New Thioglycoside Development towards O-Glycosylation
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1
Louisiana State University, United States
Chemical synthesis of oligosaccharides is a significant tool for deepening our understanding of glycobiology due to the microheterogeneity of natural oligosaccharides. In particular, O-glycosylation is one of the most important chemical reactions in multistep synthesis of oligosaccharides. Two classes of most commonly used electrophiles in O-glycosylation are thioglycosides and glycosyl trichloroacetimidates (TCAs). Both the thioglycosides and TCAs are easily synthesized. However, thioglycosides require harsh activation conditions due to the high stability, while TCAs are not easily carried through multistep synthesis despite easy activation under mildly acidic conditions. Recently, our group developed two new classes of thioglycosides: 4-(4-methoxyphenyl)-3-butenylthioglycosides (MBTGs) and 4-(4-methoxyphenyl)-4-pentenylthioglycosides (MPTGs), which merge the merits of stability of common thioglycoside and easy activation of TCAs. In contrast to most thioglycoside activation methods, photoinduced activation of MBTGs and acid-catalyzed activation of both MBTGs and MPTGs tolerate more functionalities. Further, MPTG donors showed higher reactivity toward very hindered acceptors.
Keywords:
Organic Chemistry,
carbohydrate chemistry,
Photo chemistry,
Thioglycoside,
O-glycosylation
Conference:
National Organization for the Professional Advancement of Black Chemists and Chemical Engineers (NOBCChE) 45th Annual Conference , Orlando, Florida, United States, 17 Sep - 20 Sep, 2018.
Presentation Type:
Poster Presentation
Topic:
Organic Chemistry
Citation:
Du
S,
Lacey
KD,
Quarels
RD and
Ragains
JR
(2019). New Thioglycoside Development towards O-Glycosylation.
Front. Chem.
Conference Abstract:
National Organization for the Professional Advancement of Black Chemists and Chemical Engineers (NOBCChE) 45th Annual Conference .
doi: 10.3389/conf.fchem.2018.01.00014
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Received:
26 Sep 2018;
Published Online:
17 Jan 2019.
*
Correspondence:
Dr. Justin R Ragains, Louisiana State University, Baton Rouge, United States, jragains@lsu.edu