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首页> 外文期刊>The Journal of Antibiotics: An International Journal >Selective catalytic hydrogenation of the N-acyl and uridyl double bonds in the tunicamycin family of protein N-glycosylation inhibitors
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Selective catalytic hydrogenation of the N-acyl and uridyl double bonds in the tunicamycin family of protein N-glycosylation inhibitors

机译：蛋白质N-糖基化抑制剂杂交族族族酰基和尿苷双键的选择性催化氢化

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摘要

Tunicamycin is a Streptomyces-derived inhibitor of eukaryotic protein N-glycosylation and bacterial cell wall biosynthesis, and is a potent and general toxin by these biological mechanisms. The antibacterial activity is dependent in part upon a pi-pi stacking interaction between the tunicamycin uridyl group and a specific Phe residue within MraY, a tunicamycin-binding protein in bacteria. We have previously shown that reducing the tunicamycin uridyl group to 5,6-dihydrouridyl (DHU) significantly lowers its eukaryotic toxicity, potentially by disrupting the p-stacking with the active site Phe. The present report compares the catalytic hydrogenation of tunicamycin and uridine with various precious metal catalysts, and describe optimum conditions for the selective production of N-acyl reduced tunicamycin or for tunicamycins reduced in both the N-acyl and uridyl double bonds. At room temperature, Pd-based catalysts are selective for the N-acyl reduction, whereas Rh-based catalysts favor the double reduction to provide access to fully reduced tunicamycin. The reduced DHU is highly base-sensitive, leading to amide ring opening under mild alkaline conditions.
机译：Tunicamycin是一种真核蛋白N-糖基化和细菌细胞壁生物合成的链霉菌衍生的抑制剂，并且通过这些生物机制是一种有效和一般的毒素。抗菌活性部分地依赖于唐尼霉素尿苷基与MRAY内的特定PHE残基之间的PI-PI堆叠相互作用，细菌中的唐氏霉素结合蛋白。我们之前已经表明，将唐菊尼霉素尿苷基降至5,6-二氢脲（DHU）显着降低其真核毒性，可能通过破坏与活性位点PHE的p堆叠。本报告比较了宫霉素和尿苷与各种贵金属催化剂的催化氢化，并描述了在N-酰基和尿苷中减少的唐氏霉素或少尼霉素的选择性生产的最佳条件。在室温下，Pd基催化剂是对N-酰基还原的选择性，而基于RH的催化剂有利于双重减少，以提供对完全减少的unicicamycin的访问。降低的DHU是高度基础敏感的，导致在轻度碱性条件下的酰胺环开口。

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