5-epi-deoxyrhamnojirimycin is a potent inhibitor of an alpha-L-rhamnosidase: 5-epi-deoxymannojirimycin is not a potent inhibitor of an alpha-D-mannosidase

Davis BG.; Smith C.; Nash RJ.; Watson AA.; Winkler DA.; Griffiths RC.; Fleet GWJ.; Hull A.

首页> 外文期刊>Tetrahedron, Asymmetry: The International Journal for Repid Publication on all Aspects of Asymmetry in Orgainc, Inorganic, Organometallic, Physical and Bio-Organic Chemistry >5-epi-deoxyrhamnojirimycin is a potent inhibitor of an alpha-L-rhamnosidase: 5-epi-deoxymannojirimycin is not a potent inhibitor of an alpha-D-mannosidase

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5-epi-deoxyrhamnojirimycin is a potent inhibitor of an alpha-L-rhamnosidase: 5-epi-deoxymannojirimycin is not a potent inhibitor of an alpha-D-mannosidase

机译：5-epi-deoxyrhamnojirimycin是强力的α-L-鼠李糖苷酶抑制剂：5-epi-deoxyrhamnojirimycin不是强力的α-D-甘露糖苷酶抑制剂

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Whereas deoxyrhamnojirimycin (LRJ) 1 shows no significant inhibition of naringinase (an alpha-L-rhamnosidase), its C-5 epimer 2 is a potent and specific inhibitor of the enzyme and demonstrates the value of unambiguous chemical synthesis of such materials in the evaluation of their biological properties. In contrast, moderately weak inhibition towards an alpha-D-mannosidase is shown by both deoxymannojirimycin (DMJ) 5 and its C-5 epimer 6. Mimics of L-rhamnose which are recognised by enzymes that synthesise or process L-rhamnose may inhibit el ther the biosynthesis of the sugar or its incorporation into mycobacterial cell walls, providing new strategies for the treatment of diseases such as tuberculosis and leprosy. Molecular modelling studies provide a rationale for the surprisingly potent activity of the C-S epimer 2 compared with LRJ 1 and support a general hypothesis that potent piperidine glycosidase inhibitors mimic the H-4(3) conformation Of the relevant glycopyranosyl cation intermediate. (C) 1998 Elsevier Science Ltd. All rights reserved. [References: 72]

机译：脱氧鼠李糖霉素（LRJ）1没有表现出对柚皮苷酶（α-L-鼠李糖苷酶）的明显抑制作用，而其C-5差向异构体2是该酶的有效抑制剂，在评估中证明了此类材料的明确化学合成价值它们的生物学特性。相反，脱氧甘露糖霉素（DMJ）5及其C-5差向异构体6均显示出对α-D-甘露糖苷酶的中等弱抑制作用。L-鼠李糖的模拟物被合成或加工L-鼠李糖的酶识别，可能抑制糖的生物合成或将其掺入分枝杆菌细胞壁，为结核病和麻风病等疾病的治疗提供了新的策略。分子模型研究为C-S差向异构体2与LRJ 1相比具有令人惊讶的有效活性提供了理论基础，并支持了一个通用的假设，即有效的哌啶糖苷酶抑制剂模拟相关糖吡喃糖基阳离子中间体的H-4（3）构象。（C）1998 Elsevier ScienceLtd。保留所有权利。 [参考：72]

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《Tetrahedron, Asymmetry: The International Journal for Repid Publication on all Aspects of Asymmetry in Orgainc, Inorganic, Organometallic, Physical and Bio-Organic Chemistry》 |1998年第16期|共14页
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Davis BG.; Smith C.; Nash RJ.; Watson AA.; Winkler DA.; Griffiths RC.; Fleet GWJ.; Hull A.;
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1. 5-epi-deoxyrhamnojirimycin is a potent inhibitor of an alpha-L-rhamnosidase: 5-epi-deoxymannojirimycin is not a potent inhibitor of an alpha-D-mannosidase [J] . Davis BG., Smith C., Nash RJ., Tetrahedron, Asymmetry: The International Journal for Repid Publication on all Aspects of Asymmetry in Orgainc, Inorganic, Organometallic, Physical and Bio-Organic Chemistry . 1998,第16期

机译：5-epi-deoxyrhamnojirimycin是强力的α-L-鼠李糖苷酶抑制剂：5-epi-deoxyrhamnojirimycin不是强力的α-D-甘露糖苷酶抑制剂
2. Looking glass inhibitors: both enantiomeric N-benzyl derivatives of 1,4-dideoxy-1,4-imino-D-lyxitol [a potent competitive inhibitor of alpha-D-galactosidase] and of 1,4-dideoxy-1,4-imino-L-lyxitol [a weak competitive inhibitor of alpha-D-galactosidase] inhibit naringinase, an alpha-L-rhamnosidase competitively [J] . Mercer TB, Jenkinson SF, Bartholomew B, Tetrahedron, Asymmetry: The International Journal for Repid Publication on all Aspects of Asymmetry in Orgainc, Inorganic, Organometallic, Physical and Bio-Organic Chemistry . 2009,第20期

机译：窥镜抑制剂：1,4-二脱氧-1,4-亚氨基-D-木糖醇[α-D-半乳糖苷酶的有效竞争抑制剂]和1,4-二脱氧-1,4-的对映体N-苄基衍生物亚氨基-L-糖醇（α-D-半乳糖苷酶的弱竞争抑制剂）可抑制naringinase（一种α-L-鼠李糖苷酶）。
3. Synthesis of potent alpha-D-mannosidase and alpha-L-fucosidase inhibitors: 4-amino-4-deoxy-D-erythrose and 4-amino-4,5-dideoxy-L-lyxose [J] . Joubert M., Tarnus C., Streith J., Synlett . 2000,第9期

机译：有效的α-D-甘露糖苷酶和α-L-岩藻糖苷酶抑制剂的合成：4-氨基-4-脱氧-D-赤藓糖和4-氨基-4,5-二脱氧-L-山梨糖
4. Development and characterization of potent peptide inhibitors of p60~(C-Src) PTK using pseudosubstrate-based inhibitor design approach [C] . Jayesh R.Kamath, Ruiwu Liu, Amanda M.Enstrom, the International Peptide Symposium . 2001

机译：基于假素抑制剂设计方法的P60〜（C-SRC）PTK有效肽抑制剂的开发与表征
5. P27 as a molecular target for cancer therapeutics: Discovering small molecule inhibitors of p27 proteolysis and structure-activity relationship and mechanistic studies of largazole, a potent inhibitor of histone deacetylase . [D] . Ungermannova, Dana. 2010

机译：P27作为癌症治疗的分子靶标：发现p27蛋白水解和结构活性关系的小分子抑制剂以及组蛋白脱乙酰基酶的有效抑制剂largazole的机理研究。
6. Influence of elastin on the inhibition of leucocyte elastase by alpha 1-proteinase inhibitor and bronchial inhibitor. Potent inhibition of elastin-bound elastase by bronchial inhibitor. [O] . M Bruch, J G Bieth 1986

机译：弹性蛋白对α1-蛋白酶抑制剂和支气管抑制剂抑制白细胞弹性蛋白酶的影响。支气管抑制剂有效抑制弹性蛋白结合的弹性蛋白酶。
7. Discovery of O 6 -benzyl glaziovianin A, a potent cytotoxic substance and a potent inhibitor of α,β-tubulin polymerization [O] . Ichiro Hayakawa, Shuya Shioda, Takumi Chinen, 2016

机译：发现O 6-苄基glaziovian A，有效的细胞毒性物质和α，β-微管蛋白聚合的有效抑制剂

5-epi-deoxyrhamnojirimycin is a potent inhibitor of an alpha-L-rhamnosidase: 5-epi-deoxymannojirimycin is not a potent inhibitor of an alpha-D-mannosidase

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