Synthesis of propyl and 2-aminoethyl glycosides of α-d-galactosyl-(1→3′)-β-lactoside

Yudina, O. N.; Sherman, Andrei A.; Nifantiev, Nikolay E.

doi:10.1016/s0008-6215(01)00097-0

Cited by 26 publications

(11 citation statements)

References 21 publications

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“…A unique 1 H-NMR peak was observed as a doublet at δ 5.15−5.18 ppm (in D 2 O solvent), which corresponds to the proton at the 1-position of an α(1,3)-linked galactose. 27 Reduction of azido compounds 15 − 17 to their corresponding primary amines followed by squarate coupling gave the target epitopes 1 − 3 in 39−66% yield.…”

Section: Resultsmentioning

confidence: 99%

The design and synthesis of an α-Gal trisaccharide epitope that provides a highly specific anti-Gal immune response

et al. 2017

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Carbohydrate antigens displaying Galα(1,3)Gal epitopes are recognized by naturally occurring antibodies in humans. These anti-Gal antibodies comprise up to 1% of serum IgG and has been viewed as detrimental as they are responsible for hyperacute organ rejections. In order to model this condition, α(1,3)galactosyltransferase-knockout mice are innoculated agaisnt the Galα(1,3)Gal epitope. In our study, two α-Gal trisaccharide epitopes composed of either Galα(1,3)Galβ(1,4)GlcNAc or Galα(1,3)Galβ(1,4)Glc linked to a squaric acid ester moiety were examined for their ability to elicit immune response in KO mice. Both target epitopes were synthesized using a two-component enzymatic system using modified dissacharide substrates containing a linker moiety for coupling. While both glycoconjugate vaccines induced the required high anti-Gal IgG antibody titers, it was found that this response had exquisite specificity for the Galα(1,3)Galβ(1,4)GlcNAc hapten used, with little cross reactivity with the Galα(1,3)Galβ(1,4)Glc hapten. Our findings indicate that while homogenous glycoconjugate vaccines provide high IgG titers, the carrier and adjuvanting factors can deviate the specificty to an antigenic determinant outside the purview of interest.

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Section: Resultsmentioning

confidence: 99%

The design and synthesis of an α-Gal trisaccharide epitope that provides a highly specific anti-Gal immune response

et al. 2017

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“…Classical transformation of an alcoholic hydroxyl group into a better leaving group, such as tosylate, mesylate, or incorporation of iodide instead a hydroxyl group, provide the opportunity to obtain the desired products. 14,[26][27][28][29][30][31][32][33][34][35][36] In our recent studies, we focused on the long chain compounds which possess a fluorinated alkyl chain and a different -CH2-linkers attached directly to the azido group. Although the preparation of azides is very well documented, there are no much precedences to synthesize fluorinated analogues.…”

Section: Resultsmentioning

confidence: 99%

“…Typically, transformation of a tosylate or mesylate into the corresponding fluoroalkyl azide proceeds in toluene or DMSO as solvent, sometimes with addition of a catalyst such as 18-crown-6 ether. 31,37,47,48 Other reports use DMF/benzene as a solvent and simple nucleophilic substitution with sodium azide at elevated temperature. 14 We have changed the solvent to hexamethylphosphoramide (HMPA) and used a threefold excess of sodium azide without any extra additives.…”

Section: Resultsmentioning

confidence: 99%

Fluorinated organic azides – their preparation and synthetic application

Tomaszewska¹,

Koroniak-Szejn²,

Koroniak³

2016

Arkivoc

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Alkyl azides are widely used in many reactions. Although synthesis of such species is relatively well documented, fluorinated azides, especially with large perfluorinated or highly fluorinated groups, are sometimes tricky to make. The presence of fluorine in reacting molecules, sometimes causes significant changes in the reactivity of reacting species. In this paper we give a short overview of re-examination of currently available methods of synthesis of selected azides with highly fluorinated groups.

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“…Disaccharide donor 25 was synthesized by coupling the monosaccharide 24 with trichloroacetimidate donor 9 in the presence of TMSOTf with 77% yield. Glycosylation of 25 with a disaccharide acceptor 26 [39] using NIS TfOH as the promoters produced tetrasaccharide 27 (64%). Global deprotection leaded to the production of the desired LNT tetrasaccharide Galβ1–3GlcNAcβ1–3Galβ1–4GlcβProN 3 ( 6 ) in 54% yield.…”

Section: Resultsmentioning

confidence: 99%

“…A solution of glycosyl donor 25 (350 mg, 0.46 mmol) and glycosyl acceptor 26 [39] (400 mg, 0.38 mmol) in anhydrous CH 2 Cl 2 (20 mL) was stirred with activated 4 A molecular sieves (0.80 g) under argon for 30 min. The reaction mixture was cooled to −20 °C and NIS (368 mg, 1.64 mmol) was added.…”

Section: Methodsmentioning

confidence: 99%

Chemoenzymatic synthesis of α2–3-sialylated carbohydrate epitopes

Huang

Chen

2011

Sci. China Chem.

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Sialic acids are common terminal carbohydrates on cell surface. Together with internal carbohydrate structures, they play important roles in many physiological and pathological processes. In order to obtain α2–3-sialylated oligosaccharides, a highly efficient one-pot three-enzyme synthetic approach was applied. The P. multocida α2–3-sialyltransferase (PmST1) involved in the synthesis was a multifunctional enzyme with extremely flexible donor and acceptor substrate specificities. Sialyltransferase acceptors, including type 1 structure (Galβ1–3GlcNAcβProN3), type 2 structures (Galβ1–4GlcNAcβProN3 and 6-sulfo-Galβ1–4GlcNAcβProN3), type 4 structure (Galβ1–3GalNAcβProN3), type 3 or core 1 structure (Galβ1–3GalNAcαProN3) and human milk oligosaccharide or lipooligosaccharide lacto-N-tetraose (LNT) (Galβ1–3GlcNAcβ1–3Galβ1–4GlcβProN3), were chemically synthesized. They were then used in one-pot three-enzyme reactions with sialic acid precursor ManNAc or ManNGc, to synthesize a library of natural occurring α2–3-linked sialosides with different internal sugar units. The sialylated oligosaccharides obtained are valuable probes for their biological studies

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Synthesis of propyl and 2-aminoethyl glycosides of α-d-galactosyl-(1→3′)-β-lactoside

Cited by 26 publications

References 21 publications

The design and synthesis of an α-Gal trisaccharide epitope that provides a highly specific anti-Gal immune response

The design and synthesis of an α-Gal trisaccharide epitope that provides a highly specific anti-Gal immune response

Fluorinated organic azides – their preparation and synthetic application

Chemoenzymatic synthesis of α2–3-sialylated carbohydrate epitopes

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