions, Ye and co-workers synthesized a mycobacterial arabinogalactan [62], which is composed of 30 D-galactofuranose residues (Galf30) linked

Glyco-gold nanoparticles: synthesis and applications

• Federica Compostella,
• Olimpia Pitirollo,
• Alessandro Silvestri and
• Laura Polito

Beilstein J. Org. Chem. 2017, 13, 1008–1021, doi:10.3762/bjoc.13.100

• -glycans, such as those found on the HIV gp120 protein, and Lewis-type glycans. Ligand recognition often initiates events which are able to trigger specific signaling and result in a robust immune activation in humans. For example, galactofuranose (Galf) functionalized AuNPs were found able to elicit a pro

Expedient synthesis of 1,6-anhydro-α-D-galactofuranose, a useful intermediate for glycobiological tools

• Luciana Baldoni and
• Carla Marino

Beilstein J. Org. Chem. 2014, 10, 1651–1656, doi:10.3762/bjoc.10.172

• three-step procedure for the synthesis of 1,6-anhydro-α-D-galactofuranose is described. The key step involves the formation of the galactofuranosyl iodide by treatment of per-O-TBS-D-Galf with TMSI, the selective 6-O-desilylation by an excess of TMSI, and the simultaneous nucleophilic attack of the 6

• -hydroxy group on the anomeric carbon, with the iodide as a good leaving group. This compound is a good precursor for building blocks for the construction of 1→6 linkages. Keywords: 1,6-anhydro-α-D-Galf; galactofuranosyl iodide; galactofuranosyl precursor; per-tert-butyldimethylsilyl-β-D-galactofuranose

• starts from a galactofuranose (D-Galf) template conveniently derivatized. Pioneer procedures for the synthesis of 2 involved the pyrolysis of D-Gal under reduced pressure [11][12] and the acid treatment under heating [13], with the subsequent tedious separation from several byproducts, including the

Straightforward synthesis of a tetrasaccharide repeating unit corresponding to the O-antigen of Escherichia coli O16

• Manas Jana and
• Anup Kumar Misra

Beilstein J. Org. Chem. 2013, 9, 1757–1762, doi:10.3762/bjoc.9.203

• containing D-glucosamine, L-rhamnose, D-glucose and D-galactofuranose moieties in a 1:1:1:1 ratio (Figure 1). The emergence of multi drug resistant bacterial strains forces medicinal chemists to develop new approaches to combat bacterial infections. Since the structure of the O-antigen influences the

Synthesis of a derivative of α-D-Glcp(1->2)-D-Galf suitable for further glycosylation and of α-D-Glcp(1->2)-D-Gal, a disaccharide fragment obtained from varianose

• Carla Marino,
• Carlos Lima,
• Karina Mariño and
• Rosa M. de Lederkremer

Beilstein J. Org. Chem. 2012, 8, 2142–2148, doi:10.3762/bjoc.8.241

• monitor the natural disaccharide released from varianose by mild acid degradation. The synthesis, performed by the glycosylaldonolactone approach, involved a glucosylgalactofuranose derivative, suitable for the synthesis of higher oligosaccharides with an internal D-Galf. Keywords: α-D-galactofuranose

• contains galactofuranose (Galf) in both α and β-configurations in the repeating unit (Figure 1). Further studies established that the galactofuran of alternating β(1→6) and β(1→5)Galf units is branched at the O-2 of the (1→5)-linked Galf with the disaccharide α-D-Glcp(1→2)-α-D-Galf [4]. Mild acid

• -2, C-3), 73.3 (CH2Ph), 72.4 (CH2Ph), 71.1 (C-5’), 69.8 (C-5), 67.8 (C-6’), 62.2 (C-6); Anal. calcd for C61H56O14: C, 72.32; H, 5.57; found: C, 72.39; H, 5.65. 2-O-(2,3,4,6-Tetra-O-benzyl-α-D-glucopyranosyl)-3,5,6-tri-O-benzoyl-α,β-D-galactofuranose (8): To a solution of bis(2-butyl-3-methyl)borane

Carbasugar analogues of galactofuranosides: α-O-linked derivatives

• Jens Frigell and
• Ian Cumpstey

Beilstein J. Org. Chem. 2010, 6, 1127–1131, doi:10.3762/bjoc.6.129

• exemplify the method. Keywords: carbasugars; etherification; galactofuranose; glycomimetics; pseudodisaccharides; regioselective; Introduction Galactofuranose is found in nature as a component of glycoconjugates in many microorganisms [1][2]. Galactofuranosides with the α configuration are rather less

• -galactofuranose, which has an α configuration [1][2]. Modified, hydrolytically stable analogues of galactofuranosides could find application in the design and synthesis of potential inhibitors of the enzymes involved in the biosynthesis of galactofuranose-containing glycoconjugates. We have recently developed

• configuration) followed by intramolecular displacement of the C2 tosylate (with inversion of configuration). We synthesised the same epoxide 4 (78%) by treatment of isolated 3,5,6-tri-O-benzyl-2-O-(toluene-4-sulfonyl)-4a-carba-β-D-galactofuranose [9] with sodium hydride in DMF. We investigated ring-opening of