RT Journal Article
T1 Glycosyl Aldehydes: New Scaffolds for the Synthesis of Neoglycoconjugates via Bioorthogonal Oxime Bond Formation
A1 Reina, José J.
A1 Rioboo Vidal, Alicia
A1 Montenegro García, Javier
K1 Neoglycoconjugates
K1 Glycosyl aldehydes
K1 Oxime bond formation
K1 Carbohydrates
K1 Bioorthogonal chemistry
K1 Chemoselective ligation
AB The straightforward preparation of glycosyl neoconjugates by oxime (or hydrazone) bond formation represents a key bioorthogonal tool in chemical biology. However, when this strategy is employed by reacting the reducing end of the glycan moiety, the configuration and the stereochemical information is lost due to partial (or complete) opening of the glycan cyclic hemiacetal and the formation of the corresponding opened tautomers. We have completed the synthesis of a library of glycosyl aldehydes to be used as scaffold for the synthesis of neoglycoconjugates via oxime bond formation. These glycosyl aldehydes constitute a simple and accessible alternative to avoid loss of chiral information when conjugating, by oxime (or hydrazone) bonds, the aldehyde functionality present at the reducing end of natural carbohydrates
PB Georg Thieme Verlag
SN 0039-7881
YR 2018
FD 2018-01-02
LK http://hdl.handle.net/10347/16497
UL http://hdl.handle.net/10347/16497
LA eng
NO Montenegro, J., Reina, J., & Rioboo, A. (2018). Glycosyl Aldehydes: New Scaffolds for the Synthesis of Neoglycoconjugates via Bioorthogonal Oxime Bond Formation. Synthesis, 50(04), 831-845. http://dx.doi.org/10.1055/s-0036-1591082
NO This work was partially supported by the Spanish Agencia Estatal de Investigación (AEI) [CTQ2014–59646-R], the Xunta de Galicia (ED431G/09, ED431C 2017/25 and 2016-AD031) and the ERDF. J.M. received a Ramón y Cajal (RYC-2013–13784), an ERC-Stg (DYNAP- 677786) and a Young Investigator Grant from the Human Frontier Science Research Program (RGY0066/2017)
DS Minerva
RD 24 abr 2026