The synthesis and characterization of α- and (β-L-fucopyranosyl phosphates and GDP fucose
The synthesis and characterization of α- and (β-L-fucopyranosyl phosphates and GDP fucose
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α-和(β-L-吡喃岩藻糖基磷酸盐和 GDP 岩藻糖的合成和表征
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发表时间：
1981
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通讯作者：
R. Barker
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文献类型：
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作者：
H. Nunez;J. O'connor;P. Rosevear;R. Barker
二磷酸鸟苷岩藻糖 (GDPFuc) 已通过岩藻糖化学合成，总产率为 40%。通过利用鸟苷 5'-磷酸二正丁基硫代膦酸酐（Furusawa 等人 J. Chem. Soc. Perkin Trans I, 171 (1976)），将关键中间体 β-L-吡喃岩藻糖基磷酸盐的产量提高到之前报道的产量的五倍（Prihar and Behrman. Biochemistry, 12, 997 (1973)），从而使该合成成为可能。或GMP吗啉用于合成GDPFuc，并通过改进分离中间体和最终产物的方法。在 pH 3 时，GDPFuc 降解为 GDP，半衰期在 37 °C 下为 7 h，在 4 °C 下为 52 h。 pH 值在 5 到 8 之间时，7 天后降解率不到 10%。 pH 7.5 的 0.2 M PIPES 缓冲液中的 20 mMMn2+ 和 Mg2+ 均不会刺激 GDPFuc 的水解。异核、C-P 和 H-P 偶联常数表明 β-L-吡喃岩藻糖基磷酸酯和 GDPFuc 中磷酸部分的优先位置都是反式至 C-2。在核糖部分...
Guanosine diphosphate fucose (GDPFuc) has been synthesized chemically in an overall yield of 40% from fucose. This synthesis was made possible by increasing the yield of the key intermediate, β-L-fucopyranosyl phosphate, five-fold over that previously reported (Prihar and Behrman. Biochemistry, 12, 997 (1973)), by utilizing guanosine 5′-phosphoric di-n-butylphosphinothioic anhydride (Furusawa et al. J. Chem. Soc. Perkin Trans I, 171 (1976)) or GMP morpholdate for the synthesis of GDPFuc, and by improving the method of isolating intermediates and the final product. At pH 3, GDPFuc is degraded to GDP with a half-life of 7 h at 37 °C and 52 h at 4 °C. At pH values between 5 and 8, less than 10% is degraded after 7 days. Neither 20 mM Mn2+ nor Mg2+ in 0.2 M PIPES buffer at pH 7.5 stimulate the hydrolysis of GDPFuc. Heteronuclear, C–P and H–P coupling constants indicate that the preferential position of the phosphate moiety in both β-L-fucopyranosyl phosphate and GDPFuc is trans to C-2. In the ribose moiety of...