4.8 Article

Acyl and Silyl Group Effects in Reactivity-Based One-Pot Glycosylation: Synthesis of Embryonic Stem Cell Surface Carbohydrates Lc4 and IV2Fuc-Lc4

Journal

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 134, Issue 10, Pages 4549-4552

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ja300284x

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Funding

  1. National Science Council [NSC 97-2113-M-001-033-MY3, NSC 98-2119-M-001-008-MY2]
  2. Academia Sinica

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Relative reactivity evaluations showed the graded arming of toluenyl thioglucosides by variously positioned silyl groups but not by their acyl counterparts. These findings were applied in reactivity-based one-pot assembly of linker-attached Lc(4) and IV(2)Fuc-Lc(4), which are components of human embryonic stem cell surface. The sugar-galectin-1 binding was also examined.

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