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学科主题: 生命有机化学
题名: Synthesis, Evaluation, and Mechanism of N,N,N-Trimethyl-D-glucosamine-(1 -> 4)-chitooligosaccharides as Selective Inhibitors of Glycosyl Hydrolase Family 20 beta-N-Acetyl-D-hexosaminidases
其他题名: 以糖基邻炔基苯甲酸酯为给体的金催化糖苷化反应合成人参皂甙Rh2和chikusetsusaponin- LT8
作者: Yang Y(杨友) ; Liu, Tian ; Yang, Yongliang ; Wu, Qingyue ; Yang, Qing ; Yu B(俞飚)
刊名: ChemBioChem
发表日期: 2011
卷: 12, 期:3, 页:457-467
收录类别: SCI
部门归属: 中科院上海有机化学研究所; 大连理工大学; 华东理工大学
英文摘要: GH20 beta-N-acetyl-D-hexosaminidases are enzymes involved in many vital processes. Inhibitors that specifically target GH20 enzymes in pests are of agricultural and economic importance. Structural comparison has revealed that the bacterial chitindegrading beta-N-acetyl-D-hexosaminidases each have an extra +1 subsite in the active site; this structural difference could be exploited for the development of selective inhibitors. N,N,N-trimethyl-D-glucosamine (TMG)-chitotriomycin, which contains three GlcNAc residues, is a natural selective inhibitor against bacterial and insect beta-N-acetyl-D-hexosaminidases. However, our structural alignment analysis indicated that the two GlcNAc residues at the reducing end might be unnecessary. To prove this hypothesis, we designed and synthesized a series of TMG-chitotriomycin analogues containing one to four GlcNAc units. Inhibitory kinetics and molecular docking showed that TMG-(GlcNAc)(2) , is as active as TMG-chitotriomycin [TMG-(GlcNAc)(3)]. The selective inhibition mechanism of TMG-chitotriomycin was also explained.
语种: 英语
相关网址: 查看原文
WOS记录号: WOS:000287718700019
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内容类型: 期刊论文
URI标识: http://ir.sioc.ac.cn/handle/331003/19135
Appears in Collections:生命有机化学国家重点实验室_期刊论文

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Recommended Citation:
Yang Y,Liu, Tian,Yang, Yongliang,et al. Synthesis, Evaluation, and Mechanism of N,N,N-Trimethyl-D-glucosamine-(1 -> 4)-chitooligosaccharides as Selective Inhibitors of Glycosyl Hydrolase Family 20 beta-N-Acetyl-D-hexosaminidases[J]. ChemBioChem,2011,12(3):457-467.
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