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Synthesis of mucin-type O-glycan probes as aminopropyl glycosides.

ABSTRACT: The chemical synthesis of a series of mucin-type oligosaccharide fragments 1-7 containing an ?-linked aminopropyl spacer ready for glycoarray attachment is reported. A highly convergent and stereoselective strategy that employs two different orthogonal protected galactosamine building blocks was used to access all of the targets. A tandem deprotection sequence, that did not require chromatography-based purification between steps, was employed to globally unmask all protecting groups and all final targets were isolated in good to excellent yields.

SUBMITTER: Benito-Alifonso D

PROVIDER: S-EPMC3778329 | biostudies-literature | 2013

REPOSITORIES: biostudies-literature

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Synthesis of mucin-type O-glycan probes as aminopropyl glycosides.

Benito-Alifonso David D Jones Rachel A RA Tran Anh-Tuan AT Woodward Hannah H Smith Nichola N Galan M Carmen MC

Beilstein journal of organic chemistry 20130913

The chemical synthesis of a series of mucin-type oligosaccharide fragments 1-7 containing an α-linked aminopropyl spacer ready for glycoarray attachment is reported. A highly convergent and stereoselective strategy that employs two different orthogonal protected galactosamine building blocks was used to access all of the targets. A tandem deprotection sequence, that did not require chromatography-based purification between steps, was employed to globally unmask all protecting groups and all fina ...[more]

PMID: 24062854

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