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

Liming Wang | Zendy; Yongzhen Zhang | Zendy; Herman S. Overkleeft | Zendy; Gijsbert A. van der Marel | Zendy; Jeroen D. C. Codée | Zendy

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

Author(s) -

Liming Wang,

Yongzhen Zhang,

Herman S. Overkleeft,

Gijsbert A. van der Marel,

Jeroen D. C. Codée

Publication year - 2020

Publication title -

the journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.2

H-Index - 228

eISSN - 1520-6904

pISSN - 0022-3263

DOI - 10.1021/acs.joc.0c00703

Subject(s) - chemistry , disaccharide , tetrasaccharide , glycosylation , azide , stereochemistry , formamide , reagent , combinatorial chemistry , organic chemistry , biochemistry , polysaccharide

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 Pseudomonas aeruginosa 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- O -DTBS protected galactosyl azide donor.

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