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Solid-Phase Synthesis of Fluorinated Analogues of Glycosyl 1-Phosphate Repeating Structures from Leishmania using the Phosphoramidite Method.

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 [?-Gal-(1?4)-?-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.

SUBMITTER: Hara RI 

PROVIDER: S-EPMC5987806 | biostudies-other | 2018 Jun

REPOSITORIES: biostudies-other

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Solid-Phase Synthesis of Fluorinated Analogues of Glycosyl 1-Phosphate Repeating Structures from <i>Leishmania</i> using the Phosphoramidite Method.

Hara Rintaro Iwata RI   Yaoita Aya A   Takeda Katsuya K   Ueki Hiroaki H   Ishii Ayumu A   Imoto Hideyuki H   Kobayashi Satoshi S   Sano Michi M   Noro Mihoko M   Sato Kazuki K   Wada Takeshi T  

ChemistryOpen 20180430 6

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-] <sub><i>n</i></sub> , which are glycosyl 1-phosphate repeating structures found in <i>Leishmania</i>, were synthesised using the solid-phase phosphoramidite method. This method has been less extensively studied for the synthesis of glycosyl 1-phosphate units than <i>H</i>-phosphonate  ...[more]

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