Stereoselective syntheses of 1,2-trans-related 1-thioglycoses

Defaye, J.; Driguez, Hugues; Ohleyer, E.; Orgeret, C.; Viet, C.

doi:10.1016/0008-6215(84)85288-x

Cited by 41 publications

(12 citation statements)

References 16 publications

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“…The general route leading to the S‐glycosyl analogues 25 – 27 and 29 , designed to prevent potential glycosidase‐catalyzed hydrolysis, is shown in Scheme . The first step was a one‐pot de‐S‐acetylation and thioalkylation of thioacetyl mannopyranoside 19 . This protocol led to 20 after conversion of the alcohol group into a bromo substituent by treatment with carbon tetrabromide and triphenylphosphine.…”

Section: Resultsmentioning

confidence: 99%

The Antiadhesive Strategy in Crohn′s Disease: Orally Active Mannosides to Decolonize Pathogenic Escherichia coli from the Gut

et al. 2016

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Blocking the adherence of bacteria to cells is an attractive complementary approach to current antibiotic treatments, which are faced with increasing resistance. This strategy has been particularly studied in the context of urinary tract infections (UTIs), in which the adhesion of pathogenic Escherichia coli strains to uroepithelial cells is prevented by blocking the FimH adhesin expressed at the tips of bacteria organelles called fimbriae. Recently, we extended the antiadhesive concept, showing that potent FimH antagonists can block the attachment of adherent-invasive E. coli (AIEC) colonizing the intestinal mucosa of patients with Crohn's disease (CD). In this work, we designed a small library of analogues of heptyl mannoside (HM), a previously identified nanomolar FimH inhibitor, but one that displays poor antiadhesive effects in vivo. The anomeric oxygen atom was replaced by a sulfur or a methylene group to prevent hydrolysis by intestinal glycosidases, and chemical groups were attached at the end of the alkyl tail. Importantly, a lead compound was shown to reduce AIEC levels in the feces and in the colonic and ileal mucosa after oral administration (10 mg kg(-1) ) in a transgenic mouse model of CD. The compound showed a low bioavailability, preferable in this instance, thus suggesting the possibility of setting up an innovative antiadhesive therapy, based on the water-soluble and non-cytotoxic FimH antagonists developed here, for the CD subpopulation in which AIEC plays a key role.

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Section: Resultsmentioning

confidence: 99%

The Antiadhesive Strategy in Crohn′s Disease: Orally Active Mannosides to Decolonize Pathogenic Escherichia coli from the Gut

et al. 2016

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“…Because they can be selectively cleaved to form the thiol in the presence of ester protecting groups, almost only thiourea salts and thioacetates have been used as intermediates in the synthesis of anomeric thiols. [18,17,[19][20][21][22][23][24][25][26] In this work, we present the effective synthesis of the tetraxylan 1, which bears a glycosidic thiolinkage on the first glycosidic bond from the non-reducing end by using both mentioned synthetic strategies. Moreover, a comparison between the two mentioned methods for preparing thiolinkages with a special focus on the challenges encountered and main byproducts is also presented.…”

Section: Introductionmentioning

confidence: 99%

Convergent strategy for the synthesis of S-linked oligoxylans

Bonora

Boos

Clausen

2017

Carbohydrate Research

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Arabinoxylans (AX) are a major class of hemicellulose and an important polysaccharide component of lignocellulosic biomass. To utilize the glycan polymer effectively, it is desirable to learn more about the enzymatic hydrolysis of AXs. Well-defined glycans can help to elucidate these processes. Here, we report the efficient synthesis of a mixed O- and S-linked tetraxylan. This thio-oligosaccharide has been developed as a putative inhibitor of arabinoxylan degrading enzymes used for the saccharification of biomass. Two common approaches for the synthesis of thio-oligosaccharides, either involving 1-thioglycoside donors or thioacceptors, are presented and compared regarding byproduct formation and yields. Both methods have shown to be useful for the synthesis of thiolinkages in oligoxylans assembly. However, the success of the reaction is highly dependent on the "match" between donors and acceptors.

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“…2,3,4,6-Tetra-Oacetyl-1-S-acetyl-α-D-mannopyranose (AcManSAc) was prepared by modifying the procedure of the zirconium chloridecatalyzed thiolysis of glucose. 42 Based upon the 1 H NMR spectroscopy of AcManSAc (see Experimental section), it is clear that a mannopyranose in the compound has chair conformation type α-4 C 1 . Also, the presence of the α-anomeric form of the mannopyranose in AcManSAc has been established based on 1 H NMR as well as single crystal X-ray study.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Photophysical Properties of S-Mannosylated Chlorins and Their Effect on Photocytotoxicity in HeLa Cells

Moriwaki

Sawada

Akiyama

et al. 2018

Bulletin of the Chemical Society of Japan

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SMan and H 2 TFPC-SGlc were tested in HeLa cells. These compounds showed no cytotoxicity in the dark. Upon photoirradiation, these compounds killed almost all of the cells in the region of a 1 to 2¯M concentration. The photocytotoxicity of the compounds completely disappeared in the concentration region of 0 to 0.1¯M. The photocytotoxicity of H 2 TFPCSMan is significantly higher than that of H 2 TFPC-SGlc in the concentration range from 0.2 to less than 1¯M. The cellular uptake of H 2 TFPC-SMan in HeLa cells was estimated in terms of fluorescence intensity from each HeLa cell. The cellular uptake of H 2 TFPC-SMan is significantly higher than that of H 2 TFPC-SGlc at a concentration of 0.5¯M. These results are consistent with the experimental observation that the photocytotoxicity of H 2 TFPC-SMan is significantly higher than that of H 2 TFPC-SGlc in a concentration range from 0.2 to less than 1¯M.

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Stereoselective syntheses of 1,2-trans-related 1-thioglycoses

Cited by 41 publications

References 16 publications

The Antiadhesive Strategy in Crohn′s Disease: Orally Active Mannosides to Decolonize Pathogenic Escherichia coli from the Gut

The Antiadhesive Strategy in Crohn′s Disease: Orally Active Mannosides to Decolonize Pathogenic Escherichia coli from the Gut

Convergent strategy for the synthesis of S-linked oligoxylans

Synthesis and Photophysical Properties of S-Mannosylated Chlorins and Their Effect on Photocytotoxicity in HeLa Cells

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