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A Modular Chemoenzymatic Synthesis of Disialosyl Globopentaosylceramide (DSGb5Cer) Glycan.
Wu, Dung-Yeh; Adak, Avijit K; Kuo, Yan-Ting; Shen, Yu-Ju; Li, Pei-Jhen; Hwu, Jih Ru; Lin, Chun-Cheng.
Afiliación
  • Wu DY; Department of Chemistry, National Tsing Hua University, Hsinchu 30013, Taiwan.
  • Adak AK; Department of Chemistry, National Tsing Hua University, Hsinchu 30013, Taiwan.
  • Kuo YT; Department of Chemistry, National Tsing Hua University, Hsinchu 30013, Taiwan.
  • Shen YJ; Department of Chemistry, National Tsing Hua University, Hsinchu 30013, Taiwan.
  • Li PJ; Department of Chemistry, National Tsing Hua University, Hsinchu 30013, Taiwan.
  • Hwu JR; Department of Chemistry, National Tsing Hua University, Hsinchu 30013, Taiwan.
  • Lin CC; Department of Chemistry, National Tsing Hua University, Hsinchu 30013, Taiwan.
J Org Chem ; 85(24): 15920-15935, 2020 12 18.
Article en En | MEDLINE | ID: mdl-32567311
The total synthesis of the oligosaccharide moiety of disialosyl globopentaosylceramide (DSGb5 Cer), a dominant ganglioside isolated from malignant renal cell carcinoma tissues, is reported. The synthetic strategy relies on a chemical α(2,6)-sialylation at the internal GalNAc unit of a Gb5 pentasaccharide backbone that furnishes a Neu5Acα(2,6)GalNAc-linked hexasaccharide, suitable for an enzymatic α(2,3)-sialylation of the terminal Gal residue to construct a heptasaccharide glycan. Convergent access to this key α(2,6)-sialylated hexasaccharide was also achieved through a [3+3] glycosylation building upon a Galß(1,3)[Neu5Acα(2,6)]GalNAc-based trisaccharide donor and a Gb3 acceptor. The synthetic DSGb5 glycan bearing a 6-azidohexyl aglycon at the reducing end could undergo further regioselective functionalization. This approach represents a viable chemoenzymatic method for accessing complex ganglioside glycans and should be useful for the synthesis and biological investigation of DSGb5 derivatives.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Polisacáridos / Globósidos Idioma: En Revista: J Org Chem Año: 2020 Tipo del documento: Article País de afiliación: Taiwán Pais de publicación: Estados Unidos
Texto completo
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XML
PubMed Links
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Polisacáridos / Globósidos Idioma: En Revista: J Org Chem Año: 2020 Tipo del documento: Article País de afiliación: Taiwán Pais de publicación: Estados Unidos