Total synthesis of the carbohydrate-protein linkage region common to several mammalian proteoglycans
1993; Elsevier BV; Volume: 244; Issue: 2 Linguagem: Inglês
10.1016/0008-6215(83)85009-5
ISSN1873-426X
AutoresSandrine Rio, Jean‐Marie Beau, Jean‐Claude Jacquinet,
Tópico(s)Carbohydrate Chemistry and Synthesis
ResumoA stereocontrolled synthesis of β-d-GlcpA-(1 → 3)-β-d-Galp-(1 → 3)-β-d-Galp-(1 → 4)-β-d-Xylp-(1 → O)-l-Ser-Gly, the common glycopeptide sequence of the carbohydrate-protein linkage region of most mammalian proteoglycans, was achieved by use of O-[2-(trimethylsilyl)ethyl 2,3,4-tri-O-benzoyl-β-d-glucopyranosyluronate]-(1 → 3)-O-(2,4,6-tri-O-benzoyl-β-d-galactopyranosyl)-(1 → 3)-O-(2,4,6-tri-O-benzoyl-β-d-galactopyranosyl)-(1 → 4)-2,3-di-O-benzoyl-α,β-d-xylopyranosyl trichloroacetimidate as the key intermediate. Condensation of this glycosyl donor with suitably protected l-seryl-glycine dipeptide segments, and peptide chain elongation, allowed the construction in high yield of complex structures of this linkage region.
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