Synthesis of galactofuranosyl-(1 → 5)-thiodisaccharide glycomimetics as inhibitors of a β-<scp>d</scp>-galactofuranosidase

Fiego, Marcos J. Lo; Marino, Carla; Varela, Oscar

doi:10.1039/c5ra06899a

Cited by 8 publications

(7 citation statements)

References 52 publications

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“…To improve the water solubility of the complexes, we carried out a study of the deprotection of the carbohydrate unit. We started with 5a as a model complex under three different deprotection conditions at room temperature: (i) Et 3 N/H 2 O/MeOH, 30 min; 30 (ii) NaOMe/MeOH/CH 2 Cl 2, 1 h; 31 and (iii) K 2 CO 3 /MeOH/CH 2 Cl 2 , 1 h. 32 All attempts to deprotection led to a decomposition of the complex, obtaining a mixture of the corresponding deprotected complex ( 7a ) and the bis-carbene complex ( 8a ), determined by the signal pattern of the imidazole portion and the presence of two anomeric signals in the NMR spectra in D 2 O. The deprotection condition (iii) allowed obtaining complex 7a as the majority species ( Figure 2 ).…”

Section: Resultsmentioning

confidence: 99%

Galactopyranoside-SubstitutedN-Heterocyclic Carbene Gold(I) Complexes: Synthesis, Stability, and Catalytic Applications to Alkyne Hydration

et al. 2022

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A series of novel gold(I) complexes bearing galactopyranoside-based N -heterocyclic carbene ligands have been synthesized via transmetalation of the corresponding Ag(I) complex. Gold(I) complexes have been characterized by NMR, Fourier transform infrared (FTIR), and elemental analysis. An exhaustive NMR analysis shows that the complexes are not stable when hydroxyl groups are deprotected. Catalytic studies, using the alkyne hydration as a model reaction, indicate that the synthesized complexes are active and reusable.

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Section: Resultsmentioning

confidence: 99%

Galactopyranoside-SubstitutedN-Heterocyclic Carbene Gold(I) Complexes: Synthesis, Stability, and Catalytic Applications to Alkyne Hydration

et al. 2022

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“…In particular those derived from carbohydrates have been widely applied to the synthesis of oligosaccharides and other glycomimetics. [7a], [34d], …”

Section: Resultsmentioning

confidence: 99%

A Domino Epoxide Ring‐Opening Xanthate Migration Reaction: An Alternative Entry to Thiosugars

et al. 2018

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A sterereospecific and efficient synthesis of thiosugars derived from levoglucosenone and methyl α‐d‐glucopyranoside was developed by a domino epoxide ring opening‐ xanthate migration to afford 1,3‐oxathiolane‐2‐thiones in high yields. The stereochemical outcome of the new C–S bond was defined by the configuration of the starting materials. The 1,3‐oxathiolane‐2‐thiones were subsequently submitted to a second tandem reaction affording the corresponding 2,3‐episulfide alcohols. The thiosugars obtained are useful building blocks for the synthesis of thiooligosaccharides with potential biological properties.

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“…Many of the resulting thiodisaccharides proved to be interesting enzyme inhibitors. [104,107,[111][112][113][114] Moreover, promising anti-cancer activities were also described for some of them. [28][29][30] In 1995, Witczak described the synthesis of two α(1!4) thiodisaccharides via Michael addition, one of them bearing a GlcNAc moiety.…”

Section: Michael and Michael-type Addition Reactionsmentioning

confidence: 99%

“…They explored the reactivity of α,β‐unsaturated derivatives, mainly the popular levoglucosenone and dihydropyran‐2‐ones as substrates, and thioaldoses as nucleophiles. Many of the resulting thiodisaccharides proved to be interesting enzyme inhibitors [104,107,111–114] . Moreover, promising anti‐cancer activities were also described for some of them [28–30] …”

Section: General Strategies For the Access To Thiodisaccharides: The Hexnac Challengementioning

confidence: 99%

Synthesis of Thiodisaccharides Bearing N‐Acetylhexosamine Residues: Challenges, Achievements and Perspectives

Cristófalo

Cano

Uhrig

2021

The Chemical Record

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Carbohydrate-protein interactions are involved in a myriad of biological processes. Thus, glycomimetics have arisen as one of the most promising synthetic targets to that end. Within the broad variety of glycomimetics, thiodisaccharides have proven to be excellent tools to study these processes, and even more, some of them unveiled interesting biological activities. This review brings together research made on the introduction of N-acetylhexosamine residues into thiodisaccharides to date, passing through classic substitution (as S N 2, thioglycosylation and ring-opening reactions) and addition (as thiol-ene coupling and Michael-type additions) reactions. Recent and interesting developments regarding addition reactions to vinyl azides, cross-coupling reactions and novel chemoenzymatic methods are also discussed.

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Synthesis of galactofuranosyl-(1 → 5)-thiodisaccharide glycomimetics as inhibitors of a β-d-galactofuranosidase

Abstract: Description of the synthesis, molecular modeling and inhibitory properties of furanosyl thiodisaccharides that are mimetics of the motif β-d-Galf-(1 → 5)-d-Galf, found in glycoconjugates of pathogenic microorganisms.

Cited by 8 publications

References 52 publications

Galactopyranoside-SubstitutedN-Heterocyclic Carbene Gold(I) Complexes: Synthesis, Stability, and Catalytic Applications to Alkyne Hydration

Galactopyranoside-SubstitutedN-Heterocyclic Carbene Gold(I) Complexes: Synthesis, Stability, and Catalytic Applications to Alkyne Hydration

A Domino Epoxide Ring‐Opening Xanthate Migration Reaction: An Alternative Entry to Thiosugars

Synthesis of Thiodisaccharides Bearing N‐Acetylhexosamine Residues: Challenges, Achievements and Perspectives

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