Glycosides of 8-hydroxy-3,6-dioxaoctanal. A synthesis of a new spacer for synthetic oligosaccharides

Vérez-Bencomo, Vicente; Campos-Valdes, Maria T.; Mariño-Albernas, Jose R.; Fernandez-Santana, Violeta; Hernandez-Rensoli, Marilyn; Pérez–Martínez, Carlos

doi:10.1016/0008-6215(91)84138-5

Cited by 14 publications

(6 citation statements)

References 13 publications

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“…(2,3,4,6-tetra-O-acetyl-fl-D-glucopyranosyl-3,6,9,12-tetraoxatetradecanoate (4). (6). Analytical data: calculated for C38HssO24, C 50.8, H 6.50; found, C 50.6, H 6.44.…”

Section: General Procedures For Synthesis Of the Spacer 91ycosides 3-6mentioning

confidence: 95%

“…tn the synthesis of neoglycoconjugates many different spacer molecules and coupling methods have been employed [3,4]. Presently, spacer molecules derived from oligoethylene glycols have gained in interest, owing to their hydrophilic nature, and are frequently utilized [5][6][7]. Oligosaccharides with an ethylene glycol spacer have been synthesized and exploited by Verez-Bencomo et at.…”

Section: Introductionmentioning

confidence: 99%

“…Oligosaccharides with an ethylene glycol spacer have been synthesized and exploited by Verez-Bencomo et at. [51 and by Bertozzi and Bednarski [6], who used an aldehydo and an amino group, respectively, for the further coupling into glycoconjugates. We now describe the synthesis of ethylene glycol glycosides with a carboxylic acid as functional group.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of oligosaccharides with oligoethylene glycolspacers and their conversion into glycoconjugates usingN,N,N ? ,N ? -tetramethyl(succinimido)u roniu mtetrafluoroborate as coupling reagent

1993

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Glycosides of glucose and lactose with di-and tetraethytene glycols, transformed into bifunctional (alcohol, ester) spacer molecules, have been synthesized. After deprotection, these spacer glycosides, containing a free carboxyl group, have been transformed efficiently into glycoconjugates using N, N,N',N'-tetramethyl(succinimido)uronium tetrafluoroborate (TSTU) for the formation of an active ester.

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“…(2,3,4,6-tetra-O-acetyl-fl-D-glucopyranosyl-3,6,9,12-tetraoxatetradecanoate (4). (6). Analytical data: calculated for C38HssO24, C 50.8, H 6.50; found, C 50.6, H 6.44.…”

Section: General Procedures For Synthesis Of the Spacer 91ycosides 3-6mentioning

confidence: 95%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Synthesis of oligosaccharides with oligoethylene glycolspacers and their conversion into glycoconjugates usingN,N,N ? ,N ? -tetramethyl(succinimido)u roniu mtetrafluoroborate as coupling reagent

1993

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“…The optimum length of the aglycon chain was determined to be 8-carbon. Polyethyleneglycol glycosides containing an 61-cyclic acetal (Verez-Bencomo et al, 1991) and polyethyleneglycol glycosides having a terminal carboxyl group (Andersson et al, 1993) have been described recently. The structures of these glycosides are shown in Fig.…”

Section: Glycosides With O-aldehydo or O-carboxyl Groupmentioning

confidence: 99%

Neoglycoconjugates

Lee¹,

Lee²

1996

Glycosciences

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“…Monotosylate 2 was prepared from 1 in only 40% yield (TsCl, 1.0 equiv, Et 3 N, CH 2 Cl 2 ) owing to the simultaneous formation of undesired ditosylate. According to a published procedure, , oxidation (DMSO, P 2 O 5 , CH 2 Cl 2 ) and acetal formation (HOCH 2 CH 2 OH, p TsOH, PhH) were performed in good yields ( 3 , 92%; 4 , 89%). After azide displacement and reduction [(i) NaN 3 , EtOH; (ii) H 2 , 10% Pd−C, EtOH], amine 6 was obtained in 23% overall yield from 1 .…”

mentioning

confidence: 99%

Chemical Modification of Chitosan. 3. Hyperbranched Chitosan−Sialic Acid Dendrimer Hybrid with Tetraethylene Glycol Spacer

2000

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Chitosan is a polysaccharide composed mainly of β-(1-4)-2-amino-2-deoxy-D-glucopyranose repeating units. Chitosan shows interesting biological properties such as immunological, 1 antibacterial, 2,3 and wound healing activity. 4 Moreover, it is a nontoxic 3 and biodegradable polymer, 5 and the free amino groups of chitosan offer great potential for further derivatization. Alternatively, dendrimers also offer several possibilities in molecular design owing to their multifunctional attachment sites. They have been used to scaffold neoglycoconjugates, 6 probes, catalysts, and so on. 7 Herein we report the preparation of sialic acid bound dendronized 8 chitosandendrimer hybrids. These molecules may have the potential to inhibit the hemagglutination of human erythrocytes by influenza virus hemagglutinin as recently observed with straight polymers and hyperbranched polymers. 6 As polymer backbones used so far are highly toxic, it is expected that scaffolding poly-(amidoamine) (PAMAM) dendrimer onto nontoxic chitosan core would present biopharmaceutical advantage.To build up the desired long spacer necessary to allow multiple branch construction, commercial tetraethylene glycol 1 was modified into aminoacetal 6 in five steps (Scheme 1). Monotosylate 2 was prepared from 1 in only 40% yield (TsCl, 1.0 equiv, Et 3 N, CH 2 Cl 2 ) owing to the simultaneous formation of undesired ditosylate. According to a published procedure, 9,10 oxidation (DMSO, P 2 O 5 , CH 2 Cl 2 ) and acetal formation (HOCH 2 CH 2 OH, pTsOH, PhH) were performed in good yields (3, 92%; 4, 89%). After azide displacement and reduction [(i) NaN 3 , EtOH; (ii) H 2 , 10% Pd-C, EtOH], 11 amine 6 was obtained in 23% overall yield from 1. Using 6 as an amine source, poly(amidoamine) (PAMAM) dendrimers were prepared according to Tomalia et al. 12 by repeating cycle of methyl acrylate and ethylenediamine treatment. The methyl esters of each dendrimers 7a-c (G ) 0.5, 1.5, 2.5) were purified by silica gel column chromatography (CH 2 Cl 2 / MeOH ) 10/1) which were obtained in moderate to good yields (7a, G ) 0.5, 70%; 7b, G ) 1.5, 73%; 7c, G ) 2.5, 57%). The terminal amines of each generation (G ) 1, G ) 2, and G ) 3, 8a-c) were obtained from each methyl esters quantitatively by treatment with excess ethylenediamine at room temperature for 3 days.The sialic acid residues were initially attached onto each dendrimer by reductive N-alkylation with known p-formylphenyl R-sialoside 9 13 using NaCNBH 3 in methanol (Scheme 2). 14 Since 3 equiv of aldehyde 9 was used

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Glycosides of 8-hydroxy-3,6-dioxaoctanal. A synthesis of a new spacer for synthetic oligosaccharides

Cited by 14 publications

References 13 publications

Synthesis of oligosaccharides with oligoethylene glycolspacers and their conversion into glycoconjugates usingN,N,N ? ,N ? -tetramethyl(succinimido)u roniu mtetrafluoroborate as coupling reagent

Synthesis of oligosaccharides with oligoethylene glycolspacers and their conversion into glycoconjugates usingN,N,N ? ,N ? -tetramethyl(succinimido)u roniu mtetrafluoroborate as coupling reagent

Neoglycoconjugates

Chemical Modification of Chitosan. 3. Hyperbranched Chitosan−Sialic Acid Dendrimer Hybrid with Tetraethylene Glycol Spacer

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