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

• -acetylglucosaminyltransferase I (GnT-I) reaction transition state [11]. Previously, we have designed 2-thiohexofuranoside skeletons bearing a phosphate group in position 1 by molecular modeling as potential transition state inhibitors of human glycosyltransferase I (GnT-I) [12], the bisubstrate enzyme requiring a metal co

Synthesis of C-glycosyl phosphonate derivatives of 4-amino-4-deoxy-α-ʟ-arabinose

• Lukáš Kerner and
• Paul Kosma

Beilstein J. Org. Chem. 2020, 16, 9–14, doi:10.3762/bjoc.16.2

• in more detail using phosphodiester-linked derivatives in both anomeric configurations and containing short lipid appendages in order to define the minimum structural requirements for Ara4N glycosyltransferase substrates [9]. In parallel, we have started to develop C-phosphonate analogues as these

Electron-deficient pyridinium salts/thiourea cooperative catalyzed O-glycosylation via activation of O-glycosyl trichloroacetimidate donors

• Mukta Shaw,
• Yogesh Kumar,
• Rima Thakur and
• Amit Kumar

Beilstein J. Org. Chem. 2017, 13, 2385–2395, doi:10.3762/bjoc.13.236

• acceleration of many important biochemical reactions, such as glycosyltransferase reactions, hydrolysis of strong amide bonds and others [11][12][13]. Taking inspiration from nature, in the last few decades chemists around the world have utilized organic molecules to accelerate many imperative organic

Enzymatic synthesis of glycosides: from natural O- and N-glycosides to rare C- and S-glycosides

• Jihen Ati,
• Pierre Lafite and
• Richard Daniellou

Beilstein J. Org. Chem. 2017, 13, 1857–1865, doi:10.3762/bjoc.13.180

• of rare or unnatural glycosidic linkages. Keywords: enzyme; glycochemistry; glycoside hydrolase; glycosyltransferase; mechanism; Introduction The role of glycoconjugates is of prime importance, as they are nowadays well known to mediate many biological processes [1]. As a consequence, in a recently

Glycoscience@Synchrotron: Synchrotron radiation applied to structural glycoscience

• Serge Pérez and
• Daniele de Sanctis

Beilstein J. Org. Chem. 2017, 13, 1145–1167, doi:10.3762/bjoc.13.114

• , including a fucosyltransferase, FUT1 that belongs to the glycosyltransferase family 37. The determination of the crystal structure revealed yet another variant of a GT-B fold and could explain FUT1 substrate specificity (Figure 9). Furthermore, the determination in complex with a minimal xyloglucan

Urea–hydrogen peroxide prompted the selective and controlled oxidation of thioglycosides into sulfoxides and sulfones

• Adesh Kumar Singh,
• Varsha Tiwari,
• Kunj Bihari Mishra,
• Surabhi Gupta and
• Jeyakumar Kandasamy

Beilstein J. Org. Chem. 2017, 13, 1139–1144, doi:10.3762/bjoc.13.113

• , glycosyl sulfones are known to be potential glycosyltransferase inhibitors [13]. Glycosyl sulfoxides and sulfones are prepared from the corresponding sulfides using various oxidizing reagents [5][6][7][10]. Although a number of oxidation methods were developed for the oxidation of simple organic sulfides

Silyl-protective groups influencing the reactivity and selectivity in glycosylations

• Mikael Bols and
• Christian Marcus Pedersen

Beilstein J. Org. Chem. 2017, 13, 93–105, doi:10.3762/bjoc.13.12

• to be highly α-selective (Table 1) presumably due to steric hindrance from the 2-O-TBS on the β-face. This donor was recently used in the synthesis of glycosyltransferase acceptor substrates [53]. Yet the 2-O-TBS protection does not always have this effect. In a recent paper it was shown that in a

Muraymycin nucleoside-peptide antibiotics: uridine-derived natural products as lead structures for the development of novel antibacterial agents

• Daniel Wiegmann,
• Stefan Koppermann,
• Marius Wirth,
• Giuliana Niro,
• Kristin Leyerer and
• Christian Ducho

Beilstein J. Org. Chem. 2016, 12, 769–795, doi:10.3762/bjoc.12.77

• been reported elsewhere [52]. The membrane-associated steps commence with the transfer of UDP-MurNAc-pentapeptide to the lipid carrier undecaprenyl phosphate, catalysed by translocase I (MraY), to give lipid I (Figure 4, product of step B). The glycosyltransferase MurG attaches a GlcNAc sugar to

• donor 117, catalysed by glycosyltransferase LipN, furnishes the complete nucleoside core structure 118 (Scheme 11). The order of 6'-N-(3-aminopropyl) attachment and 5'-O-aminoribosylation is not fully clear yet, i.e., it is not elucidated if 101 or 6'-N-aminoalkyl intermediate 103 (see Scheme 10) act as

Synthesis and biological evaluation of a novel MUC1 glycopeptide conjugate vaccine candidate comprising a 4’-deoxy-4’-fluoro-Thomsen–Friedenreich epitope

• Manuel Johannes,
• Maximilian Reindl,
• Bastian Gerlitzki,
• Edgar Schmitt and
• Anja Hoffmann-Röder

Beilstein J. Org. Chem. 2015, 11, 155–161, doi:10.3762/bjoc.11.15

• changes in glycosyltransferase activity and expression [8][9][10]. Furthermore, the prevalence of truncated saccharide antigens such as the Tn antigen [11], the Thomsen–Friedenreich (TF) antigen, and their sialylated congeners [8][9][10][12] leads to an insufficient shielding of the peptide backbone

Carbohydrate PEGylation, an approach to improve pharmacological potency

• M. Eugenia Giorgi,
• Rosalía Agusti and
• Rosa M. de Lederkremer

Beilstein J. Org. Chem. 2014, 10, 1433–1444, doi:10.3762/bjoc.10.147

• steric effects [31]. The strategy is based on the finding that certain PEGylated nucleotide-sugars are effectively transferred to a glycan acceptor by the corresponding glycosyltransferase. A modified sialic acid PEGylated at the 5’-amino position in the CMP nucleotide (CMP-SA-5-NHCOCH2NHPEG) can be

The use of glycoinformatics in glycochemistry

• Thomas Lütteke

Beilstein J. Org. Chem. 2012, 8, 915–929, doi:10.3762/bjoc.8.104

• accessible to other researchers, they can be used in new projects to actually improve the existing status, rather than the wheel having to be reinvented every time by starting from scratch and redeveloping basic concepts and sources. Carbohydrate structure databases. Glycosyltransferase/glycan-binding

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

• oligomers containing terminally and/or internally modified galactose residues were obtained, which can be used for binding studies and various other applications. Keywords: chemo-enzymatic synthesis; galactose oxidase; glycosyltransferase; LacDiNAc; poly-N-acetyllactosamine; Introduction N

• LacNAc (7a) is not accepted by either glycosyltransferase. Reaction scheme of terminal galactose in poly-LacNAc-glycans (1a–d) or GalNAc in LacDiNAc (2) by galactose oxidase, to the corresponding 6-aldehyde (3a–d, 4). Subsequent further oxidation yields the corresponding galacturonic acids (5a–d, 6), and

Study of thioglycosylation in ionic liquids

• Jianguo Zhang and
• Arthur Ragauskas

Beilstein J. Org. Chem. 2006, 2, No. 12, doi:10.1186/1860-5397-2-12

• -acetyl-glycoside derivatives have been used in the synthesis of glycosyltransferase inhibitors and clearing agents to enhance anti-tumor activities.[10][11] In addition, alkyl glycosides possessing long alkyl chain have gained wide interest as non-ionic surfactants.[12] A variety of reagents have been