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Chemical Synthesis of the Tumor-Associated Globo H Antigen.

ABSTRACT: A derivative of the tumor-associated globo H antigen, a complex hexasaccharide, was synthesized by a convergent and efficient [3+2+1] strategy using various glycosylation methods. All glycosylation reactions afforded good to excellent yields and outstanding stereoselectivity, including the installation of cis ?-linked D-galactose and L-fucose. The longest linear sequence for this synthesis was 11 steps from a galactose derivative 11 to give an overall yield of 2.6%. The synthetic target had a free and reactive amino group at the glycan reducing end, facilitating its conjugation with other molecules for various applications.

SUBMITTER: Mandal SS

PROVIDER: S-EPMC4527582 | biostudies-literature | 2015 Jan

REPOSITORIES: biostudies-literature

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Chemical Synthesis of the Tumor-Associated Globo H Antigen.

Mandal Satadru S SS Liao Guochao G Guo Zhongwu Z

RSC advances 20150101 30

A derivative of the tumor-associated globo H antigen, a complex hexasaccharide, was synthesized by a convergent and efficient [3+2+1] strategy using various glycosylation methods. All glycosylation reactions afforded good to excellent yields and outstanding stereoselectivity, including the installation of <i>cis</i> α-linked D-galactose and L-fucose. The longest linear sequence for this synthesis was 11 steps from a galactose derivative <b>11</b> to give an overall yield of 2.6%. The synthetic t ...[more]

PMID: 26257889

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Chemoenzymatic Syntheses of Tumor-Associated Carbohydrate Antigen Globo-H and Stage-Specific Embryonic Antigen 4.

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Multi-component one-pot synthesis of the tumor-associated carbohydrate antigen Globo-H based on preactivation of thioglycosyl donors.

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