Synthesis of some partially substituted methyl α-d- and phenyl 1-thio-α-d-mannopyranosides for the preparation of manno-oligosaccharides

Szurmai, Zoltán; Balatoni, Lajos; Lipták, András

doi:10.1016/0008-6215(94)84264-7

Cited by 27 publications

(19 citation statements)

References 12 publications

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“…8 -COOH (compound 9) were synthesized from compound 1 ( Fig. 1), prepared from D-mannose (D-Man) by previously published methods (32,46) by using the sulfoxide strategy recently applied to the construction of ␤-manno linkages by Crich and Sun (10). This glycosylation method is compatible with the presence of a thiophenyl group in the acceptor and thus allows convergent blockwise synthesis of the tetrasaccharide (compound 7).…”

Section: Methodsmentioning

confidence: 99%

Synthetic Analogues of β-1,2 Oligomannosides Prevent Intestinal Colonization by the Pathogenic Yeast Candida albicans

Dromer

Chevalier

Sendid

et al. 2002

Antimicrob Agents Chemother

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The pathogenic yeast Candida albicans displays at its cell surface ␤-1,2 oligomannosides (␤-1,2-Mans). In contrast to the ubiquitous ␣-Mans, ␤-1,2-Mans bind to galectin-3, a major endogenous lectin expressed on epithelial cells. The specific role of ␤-1,2-Mans in colonization of the gut by C. albicans was assessed in a mouse model. A selected virulent strain of C. albicans (expressing more ␤-1,2-Man epitopes) induced more intense and sustained colonization than an avirulent strain (expressing less ␤-1,2-Man epitopes). Synthetic (⌺) ␤-and ␣-linked tetramannosides with antigenicities that mimicked the antigenicities of C. albicans-derived oligomannosides were then constructed. Oral administration of ⌺␤-1,2-Man (30 mg/kg of body weight) prior to inoculation with the virulent strain resulted in almost complete eradication of yeasts from stool samples, whereas administration of ⌺␣-Man at the same dose did not. As most cases of human systemic candidiasis are endogenous in origin, this first demonstration that a synthetic analogue of a yeast adhesin can prevent yeast colonization in the gut opens the possibility of new prophylactic strategies.

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Section: Methodsmentioning

confidence: 99%

Synthetic Analogues of β-1,2 Oligomannosides Prevent Intestinal Colonization by the Pathogenic Yeast Candida albicans

Dromer

Chevalier

Sendid

et al. 2002

Antimicrob Agents Chemother

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“…Both the 1 H and the 13 C NMR spectra showed the presence of two SPh groups and the 3-O-benzyl group, and the 4,6-O-benzylidene skeleton was also present. The simple NMR spectra did not provide sufficient information about the configuration of either C-2 or the anomeric carbon.…”

Section: Resultsmentioning

confidence: 97%

“…Compound 6 (481 mg, 1 mmol) was converted using method B to give a mixture of 12 and 13 which were separated by silica gel chromatography (hexane/EtOAc 9:1 and CH 2 Cl 2 /EtOAc 99. 5 9 Hz, H-2), 2.71 (q, 2H, CH 2 ), 1.25 (t, 3H, CH 3 ); 13 Compound 6 (481 mg, 1 mmol) was converted using method C to give a mixture of 13, 14, and 15 which were separated by silica gel chromatography (hexane/EtOAc 9:1 and CH 2 Cl 2 /hexane 8:2). Compound 13 was isolated with 8% yield (26 mg).…”

Section: General Methods E For the Synthesis Of Methyl Glycosides (21-23)mentioning

confidence: 99%

Reactions of phenyl and ethyl 2-O-sulfonyl-1-thio-α-d-manno- and β-d-glucopyranosides with thionucleophiles

Lipták¹,

Lázár²,

Borbás³

et al. 2009

Carbohydrate Research

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“…In the first step, we submitted methyl mannopyranoside to a double benzylidenation by slightly modifying a previously reported procedure described by Liptak and co-workers. [23] We obtained product 12 after chromatographic purification as an almost equimolar diasteroisomeric mixture (endo/exo = 1.2:1). It is well established by several precedents [24,25] that the reductive opening of fivemembered benzylidenes displays complementary regioselectivity according to the configuration of the starting material.…”

Section: Resultsmentioning

confidence: 99%

One‐Pot Catalytic Glycosidation/Fmoc Removal – An Iterable Sequence for Straightforward Assembly of Oligosaccharides Related to HIV gp120

et al. 2010

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The removal of a transient Fmoc protecting group can be simply performed by the addition of excess Et3N just after the accomplishment of a Bi(OTf)3‐promoted glycosidation reaction. The obtained oligosaccharide can be directly employed as a glycosyl acceptor for further elongation of the saccharide. The preparation of biologically important, linear and branched mannans incorporated into HIV gp120 demonstrates that the iteration of this one‐pot sequence leads to a very straightforward oligosaccharide assembly.

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Synthesis of some partially substituted methyl α-d- and phenyl 1-thio-α-d-mannopyranosides for the preparation of manno-oligosaccharides

Cited by 27 publications

References 12 publications

Synthetic Analogues of β-1,2 Oligomannosides Prevent Intestinal Colonization by the Pathogenic Yeast Candida albicans

Synthetic Analogues of β-1,2 Oligomannosides Prevent Intestinal Colonization by the Pathogenic Yeast Candida albicans

Reactions of phenyl and ethyl 2-O-sulfonyl-1-thio-α-d-manno- and β-d-glucopyranosides with thionucleophiles

One‐Pot Catalytic Glycosidation/Fmoc Removal – An Iterable Sequence for Straightforward Assembly of Oligosaccharides Related to HIV gp120

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