1. Solid-Phase Synthesis of Fluorinated Analogues of Glycosyl 1-Phosphate Repeating Structures from Leishmania using the Phosphoramidite Method
- Author
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Ayumu Ishii, Katsuya Takeda, Aya Yaoita, Satoshi Kobayashi, Mihoko Noro, Hideyuki Imoto, Michi Sano, Rintaro Iwata Hara, Hiroaki Ueki, Kazuki Sato, and Takeshi Wada
- Subjects
Phosphoramidite ,biology ,010405 organic chemistry ,Chemistry ,General Chemistry ,010402 general chemistry ,Phosphate ,Leishmania ,biology.organism_classification ,01 natural sciences ,Combinatorial chemistry ,0104 chemical sciences ,carbohydrates (lipids) ,chemistry.chemical_compound ,Solid-phase synthesis ,Glycosyl - Abstract
Bacterial and protozoan sugar chains contain glycosyl 1-phosphate repeating structures; these repeating structures have been studied for vaccine development. The fluorinated analogues of [β-Gal-(1→4)-α-Man-(1→6)-P-] n , which are glycosyl 1-phosphate repeating structures found in Leishmania, were synthesised using the solid-phase phosphoramidite method. This method has been less extensively studied for the synthesis of glycosyl 1-phosphate units than H-phosphonate chemistry. A stepwise synthesis of a compound containing five such repeating units has been conducted using the phosphoramidite method herein, which is the longest glycosyl 1-phosphate structures to be chemically constructed in a stepwise manner.
- Published
- 2018
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