Synthesis of 5-deoxy-β-d-galactofuranosides as tools for the characterization of β-d-galactofuranosidases
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- 作者：Andrea Bordoni ; Rosa M. de Lederkremer ; Carla Marino
- 关键词：5-Deoxy-d-galactofuranosides ; PET deoxygenation ; Galactofuranosidase substrates ; Galactofuranosidase inhibition
- 刊名：Bioorganic and Medicinal Chemistry
- 出版年：2010
- 出版时间：15 July 2010
- 年：2010
- 卷：18
- 期：14
- 页码：5339-5345
- 全文大小：491 K
文摘
Derivatives of 5-deoxy-β-d-galactofuranose (5-deoxy-α-l-arabino-hexofuranose) have been synthesized starting from d-galacturonic acid. The synthesis of methyl 5-deoxy-α-l-arabino-hexofuranoside (14α) was achieved by an efficient strategy previously optimized, involving a photoinduced electron transfer (PET) deoxygenation. Compound 14α was converted into per-O-acetyl-5-deoxy-α,β-l-arabino-hexofuranoside (16), an activated precursor for glycosylation reactions. The SnCl4-promoted glycosylation of 16 led to 4-nitrophenyl (19α), and 4-methylthiophenyl 5-deoxy-α-l-arabino-hexofuranosides (20α). The oxygenated analog 4-methylphenyl 1-thio-β-d-galactofuranoside (23β) was also prepared. The 5-deoxy galactofuranosides were evaluated as inhibitors or substrates of the exo-β-d-galactofuranosidase from Penicillium fellutanum, showing that the absence of HO-5 drastically diminishes the affinity for the protein.