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On the Reactivity of Gulose and Guluronic Acid Building Blocks in the Context of Alginate Assembly
Author(s) -
Zhang Qingju,
van Rijssel Erwin R.,
Overkleeft Herman S.,
van der Marel Gijsbert A.,
Codée Jeroen D. C.
Publication year - 2016
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201600336
Subject(s) - synthon , chemistry , glycosylation , context (archaeology) , reactivity (psychology) , nucleophile , disaccharide , acetal , stereochemistry , combinatorial chemistry , organic chemistry , biochemistry , catalysis , medicine , paleontology , alternative medicine , pathology , biology
A novel set of L ‐gulose and L ‐guluronic acid building blocks, comprising both monosaccharide and disaccharide synthons, was assembled to investigate how structural changes in these synthons influence the outcome of glycosylation reactions in which they are involved. Our studies corroborate previous reports that identified the gulosyl C4‐OH group as a relatively poor nucleophile. We did not find a major influence of the neighboring C5 functionality on the reactivity of the alcohols, and the gulose acceptors did not provide more productive glycosylation reactions than their guluronic acid counterparts. The conformational behavior of the synthons was found to be of prime importance to the outcome of the reactions.