Zur Synthese von Glucosiden und von nicht‐reduzierenden Disacchariden

Helferich, Burckhardt; Weis, K.

doi:10.1002/cber.19560890220

Cited by 182 publications

(35 citation statements)

References 8 publications

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“…The 2 ,3 ,4 ,6 -tetra-O-acetyl-α-Dglucopyranosyl bromide (AcGBr) was synthesized from glucose by acetylation and bromination according to the method of Kartha et al (13); it was allowed to react with HEA in the presence of HgBr 2 by the published procedure of Helferich et al (14) to give AcGEA. SA) were obtained by radical polymerization of AcGEA or its copolymerization with SA using AIBN as an initiator in benzene at 60…”

Section: Preparation Of Acgea Pgea and P(gea-co-sa)mentioning

confidence: 99%

Self-Association of Poly[2-(β-D-glucosyloxy)ethyl Acrylate] in Water

Liang

2000

Journal of Colloid and Interface Science

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Section: Preparation Of Acgea Pgea and P(gea-co-sa)mentioning

confidence: 99%

Self-Association of Poly[2-(β-D-glucosyloxy)ethyl Acrylate] in Water

Liang

2000

Journal of Colloid and Interface Science

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“…[17] Subsequent acidolysis, acetylation and treatment with HBr in glacial acetic acid afforded the galactosyl donor 10 in 70 % yield over three steps after column chromatography. Stereoselective coupling of 10 with Fmoc-Thr(a-4,6-O-Bzn-GalNAc)-OtBu (7) was achieved most successfully by the Helferich method [18] with microwave assistance. Thus, on irradiation of the acceptor 7 with 6-deoxy-6-fluorogalactosyl bromide (10) and Hg(CN) 2 in MeNO 2 /CH 2 Cl 2 3:2 at 100 W (80 8C) a clean conversion into the b-configured disaccharide 17 (98 %) was observed without significant formation of orthoester or a-configured byproducts.…”

Section: Resultsmentioning

confidence: 99%

Fluorinated Glycosyl Amino Acids for Mucin‐Like Glycopeptide Antigen Analogues

Wagner

Mersch

Hoffmann‐Röder

2010

Chemistry A European J

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The aberrant glycosylation profiles of mucin glycoproteins on epithelial tumour cells represent attractive target structures for the development of immunotherapy against cancer. Mucin-type glycopeptides have been successfully investigated as molecularly defined vaccine prototypes for triggering humoral immunity but are susceptible to rapid in vivo degradation. As a potential means to enhance the bioavailabilities of the antigenic structures, hydrolysis-resistant carbohydrate analogues with fluorine substituents at positions C6, C2' and C6' were synthesised and incorporated into the tandem repeat sequence of the mucin MUC1. The resulting pseudo-glycopeptides can be used to elucidate the effects of chemically modified antibody determinants on metabolic and immunological properties.

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“…In contrast to conventional glycoside syntheses, the stereoselective synthesis of non-reducing disaccharides demands for control of stereochemistry at two anomeric centers. [8][9][10][11][12][13][14][15][16][17][18][19][20][21] Accordingly, many syntheses of non-reducing disaccharides lead to mixtures of stereoisomers. In addition, yields in the formation of 1-1 0 -linked disaccharides significantly exceed 50% only in rare cases.…”

Section: Introductionmentioning

confidence: 99%