Optimizations of lipid II synthesis: an essential glycolipid precursor in bacterial cell wall synthesis and a validated antibiotic target

• Milandip Karak,
• Cian R. Cloonan,
• Brad R. Baker,
• Rachel V. K. Cochrane and
• Stephen A. Cochrane

Beilstein J. Org. Chem. 2024, 20, 220–227, doi:10.3762/bjoc.20.22

• analogues through the incorporation of alternative building blocks at different stages of synthesis. Keywords: chemical glycosylation; lipid II; peptidoglycan; polyprenyls; total synthesis; Introduction Lipid II (Figure 1) is an essential bacterial glycolipid involved in peptidoglycan biosynthesis [1]. It

Comparison of glycosyl donors: a supramer approach

• Anna V. Orlova,
• Nelly N. Malysheva,
• Maria V. Panova,
• Nikita M. Podvalnyy,
• Michael G. Medvedev and
• Leonid O. Kononov

Beilstein J. Org. Chem. 2024, 20, 181–192, doi:10.3762/bjoc.20.18

• , Russian Federation 10.3762/bjoc.20.18 Abstract The development of new methods for chemical glycosylation commonly includes comparison of various glycosyl donors. An attempted comparison of chemical properties of two sialic acid-based thioglycoside glycosyl donors, differing only in the substituent at O-9

• spectrum of phenomena including virus and bacterial recognition and cellular adhesion [1][2][3][4][5][6][7][8][9][10][11]. The development of effective means for the preparation of α-sialosides through chemical glycosylation (sialylation) received considerable attention since sialo-containing saccharides

Synthesis of protected precursors of chitin oligosaccharides by electrochemical polyglycosylation of thioglycosides

• Md Azadur Rahman,
• Kana Kuroda,
• Hirofumi Endo,
• Norihiko Sasaki,
• Tomoaki Hamada,
• Hiraku Sakai and
• Toshiki Nokami

Beilstein J. Org. Chem. 2022, 18, 1133–1139, doi:10.3762/bjoc.18.117

• from natural sources or by synthesis via chemical glycosylation [2]. Total syntheses of chitin and chitosan oligosaccharides based on conventional chemical glycosylation of protected monosaccharides as building blocks have already been reported. Convergent synthesis using oligosaccharide building

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

• ). No enzyme has been reported for the synthesis of α-mannosides. Similarly, polymerization approaches remain to date underrepresented. α-Mannosides can be reliably prepared through chemical glycosylation, which is in general highly α-stereoselective. Construction of the 1,2-trans linkage of α

Synthetic and semi-synthetic approaches to unprotected N-glycan oxazolines

• Antony J. Fairbanks

Beilstein J. Org. Chem. 2018, 14, 416–429, doi:10.3762/bjoc.14.30

• selective chemical glycosylation or protection of the primary OH groups; the remaining secondary hydroxy group of the products of the latter process could also be glycosylated. Ultimately this methodology allows the synthesis of the considerably more complex N-glycans, for example tri- (and presumably in

Intramolecular glycosylation

• Xiao G. Jia and
• Alexei V. Demchenko

Beilstein J. Org. Chem. 2017, 13, 2028–2048, doi:10.3762/bjoc.13.201

• very first experiments performed by Arthur Michael and Emil Fischer in the late 1800’s, the glycosylation reaction remains challenging to chemists. Enzymatic glycosylation reactions are highly stereoselective [33]. However, the stereocontrol of chemical glycosylation reactions remains cumbersome

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

• thought to represent powerful and greener alternatives to conventional chemical glycosylation procedures. The knowledge of their corresponding mechanisms has already allowed the development of efficient biocatalysed syntheses of complex O-glycosides. These enzymes can also now be applied to the formation

2-Allylphenyl glycosides as complementary building blocks for oligosaccharide and glycoconjugate synthesis

• Hemali D. Premathilake and
• Alexei V. Demchenko

Beilstein J. Org. Chem. 2012, 8, 597–605, doi:10.3762/bjoc.8.66

• activated for chemical glycosylation under a variety of conditions, through both direct and remote pathways. Differentiation between the two activation pathways was achieved in a mechanistic study. The orthogonal-type activation of the AP moiety along with common thioglycosides allows for the execution of

• , perbenzoylated 1b, and derivative 1c equipped with the superarming protecting-group pattern (2-O-benzoyl-3,4,6-tri-O-benzyl) [31]. For comparison, we also obtained the AP donor 1d of the D-galacto series. With glycosyl donors 1a–d in hand, we began evaluating their applicability to chemical glycosylation using a

• activated for chemical glycosylation under a variety of conditions including Lewis acid and iodonium ion mediated pathways. The two activation pathways were confirmed by a mechanistic study. We also demonstrated that the application of the AP moiety allows executing oligosaccharide assembly by an orthogonal

Preparation of aminoethyl glycosides for glycoconjugation

• Robert Šardzík,
• Gavin T. Noble,
• Martin J. Weissenborn,
• Andrew Martin,
• Simon J. Webb and
• Sabine L. Flitsch

Beilstein J. Org. Chem. 2010, 6, 699–703, doi:10.3762/bjoc.6.81

• more successful and produced mainly the beta anomer 17. Maltoside 18 was generated by the same microwave-mediated glycosylation as developed for lactoside 16 (Method B) and in reasonable yield. N-Acetyl neuraminic acid (sialic acid) is an important component of cell surfaces and chemical glycosylation