Chemical Synthesis of the Tumor-Associated Globo H Antigen.

  title={Chemical Synthesis of the Tumor-Associated Globo H Antigen.},
  author={S. S. Mandal and Guochao Liao and Zhongwu Guo},
  journal={RSC advances},
  volume={5 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 cis α-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… Expand
Chemical Synthesis of the Tumor‐Associated Globo H Antigen.
A derivative of the tumor-associated globo H antigen, a complex hexasaccharide, is synthesized by convergent and efficient [3+2+1] strategy using various glycosylation methods.
Chemical synthesis and immunological evaluation of entirely carbohydrate conjugate Globo H-PS A1†
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Pondering the structural factors that affect 1,2-trans-galactosylation: A lesson learnt from 3-O-β-galactosylation of galactosamine
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Automated synthesis of the tumor-associated carbohydrate antigens Gb-3 and Globo-H: incorporation of alpha-galactosidic linkages.
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Linear synthesis of the tumor-associated carbohydrate antigens Globo-H, SSEA-3, and Gb3.
The tumor-associated carbohydrate antigens Globo-H, SSEA-3, and Gb3 were synthesized in a linear fashion using glycosyl phosphate monosaccharide building blocks using a difficult alpha-(1-->4-cis)-galactosidic linkage using a galactosyl phosphate donor with high selectivity. Expand
Enzymatic synthesis of tumor-associated carbohydrate antigen Globo-H hexasaccharide.
This study represents a facile enzymatic synthesis of the Globo-H antigen from the generation of more expensive sugar nucleotides from their corresponding inexpensive C4 epimers. Expand
Total Synthesis and Proof of Structure of a Human Breast Tumor (Globo-H) Antigen
The total synthesis of the Hakomori MBr1 antigen, heavily expressed on human breast tumors, is related. The construction involved the assembly of four glycals:  (17 (twice), 18, 20, and 26) and anExpand
A second generation synthesis of the MBr1 (globo-H) breast tumor antigen: new application of the n-pentenyl glycoside method for achieving complex carbohydrate protein linkages.
A new synthesis of the hexasaccharide MBr1 antigen (globo-H) is reported. A revised construction with improved efficiency was necessary because an anti-cancer vaccine containing this antigen isExpand
A Two-Directional and Highly Convergent Approach for the Synthesis of the Tumor-Associated Antigen Globo-H.
  • Zhu, Boons
  • Medicine, Chemistry
  • Angewandte Chemie
  • 1999
The assembly of six readily available building blocks in five glycosylation steps affords the tumor-associated Globo-H hexasaccharide 1 without the need for any intermediate protecting groupExpand
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Multi-component one-pot synthesis of the tumor-associated carbohydrate antigen Globo-H based on preactivation of thioglycosyl donors.
Two efficient routes for the rapid assembly of the tumor-associated carbohydrate antigen Globo-H hexasaccharide 2 by a preactivation based iterative one-pot strategy are reported, demonstrating that oligosaccharides containing alpha and beta linkages within the same molecule can be constructed in one pot with higher glyco-assembly efficiencies than the automated solid-phase synthesis strategy. Expand
Synthesis of a monophosphoryl lipid A derivative and its conjugation to a modified form of a tumor-associated carbohydrate antigen GM3.
An efficient synthesis of a derivative of monophosphoryl lipid A suitable for coupling to various structures for the construction of glycoconjugate vaccines and its conjugation with an N-modifiedExpand