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Reagent Controlled Glycosylations for the Assembly of Well-Defined Pel Oligosaccharides.

ABSTRACT: A new additive, methyl(phenyl)formamide (MPF), is introduced for the glycosylation of 2-azido-2-deoxyglucose building blocks. A linear ?-(1,4)-glucosamine tetrasaccharide was assembled to prove the utility of MPF. Next, a hexasaccharide fragment of the Pseudomonas aeruginosa exopolysaccharide Pel was assembled using a [2 + 2 + 2] strategy modulated by MPF. The used [galactosazide-?-(1,4)-glucosazide] disaccharide building blocks were synthesized using a 4,6-O-DTBS protected galactosyl azide donor.

SUBMITTER: Wang L

PROVIDER: S-EPMC7754192 | biostudies-literature | 2020 Dec

REPOSITORIES: biostudies-literature

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Reagent Controlled Glycosylations for the Assembly of Well-Defined Pel Oligosaccharides.

Wang Liming L Zhang Yongzhen Y Overkleeft Herman S HS van der Marel Gijsbert A GA Codée Jeroen D C JDC

The Journal of organic chemistry 20200518 24

A new additive, methyl(phenyl)formamide (MPF), is introduced for the glycosylation of 2-azido-2-deoxyglucose building blocks. A linear α-(1,4)-glucosamine tetrasaccharide was assembled to prove the utility of MPF. Next, a hexasaccharide fragment of the <i>Pseudomonas aeruginosa</i> exopolysaccharide Pel was assembled using a [2 + 2 + 2] strategy modulated by MPF. The used [galactosazide-α-(1,4)-glucosazide] disaccharide building blocks were synthesized using a 4,6-<i>O</i>-DTBS protected galacto ...[more]

PMID: 32375481

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