70569-27-6Relevant academic research and scientific papers
Photooxidation of thiosaccharides mediated by sensitizers in aerobic and environmentally friendly conditions
Traverssi, Miqueas G.,Pe?é?ory, Alicia B.,Varela, Oscar,Colomer, Juan P.
, p. 9262 - 9273 (2021/03/16)
A series of β-d-glucopyranosyl derivates have been synthesized and evaluated in photooxidation reactions promoted by visible light and mediated by organic dyes under aerobic conditions. Among the different photocatalysts employed, tetra-O-acetyl riboflavin afforded chemoselectively the respective sulfoxides, without over-oxidation to sulfones, in good to excellent yields and short reaction times. This new methodology for the preparation of synthetically useful glycosyl sulfoxides constitutes a catalytic, efficient, economical, and environmentally friendly oxidation process not reported so far for carbohydrates.
One-Pot Relay Glycosylation
Cai, Lei,Fang, Jing,Li, Ting,Song, Zejin,Sun, Jiuchang,Wan, Qian,Xiao, Xiong,Zeng, Jing
supporting information, p. 5498 - 5503 (2020/04/09)
A novel one-pot relay glycosylation has been established. The protocol is characterized by the construction of two glycosidic bonds with only one equivalent of triflic anhydride. This method capitalizes on the in situ generated cyclic-thiosulfonium ion as the relay activator, which directly activates the newly formed thioglycoside in one pot. A wide range of substrates are well-accommodated to furnish both linear and branched oligosaccharides. The synthetic utility and advantage of this method have been demonstrated by rapid access to naturally occurring phenylethanoid glycoside kankanoside F and resin glycoside merremoside D.
Urea–hydrogen peroxide prompted the selective and controlled oxidation of thioglycosides into sulfoxides and sulfones
Singh, Adesh Kumar,Tiwari, Varsha,Mishra, Kunj Bihari,Gupta, Surabhi,Kandasamy, Jeyakumar
supporting information, p. 1139 - 1144 (2017/06/20)
A practical method for the selective and controlled oxidation of thioglycosides to corresponding glycosyl sulfoxides and sulfones is reported using urea–hydrogen peroxide (UHP). A wide range of glycosyl sulfoxides are selectively achieved using 1.5 equiv of UHP at 60 °C while corresponding sulfones are achieved using 2.5 equiv of UHP at 80 °C in acetic acid. Remarkably, oxidation susceptible olefin functional groups were found to be stable during the oxidation of sulfide.
Solid phase synthesis of glycopeptides using Shoda's activation of unprotected carbohydrates
Novoa, Alexandre,Barluenga, Sofia,Serba, Christelle,Winssinger, Nicolas
supporting information, p. 7608 - 7610 (2013/09/02)
An expedient and simple protocol to access S-linked glycopeptides by Fmoc SPPS using unprotected carbohydrates is reported. The utility of the method was demonstrated with the solid phase synthesis of a MUC1 fragment (20 mer) containing two glycosylation sites that were substituted with S-linked glycans. The Royal Society of Chemistry.
Towards dynamic drug design: Identification and optimization of β-galactosidase inhibitors from a dynamic hemithioacetal system
Caraballo, Remi,Sakulsombat, Morakot,Ramstroem, Olof
experimental part, p. 1600 - 1606 (2011/05/06)
A discovery strategy relying on the identification of fragments through resolution of a constitutional dynamic system, coupled to subsequent static ligand design and optimization, is demonstrated. The strategic design and synthesis of the best molecular fragments identified from a dynamic hemithioacetal system into static ligand structures yielded a range of β-galactosidase inhibitors. Two series of structures mimicking the hemithioacetal motif were envisaged: thioglycosides and C-glycosides. Inhibition studies provided important structural information for the two groups, and 1-thiobenzyl-b-d-galactopyranoside demonstrated the best inhibitory effects.
Green glycosylation using ionic liquid to prepare alkyl glycosides for studying carbohydrate-protein interactions by SPR
Javier Munoz,Andre, Sabine,Gabius, Hans-Joachin,Sinisterra, Jose V.,Hernaiz, Maria J.,Linhardt, Robert J.
experimental part, p. 373 - 379 (2010/04/22)
Several simple glycosides of d-glucose (Glc) and N-acetyl-d-galactosamine (GalNAc) were prepared in a single step glycosylation reaction using unprotected and unactivated sugar donors. The resulting GalNAc glycoside, containing a bifunctional linker, was used to immobilize this glycoconjugate to a self assembled monolayer on a gold biosensor chip. Surface plasmon resonance (SPR) experiments demonstrated that this immobilized glycoconjugate bound to GalNAc specific lectin, Viscum album agglutinin.
Probing the aglycon promiscuity of an engineered glycosyltransferase
Gantt, Richard W.,Goff, Randal D.,Williams, Gavin J.,Thorson, Jon S.
supporting information; experimental part, p. 8889 - 8892 (2009/05/26)
(Figure Presented) A sweet library: Two variants (wild-type (WT) and a triple mutant) of glycosyltransferase (GT) OleD have been shown to catalyze glycosylation of over 70 substrates, formation of O-, S- and N-glycosidic bonds, and iterative glycosylation (see scheme). Identified substrates include nucleophiles not previously known to act in GT reactions and span numerous natural product and therapeutic drug classes.
Synthesis of both possible isomers of the northwest quadrant of Altromycin B
Pasetto, Paolo,Franck, Richard W.
, p. 8042 - 8060 (2007/10/03)
The synthesis of the northwest quadrant of Altromycin B is described. The preparation of the two epimers at the quaternary carbon of the 6-deoxy-C-altrose moiety in the northwest quadrant is accomplished starting from D-glucose. A key step of our synthetic sequence is the formation of the C-glycoside linkage via the Ramberg-Baecklund reaction. Two different routes are explored, which differ mainly on the timing of the conversion of glucose to altrose, either before or after the preparation of the C-glycoside. The conformation behavior of variously substituted C-altropyranoside rings is also discussed.
