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Stereoselective Synthesis of L ‐Guluronic Acid Alginates
Author(s) -
Dinkelaar Jasper,
van den Bos Leendert J.,
Hogendorf Wouter F. J.,
Lodder Gerrit,
Overkleeft Herman S.,
Codée Jeroen D. C.,
van der Marel Gijsbert A.
Publication year - 2008
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200800960
Subject(s) - stereoselectivity , glycosidic bond , trisaccharide , glycosylation , chemistry , nucleophile , stereochemistry , combinatorial chemistry , biochemistry , enzyme , catalysis
The glycosylation properties of gulopyranosides have been mapped out, and it is shown that gulose has an intrinsic preference for the formation of 1,2‐c is ‐glycosidic bonds. It is postulated that this glycosylation behaviour originates from nucleophilic attack at the oxacarbenium ion, which adopts the most favourable 3 H 4 conformation. Building on the stereoselectivity of gulose, a guluronic acid alginate trisaccharide was assembled for the first time by using gulopyranosyl building blocks.