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THIO-CLICK CHEMISTRY IN
GLYCOSCIENCE: OVERVIEW
AND PERSPECTIVES
ZBIGNIEW J. WITCZAK
2.1
INTRODUCTION
The new concept by Sharpless, Finn, and Kolb for conducting organic reactions capa-
ble of producing wide libraries of fully functionalized synthetic molecules has been
classified as click chemistry. The traditional azide-alkyne click chemistry approaches
with multiple types of clickable functional groups were the leading examples of the
early strategy.
Recently, thiol-ene chemistry became a well-accepted part of the click reaction
toolbox and is rapidly developing in many strategic areas of thio-conjugation. In
carbohydrate chemistry the most important substrates are glycosyl thiols. Few years
ago, they became available in both anomeric forms, which created new opportunities
for the expansion of the existing techniques for thio-conjugation to form products
deriving from both stereo isomers.
2.2 THIO-BASED CLICK REACTIONS
The addition of a thiol to the double bond is known as the thiol-ene reaction. The scope
of the thiol-ene approach is quite impressive with respect to the endless applicability
of reactive thiols and almost all molecules with a double bond (ene) moiety. The
reactions take place under various experimental conditions, such as, base or acid
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