Synthesis of Uronic Acid Containing Oligosaccharides

Li, Sizhe; Wang, Zhen; Marel, Gijsbert A. van der; Codée, Jeroen D. C.

doi:10.1016/b978-0-12-819475-1.00072-9

“…3 In subsequent studies with Codée, the construction of the analogous oligomer containing L-GulA 4 and a mixed sequence fragment 5 were both achieved. Excellent reviews of alginate synthesis are provided by Clausen, 6 Cai 7 and Codée; 8 all precede the very recent advance of Yang 9 who has https://doi.org/10.26434/chemrxiv-2024-sns6w ORCID: https://orcid.org/0000-0003-3306-2550 Content not peer-reviewed by ChemRxiv. License: CC BY-NC-ND 4.0 Scheme 1.…”

Section: Introductionmentioning

confidence: 99%

Synthetic Access to L-Guluronic Acid via Fluorine-Directed C-5 Epimerization

See,

Wimmer,

Zhang

et al. 2024

Preprint

2

0

View full text Add to dashboard Cite

L-Guluronic acid is integral to the structures of alginates and to the pathogenesis of Pseudomonas aeruginosa. The exploitation of this hexose in both existing and new contexts is, however, limited by its prohibitively high commercial cost. We report on a short and efficient synthetic route to an L-GulA building block from a simple D-mannose thioglycoside. In this synthesis, the fluorine-directing effect is exploited to achieve a stereoselective C-5 epimerization. DFT calculations illuminate the substituent effects which operate to confer this selectivity.

show abstract

An efficient and direct esterification of uronic acids using H2SO4-SiO2 at room temperature

Tiwari

¹

,

Murugan²,

Sabiah

³

et al. 2022

Tetrahedron Letters

View full text Add to dashboard Cite

Synthetic Access to l-Guluronic Acid via Fluorine-Directed C-5 Epimerization

See,

Wimmer,

Zhang

et al. 2024

J. Org. Chem.

0

View full text Add to dashboard Cite

L-Guluronic acid is integral to the structures of alginates and to the pathogenesis of Pseudomonas aeruginosa. The exploitation of this hexose in both existing and new contexts is, however, limited by its prohibitively high commercial cost. We report on a short and efficient synthetic route to an L-GulA building block from a simple D-mannose thioglycoside. In this synthesis, the fluorine-directing effect is exploited to achieve a stereoselective C-5 epimerization. DFT calculations illuminate the substituent effects, which operate to confer this selectivity.

show abstract

Synthesis of Uronic Acid Containing Oligosaccharides

Cited by 3 publications

References 124 publications

Synthetic Access to L-Guluronic Acid via Fluorine-Directed C-5 Epimerization

Synthetic Access to L-Guluronic Acid via Fluorine-Directed C-5 Epimerization

An efficient and direct esterification of uronic acids using H2SO4-SiO2 at room temperature

Synthetic Access to l-Guluronic Acid via Fluorine-Directed C-5 Epimerization

Contact Info

Product

Resources

About