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D-半乳糖醛类似物作为大肠杆菌β-D-半乳糖苷酶的竞争性抑制剂和底物的无效性。

The ineffectiveness of analogs of D-galactal as competitive inhibitors of, and substrates for, beta-D-galactosidase from Escherichia coli.

作者信息

Dettinger H M, Kurz G, Lehmann J

出版信息

Carbohydr Res. 1979 Sep;74:301-7. doi: 10.1016/s0008-6215(00)84784-9.

DOI:10.1016/s0008-6215(00)84784-9
PMID:114299
Abstract

2,6-Anhydro-3-deoxy-aldehydo-D-lyxo-hept-2-enose (7) and 2,6-anhydro-3-deoxy-D-lyxo-hept-2-enitol (8) were synthesized as half-chair analogs of D-galactal (1). As 1 is a strong inhibitor of, as well as a substrate for, beta-D-galactosidase from Escherichia coli, the same properties were expected for 7 and 8; however, both were ineffective. This result, together with those of other authors, allows speculative conclusions on the tight binding of 1 to the enzyme only, when water or an alcohol is bound as a co-substrate.

摘要

合成了2,6-脱水-3-脱氧-醛基-D-来苏-2-庚烯糖(7)和2,6-脱水-3-脱氧-D-来苏-2-庚烯醇(8)作为D-半乳糖醛(1)的半椅式类似物。由于1是大肠杆菌β-D-半乳糖苷酶的强抑制剂和底物,预计7和8也具有相同的性质;然而,两者均无效。这一结果与其他作者的结果一起,使得我们可以推测,只有当水或醇作为共底物结合时,1才会与该酶紧密结合。

相似文献

1
The ineffectiveness of analogs of D-galactal as competitive inhibitors of, and substrates for, beta-D-galactosidase from Escherichia coli.D-半乳糖醛类似物作为大肠杆菌β-D-半乳糖苷酶的竞争性抑制剂和底物的无效性。
Carbohydr Res. 1979 Sep;74:301-7. doi: 10.1016/s0008-6215(00)84784-9.
2
Attempted affinity-labelling of beta-D-galactosidase from Escherichia coli with 2,6:3,4-dianhydro-1-deoxy-D-talo-hept-1-enitol.尝试用2,6:3,4-二脱水-1-脱氧-D-塔罗-庚-1-烯醇对大肠杆菌的β-D-半乳糖苷酶进行亲和标记。
Carbohydr Res. 1982 Sep 1;107(1):43-53. doi: 10.1016/s0008-6215(00)80774-0.
3
Evaluation of C-(beta-D-galactosyl) and C-(2-deoxy-D-lyxo-hex-1-enopyranosyl) (D-galactal type) derivatives as inhibitors of beta-D-galactosidase from Escherichia coli.对C-(β-D-半乳糖基)和C-(2-脱氧-D-吡喃己烯糖基)(D-半乳糖烯型)衍生物作为大肠杆菌β-D-半乳糖苷酶抑制剂的评估。
Carbohydr Res. 1996 Sep 23;291:43-52.
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Synthesis of 2,6-anhydro-S-[ethylmercury(II)]-1-thio-D-glycero-L-manno-heptitol+ ++ and bis(2,6-anhydro-1-thio-D-glycero-L-manno-heptitol)mercury(II), and the study of their interaction with beta-D-galactosidase from E. coli.2,6-脱水-S-[乙基汞(II)]-1-硫代-D-甘油-L-甘露庚糖醇及双(2,6-脱水-1-硫代-D-甘油-L-甘露庚糖醇)汞(II)的合成及其与大肠杆菌β-D-半乳糖苷酶相互作用的研究
Carbohydr Res. 1986 Dec 15;158:91-9. doi: 10.1016/0008-6215(86)84008-3.
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Radioaffinity labelling of beta-D-galactosidase from Escherichia coli with [14C]-glycerol, mediated through covalently bound 2,6-anhydro-1-deoxy-D-galacto-hept-1-enitol.通过共价结合的2,6-脱水-1-脱氧-D-半乳糖-庚-1-烯醇介导,用[¹⁴C]-甘油对大肠杆菌β-D-半乳糖苷酶进行放射性亲和标记。
Carbohydr Res. 1982 Nov 16;110(1):181-5. doi: 10.1016/0008-6215(82)85039-8.
6
Affinity labelling of beta-D-galactosidase from Escherichia coli with D-[6-(3)H]-galactal.用D-[6-(3)H]-半乳糖烯对大肠杆菌β-D-半乳糖苷酶进行亲和标记
Carbohydr Res. 1981 Jun 16;93(1):C14-20. doi: 10.1016/s0008-6215(00)80768-5.
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Strong inhibitory effect of furanoses and sugar lactones on beta-galactosidase Escherichia coli.呋喃糖和糖内酯对大肠杆菌β-半乳糖苷酶有强烈抑制作用。
Biochemistry. 1987 Mar 24;26(6):1526-31. doi: 10.1021/bi00380a005.
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Comparison of the beta-galactosidase conformations induced by D-galactal and by magnesium ions.D-半乳糖醛和镁离子诱导的β-半乳糖苷酶构象的比较。
Biochemistry. 1980 Sep 2;19(18):4143-9. doi: 10.1021/bi00559a002.
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Stereochemistry of D-galactal and D-galacto-octenitol hydration by coffee bean alpha-galactosidase: insight into catalytic functioning of the enzyme.咖啡豆α-半乳糖苷酶催化D-半乳糖醛和D-半乳糖辛烯醇水合反应的立体化学:对该酶催化功能的深入了解。
Arch Biochem Biophys. 1992 Feb 1;292(2):493-8. doi: 10.1016/0003-9861(92)90021-n.
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Interaction of the lacZ beta-galactosidase of Escherichia coli with some beta-D-galactopyranoside competitive inhibitors.大肠杆菌乳糖酶β-半乳糖苷酶与某些β-D-吡喃半乳糖苷竞争性抑制剂的相互作用
Biochem J. 1979 Jan 1;177(1):145-52. doi: 10.1042/bj1770145.

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