Synthesis of Pentasaccharide Repeating Unit Corresponding to the Cell Wall O-Polysaccharide of Salmonella enterica O55 Strain Containing a Rare Sugar 3-Acetamido-3-deoxy-d-fucose
نویسندگان
چکیده
Abstract A pentasaccharide repeating unit corresponding to the cell wall O-antigen of Salmonella enterica O55 containing a rare sugar, 3-acetamido-3-deoxy-d-fucose has been synthesized as its p-methoxyphenyl glycoside using sequential stereoselective glycosylation strategy. suitably functionalized 3-azido-3-deoxy-d-fucose thioglycoside derivative was prepared in very good yield and used reaction. Functionalized monosaccharide intermediates were judiciously stereoselectively assembled get desired excellent yield.
منابع مشابه
Convergent Synthesis of Oligosaccharide Fragments Corresponding to the Cell Wall O‐Polysaccharide of Salmonella enterica O53
Conventional glycoconjugate vaccines are prepared with polysaccharides isolated from bacterial fermentation, an approach with some significant drawbacks such as handling of live bacterial strains, the presence of biological impurities, and inter-batch variations in oligosaccharide epitope structure. However, it has been shown in many cases that a synthetic fragment of appropriate structure conj...
متن کاملExpedient Synthesis of the Pentasaccharide Repeating Unit of the Polysaccharide O‐Antigen of Escherichia coli O11
A convergent [3+2] block synthetic strategy was developed for the synthesis of the pentasaccharide repeating unit of the cell wall O-antigen of Escherichia coli O11 strain in excellent yield in a minimum number of steps. Several suitably functionalized thioglycoside derivatives were used as glycosyl donors during the synthesis of the target compound. A thioglycoside was the glycosyl donor used ...
متن کاملEfficient Synthesis of the Pentasaccharide Repeating Unit of the O-Antigenic Polysaccharide of Escherichia coli O166 Strain
An efficient strategy has been developed for the synthesis of the pentasaccharide repeating unit of the cell-wall polysaccharide of Escherichia coli O166 strain through sequential stereoselective glycosylations of monosaccharide intermediates. All the glycosylation steps were high-yielding with high stereoselectivities.
متن کاملTowards inhibitors of glycosyltransferases: A novel approach to the synthesis of 3-acetamido-3-deoxy-D-psicofuranose derivatives
A novel synthetic strategy leading to 3-acetamido-3-deoxy-D-psicofuranose 9 is presented. The latter compound, after some manipulations, was transformed into fully protected 3-acetamido-3-deoxy-D-psicofuranose 11 as a potential substrate for the synthesis of N-acetylglucosaminyltransferase inhibitors designed by computational methods. After the attempted thioglycosylation of 11 with EtSH in the...
متن کاملSynthesis of the Heptasaccharide Repeating Unit of the Cell Wall O‐Polysaccharide of Enterotoxigenic Escherichia coli O139
Enterotoxigenic Escherichia coli (ETEC) like the O139 strain are mostly responsible for traveler's diarrhea and causes diseases in pigs, cattle, and poultry. A convenient synthetic strategy was developed for the synthesis of the heptasaccharide repeating unit of the cell wall lipopolysaccharide of the E. coli O139 strain. The p-methoxybenzyl (PMB) group was used as a temporary protecting group ...
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
ژورنال
عنوان ژورنال: Synthesis
سال: 2021
ISSN: ['1791-5155', '1791-5856']
DOI: https://doi.org/10.1055/s-0037-1610777