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Synthesis of the 3'-O-sulfated TF antigen with a TEG-N₃ linker for glycodendrimersomes preparation to study lectin binding.

ABSTRACT: The synthesis of gram quantities of the TF antigen (β-ᴅ-Gal-(1→3)-α-ᴅ-GalNAc) and its 3'-sulfated analogue with a TEG-N₃ spacer attached is described. The synthesis of the TF antigen comprises seven steps, from a known N-Troc-protected galactosamine donor, with an overall yield of 31%. Both the spacer (85%) and the galactose moiety (79%) were introduced using thioglycoside donors in NIS/AgOTf-promoted glycosylation reactions. The 3'-sulfate was finally introduced through tin activation in benzene/DMF followed by treatment with a sulfur trioxide-trimethylamine complex in a 66% yield.

SUBMITTER: Reihill M

PROVIDER: S-EPMC10840529 | biostudies-literature | 2024

REPOSITORIES: biostudies-literature

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Synthesis of the 3'-O-sulfated TF antigen with a TEG-N3 linker for glycodendrimersomes preparation to study lectin binding.

Reihill Mark M Ma Hanyue H Bengtsson Dennis D Oscarson Stefan S

Beilstein journal of organic chemistry 20240130

The synthesis of gram quantities of the TF antigen (β-ᴅ-Gal-(1→3)-α-ᴅ-GalNAc) and its 3'-sulfated analogue with a TEG-N3 spacer attached is described. The synthesis of the TF antigen comprises seven steps, from a known N-Troc-protected galactosamine donor, with an overall yield of 31%. Both the spacer (85%) and the galactose moiety (79%) were introduced using thioglycoside donors in NIS/AgOTf-promoted glycosylation reactions. The 3'-sulfate was finally introduced through tin ac ...[more]

PMID: 38318459

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