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Concentration Dependence of Glycosylation Outcome: A Clue to Reproducibility and Understanding the Reasons Behind
Author(s) -
Koov Leonid O.,
Malysheva Nelly N.,
Orlova Anna V.,
Zinin Alexander I.,
Laptinskaya Tatiana V.,
Koova Elena G.,
Kolotyrkitalya G.
Publication year - 2012
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.201101613
Subject(s) - chemistry , glycosyl , glycosylation , glycosyl donor , yield (engineering) , disaccharide , reagent , anomer , sialic acid , stereochemistry , organic chemistry , biochemistry , materials science , metallurgy
Changes in the concentration of reagents (0.009–0.2 M ) have been shown to dramatically effect the yield and stereoselectivity of glycosylation with a sialic acid based glycosyl donor in a complex nonlinear manner that correlates with changes in the structures of the supramers of the reagents. The yield of disaccharide gradually increases with concentration and levels off at concentrations of glycosyl donor higher than 69 m M . The ratio of anomers is very high at some concentrations (α/β ≈ 20:1), moderate (α/β ≈ 8:1) or very low (α/β ≈ 4:1) at others. The formation of mixed supramers of glycosyl donor and glycosyl acceptor at concentrations exceeding 69 m M was detected by polarimetry and laser light scattering.