Abstract
We report the automated glycan assembly (AGA) of different oligosaccharide fragments of the bacterial peptidoglycan (PGN) backbone. Iterative addition on a solid support of an acetyl glucosamine and a new muramic acid building block is followed by cleavage from the solid support and final deprotection providing 10 oligosaccharides up to six units.
Highlights
We report the automated glycan assembly (AGA) of different oligosaccharide fragments of the bacterial peptidoglycan (PGN) backbone
Given the biological relevance of these molecules, insight into PGN structure is essential to understand the role of PGNs in pathogenesis, discovering the mechanisms involved in their release, and how they are detected by bacterial versus human host cells.[5]
The two desired building blocks (BB) 1 and 2 are accessible starting from the unprotected glucosamine with a divergent synthetic pathway from glucosamine thioglycoside 3.29 Glycosyl phosphate building block 1 was prepared in nine steps, following published procedures.[28,29,30]
Summary
We report the automated glycan assembly (AGA) of different oligosaccharide fragments of the bacterial peptidoglycan (PGN) backbone. Iterative addition on a solid support of an acetyl glucosamine and a new muramic acid building block is followed by cleavage from the solid support and final deprotection providing 10 oligosaccharides up to six units.
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