The use of the novel glycosyl acceptor and supramer analysis in the synthesis of sialyl-α(2–3)-galactose building block

Nagornaya, Marina O.; Orlova, A. V.; Stepanova, Elena V.; Zinin, Alexander I.; Laptinskaya, T. V.; Kononov, L. O.

doi:10.1016/j.carres.2018.10.001

Cited by 14 publications

(41 citation statements)

References 62 publications

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“…However, acidities of 4‐methoxyphenol ( 2 c ) and 4‐methylphenol ( 2 d ) are similar [39] suggesting that it is not acidity/basicity of a phenol that determines its reactivity/nucleophilicity under conditions of PTC sialylation. More reasonable seems to be a possibility of formation of tight [22a,30] (hence less reactive) hydrogen bonded supramers of para ‐alkoxy‐substituted phenols 2 a – c due to the presence of an additional hydrogen bond accepting site (alkoxy group).…”

Section: Resultsmentioning

confidence: 99%

Black Swan in Phase Transfer Catalysis: Influence of Mixing Mode on the Stereoselectivity of Glycosylation

et al. 2022

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Phase transfer catalysis (PTC) is widely used for the preparation of anomerically pure aryl glycosides by glycosylation of phenols with glycosyl halides. Here, we attempted to synthesize 4‐(3‐chloropropoxy)phenyl (CPP) sialoside – a useful Janus glycoside for neoglycoconjugate synthesis. A batch glycosylation reaction under typical PTC conditions (N‐acetylsialyl chloride, 4‐(3‐chloropropoxy)phenol, Bu4NHSO4, AcOEt, 10 % aq Na2CO3) resulted in formation of CPP sialoside as a single anomer, albeit in low yield. Conversely, the PTC glycosylation in flow using Comet X‐01 micromixer doubled the yield of CPP sialoside, which was obtained as a mixture of anomers suggesting the change in the reaction mechanism apparently induced by the change in mixing mode. An increase in flow rate led to further loss of stereoselectivity while the use of T‐shaped mixer increased stereoselectivity. Similar results were obtained for N,N‐diacetylsialyl chloride and two other para‐alkoxy‐substituted phenols suggesting generality of the discovered phenomenon.

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Section: Resultsmentioning

confidence: 99%

Black Swan in Phase Transfer Catalysis: Influence of Mixing Mode on the Stereoselectivity of Glycosylation

et al. 2022

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“…We have recently argued [105][106][107] that the sometimes observed profound influence of the nature of the (functionalized) aglycon in a glycosyl acceptor may be related to the formation of reaction solutions with modified structures featuring different supramolecular assemblies of the reagents (supramers [104]) in solution. In a similar fashion, solutions of Ara 6 C 2 NH 2 -GNPs 3 with the shorter and more hydrophobic С 2 spacer aglycon might form tighter [108][109][110] supramers in aqueous solution [104,111,112], which eventually would form more clustered Ara 6 -glycan domains on the surface of Ara 6 -GNPs. The results obtained clearly suggest that the choice of the spacer aglycon may be critical for the specificity of antibodies against the corresponding glyco-GNPs and the studies in this direction seem promising.…”

Section: Discussionmentioning

confidence: 99%

Preparation and in vivo evaluation of glyco-gold nanoparticles carrying synthetic mycobacterial hexaarabinofuranoside

Burygin¹,

Abronina²,

Podvalnyy³

et al. 2020

Beilstein J. Nanotechnol.

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A number of bacterial glycans are specific markers for the detection and the serological identification of microorganisms and are also widely used as antigenic components of vaccines. The use of gold nanoparticles as carriers for glyco-epitopes is becoming an important alternative to the traditional conjugation with proteins and synthetic polymers. In this study, we aimed to prepare and evaluate in vivo glyco-gold nanoparticles (glyco-GNPs) bearing the terminal-branched hexaarabinofuranoside fragment (Ara6) of arabinan domains of lipoarabinomannan and arabinogalactan, which are principal polysaccharides of the cell wall of Mycobacterium tuberculosis, the causative agent of tuberculosis. In particular, we were interested whether the antibodies generated against Ara6-GNPs would recognize the natural saccharides on the cell surface of different mycobacterial strains. Two synthetic Ara6 glycosides with amino-functionalized spacer aglycons differing in length and hydrophilicity were directly conjugated with spherical gold nanoparticles (d = 15 nm) to give two sets of glyco-GNPs, which were used for the immunization of rabbits. Dot assays revealed cross-reactions between the two obtained antisera with the hexaarabinofuranoside and the 2-aminoethyl aglycon used for the preparation of glyco-GNPs. Both antisera contained high titers of antibodies specific for Mycobacteria as shown by enzyme-linked immunosorbent assay using M. bovis and M. smegmatis cells as antigens while there was only a weak response to M. phlei cells and no interaction with E. coli cells. The results obtained suggest that glyco-GNPs are promising agents for the generation of anti-mycobacterial antibodies.

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“…The coincidence of "critical" temperatures for aqueous solutions of two different derivatives of carbohydrates [43,44], apparently, indicates a common cause of this phenomenon. It is possible that jump-like changes in the specific optical rotation of aqueous carbohydrate solutions with a change in temperature reflect significant changes in the structure of water [45,46], and the molecules of chiral solutes (carbohydrates) act as "probes" that "sense" the slightest changes in their conformation or rearrangement of the microenvironment (in the solvation "shell"), which at the macroscopic level is manifested as a change in the magnitude of the specific rotation (see [19,26] and references cited therein).…”

Section: (Black Circles) and Day 3 (Blue Triangles) Solution # 3 At mentioning

confidence: 99%

“…This new type of "weak" (judging by the magnitude of the interaction energy, which does not exceed k B T [17]), but the extremely effective and spontaneous structuring of liquids has not attracted the attention of researchers for a long time. Only recently has its importance been identified for an adequate description of reactions and other chemical processes [8,9,13,14,[18][19][20][21][22][23][24][25][26][27][28][29].…”

Section: Introductionmentioning

confidence: 99%

Polarimetry as a method for studying the structure of aqueous carbohydrate solutions: correlation with other methods

Orlova¹,

Kononov²

2020

RENSIT

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The review provides data indicating that polarimetry is a sensitive tool for studying the structure of aqueous carbohydrate solutions. Using aqueous solutions of D-levoglucosan (1,6-anhydro-D-glucopyranose) as an example, it was demonstrated, using polarimetry, quantum chemical calculations, HPLC, static and dynamic light scattering, that polarimetry allows one to detect changes in the structure of solutions with changes in concentration and temperature, as well as the evolution of the structure of solutions over time. In particular, the phenomenon of the existence of "critical" concentrations and temperatures was discovered at which the specific rotation of the solutions undergo jump-like changes, apparently reflecting rearrangements in the structure of the solution. It is also possible that in the case of aqueous solutions, chiral carbohydrate molecules might act as "probes" that "sense" the slightest changes in their conformation or rearrangement of the environment (in the solvation shell) caused by changes in the structure of water, which at the macroscopic level manifests themselves as change in specific rotation.

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The use of the novel glycosyl acceptor and supramer analysis in the synthesis of sialyl-α(2–3)-galactose building block

Cited by 14 publications

References 62 publications

Black Swan in Phase Transfer Catalysis: Influence of Mixing Mode on the Stereoselectivity of Glycosylation

Black Swan in Phase Transfer Catalysis: Influence of Mixing Mode on the Stereoselectivity of Glycosylation

Preparation and in vivo evaluation of glyco-gold nanoparticles carrying synthetic mycobacterial hexaarabinofuranoside

Polarimetry as a method for studying the structure of aqueous carbohydrate solutions: correlation with other methods

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