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Synthetic Studies of Glycosyl Serines in the Carbohydrate‐Protein Region of Protoglycans
Author(s) -
Tamura JunIchi,
Neumann Klaus W.,
Ogawa Tomoya
Publication year - 1996
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.199619960804
Subject(s) - tetrasaccharide , chemistry , trisaccharide , glycosyl , stereochemistry , serine , glycosyl donor , carbohydrate , biochemistry , polysaccharide , phosphorylation
A series of glycosyl serines 1–6 which are located in the carbohydrate‐protein linkage region of proteoglycans, including the chondrottin penta‐ and heptasaccharides GalNAcα(1–4)R ( 3 ), GalNAcß(1–4)R ( 4 ) and GalNAcß(1–4)GlcAß(1–3)GalNAc(1–4)R ( 6 ) as well as the heparin pentasaccharide GlcNAcα(1–4)R ( 5 ) [R = GlcAß(1–3)Galß(1–3)Galß(1–4)Xylß‐Ser] were systematically synthesized as follows. Trisaccharide acceptor 27 having a Gal(1–3)Galß(1–4)Xyl sequence was glycosylated with di‐ and tetrasaccharide donors 16α, 16ß, 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 .