Preparation of core 2 type tetrasaccharide carrying decapeptide by benzyl protection-based solid-phase synthesis strategy

β- d-Gal-(1→4)-β- d-GlcNAc-[β- d-Gal-(1→3)]-α- d-GalNAc-(1→3)- l-Ser/Thr building blocks for solid-phase synthesis of glycopeptide were stereoselectively synthesized in a benzyl-protected form. The key glycosylation reaction to form β- d-GlcNAc linkage was established by the use of protected N-trich...

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Bibliographic Details
Published in:Tetrahedron letters 2002-11, Vol.43 (46), p.8395-8399
Main Authors: Takano, Yutaka, Habiro, Motoki, Someya, Masaomi, Hojo, Hironobu, Nakahara, Yoshiaki
Format: Article
Language:English
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Summary:β- d-Gal-(1→4)-β- d-GlcNAc-[β- d-Gal-(1→3)]-α- d-GalNAc-(1→3)- l-Ser/Thr building blocks for solid-phase synthesis of glycopeptide were stereoselectively synthesized in a benzyl-protected form. The key glycosylation reaction to form β- d-GlcNAc linkage was established by the use of protected N-trichloroacetyl- d-lactosaminyl fluoride. Usefulness of the building block was demonstrated by solid-phase synthesis of a segment of human leukosialin. Benzyl protecting group was efficiently removed by ‘low acidity TfOH’ conditions. Stereocontrolled synthesis of the core 2 tetrasaccharides, solid-phase synthesis of a glycopeptide segment with the tetrasaccharide building block, and efficient removal of the benzyl protecting group are described.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(02)01947-0