作为一类基于机制的内切β-N-乙酰氨基葡萄糖苷酶抑制剂的寡糖噻唑啉的合成及抑制活性
Synthesis and inhibitory activity of oligosaccharide thiazolines as a class of mechanism-based inhibitors for endo-beta-N-acetylglucosaminidases.
作者信息
Li Bing, Takegawa Kaoru, Suzuki Tadashi, Yamamoto Kenji, Wang Lai-Xi
机构信息
Institute of Human Virology, University of Maryland School of Medicine, Baltimore, MD 21201, USA.
出版信息
Bioorg Med Chem. 2008 Apr 15;16(8):4670-5. doi: 10.1016/j.bmc.2008.02.032. Epub 2008 Feb 14.
Abstract
A facile synthesis of oligosaccharide-thiazoline derivatives of N-glycans as a novel class of inhibitors for endo-beta-N-acetylglucosaminidases was described. It was found that the external sugar residues on the N-glycan core could enhance the inhibitory potency. While the Manbeta1,4GlcNAc- and Man3GlcNAc-thiazolines were only moderate inhibitors, the large Man9GlcNAc-thiazoline demonstrated potent inhibitory activity, with an IC(50) of 0.22 and 0.42 microM against the Arthrobacter enzyme (Endo-A) and the human endo-beta-N-acetylglycosaminidase (hENGase), respectively. It was also observed that the oligosaccharide thiazolines could differentially inhibit endo-beta-N-acetylglucosaminidases from different sources. These oligosaccharide thiazolines represent the first class of endo-beta-N-acetylglucosaminidase inhibitors.
摘要
描述了一种简便合成N-聚糖的寡糖-噻唑啉衍生物的方法，该衍生物是一类新型的内切β-N-乙酰氨基葡萄糖苷酶抑制剂。发现N-聚糖核心上的外部糖残基可增强抑制效力。虽然Manβ1,4GlcNAc-和Man3GlcNAc-噻唑啉只是中等强度的抑制剂，但较大的Man9GlcNAc-噻唑啉表现出强大的抑制活性，对节杆菌酶（内切-A）和人内切β-N-乙酰氨基葡萄糖苷酶（hENGase）的IC50分别为0.22和0.42微摩尔。还观察到寡糖噻唑啉可以不同程度地抑制来自不同来源的内切β-N-乙酰氨基葡萄糖苷酶。这些寡糖噻唑啉代表了第一类内切β-N-乙酰氨基葡萄糖苷酶抑制剂。
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