The synthesis of complex carbohydrates containing sialic acid is very challenging by chemical methods, in part due to the competing elimination reaction, as well as poor stereocontrol. One major disadvantage in the field is the limited knowledge of the mechanism of sialylations. The mechanism is believed to go through an oxacarbenium ion intermediate. Recent findings suggest the existence of an all-axial conformation of the oxacarbenium ion that might be important in controlling the overall efficiency of sialylations. As a part of a general research goal to gain a better understanding of sialylations, we describe herein the synthesis of a C-3 deuterium-labeled substrate that might give insight on the existence of such conformation.
|Advisor:||De Meo, Cristina|
|Commitee:||Dixon, Robert, Luesse, Sarah|
|School:||Southern Illinois University at Edwardsville|
|School Location:||United States -- Illinois|
|Source:||MAI 53/03M(E), Masters Abstracts International|
|Subjects:||Biochemistry, Organic chemistry|
|Keywords:||Deuterium, Modification, Sialic, Synthesis|
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