158194-79-7Relevant articles and documents
Synthetic studies of glycosyl serines in the carbohydrate-protein region of protoglycans
Tamura, Jun-Ichi,Neumann, Klaus W.,Ogawa, Tomoya
, p. 1239 - 1257 (2007/10/03)
A series of glycosyl serines 1-6 which are located in the carbohydrate-protein linkage region of proteoglycans, including the chondroitin penta- and heptasaccharides GalNAcα(1-4)R (3), GalNAcβ(1-4)R (4) and GalNAcβ(1-4)GlcAβ(1-3)GalNAc(1-4)R (6) as well as the heparin pentasaccharide GlcNAcα(1-4)R (5) [R = GlcAβ(1-3)Galβ(1-3)Galβ(1-4)Xylβ-Ser] were systematically synthesized as follows. Trisaccharide acceptor 27 having a Gal(1-3)Galβ(1-4)Xyl sequence was glycosylated with di- and tetrasaccharide donors 16α, 16β, 22, and 26, which correspond to the non-reducing end sequences of 3-6, regio- and stereoselectively to afford penta- and heptasaccharides 30, 34, 36, and 39, respectively. After the conversion into the respective penta- and heptaosylimidates 42c-f as well as tri- and tetraosylimidates 42a and b, they were coupled with serine derivative 43 to give tri-, tetra-, penta-, and heptaosyl serines 44a-f. All the glycosyl serines were deprotected to 1-6. VCH Verlagsgesellschaft mbH, 1996.