糖苷酶催化糖基氟化物的水解反应。
The hydrolysis of glycosyl fluorides by glycosidases.
作者信息
Barnett J E, Jarvis W T, Munday K A
出版信息
Biochem J. 1967 Nov;105(2):669-72. doi: 10.1042/bj1050669.
Abstract
- alpha-d- and beta-d-Glucopyranosyl, alpha-d- and beta-d-galactopyranosyl, alpha-d-mannopyranosyl and alpha-d-xylopyranosyl fluorides were hydrolysed specifically by the respective glycosidases from several sources. 2. Use of specific inhibitors with a mixture of glycosidases from Helix pomatia intestinal juice showed that each glycosyl fluoride was hydrolysed only by the respective glycosidase. alpha-d-Glucopyranosidase and alpha-d-xylopyranosidase activities were shown to be due to different enzymes. 3. Partially purified enzyme preparations containing only one of the glycosidase activities hydrolysed only the corresponding glycosyl fluoride. 4. The configuration at C-1 of alpha-d-mannopyranosyl fluoride was confirmed since it was hydrolysed by an alpha-d-mannosidase preparation that contained no detectable beta-d-mannosidase activity. 5. An attempt to prepare o-nitrophenyl beta-d-mannopyranoside led only to o-nitrophenyl alpha-d-mannopyranoside.
摘要
- α-D-和β-D-吡喃葡萄糖基、α-D-和β-D-吡喃半乳糖基、α-D-甘露吡喃糖基和α-D-木吡喃糖基氟化物被来自多种来源的相应糖苷酶特异性水解。2. 将特异性抑制剂与来自苹果螺肠液的糖苷酶混合物一起使用表明，每种糖基氟化物仅被相应的糖苷酶水解。已证明α-D-葡萄糖苷酶和α-D-木糖苷酶活性是由不同的酶引起的。3. 仅含有一种糖苷酶活性的部分纯化酶制剂仅水解相应的糖基氟化物。4. α-D-甘露吡喃糖基氟化物C-1位的构型得到确认，因为它被一种不含可检测到的β-D-甘露糖苷酶活性的α-D-甘露糖苷酶制剂水解。5. 制备邻硝基苯基β-D-甘露吡喃糖苷的尝试仅得到邻硝基苯基α-D-甘露吡喃糖苷。
相似文献
1
The hydrolysis of glycosyl fluorides by glycosidases.糖苷酶催化糖基氟化物的水解反应。
Biochem J. 1967 Nov;105(2):669-72. doi: 10.1042/bj1050669.
2
The hydrolysis of glycosyl fluorides by glycosidases. Determination of the anomeric configuration of the products of glycosidase action.糖苷酶对糖基氟化物的水解作用。糖苷酶作用产物端基构型的测定。
Biochem J. 1971 Jul;123(4):607-11. doi: 10.1042/bj1230607.
3
Enzymic hydrolysis of the carbon-fluorine bond of alpha-D-glucosyl fluoride by rat intestinal mucosa. Localization of intestinal maltase.大鼠肠黏膜对α-D-葡萄糖基氟化物碳氟键的酶促水解。肠麦芽糖酶的定位。
Biochem J. 1967 Jun;103(3):699-704. doi: 10.1042/bj1030699.
4
[Application of glycosyl fluorides in the study on glycosidases].糖基氟化物在糖苷酶研究中的应用
Sheng Wu Gong Cheng Xue Bao. 2006 May;22(3):351-60.
5
2-Deoxy-2-fluoro-D-glycosyl fluorides. A new class of specific mechanism-based glycosidase inhibitors.2-脱氧-2-氟-D-糖基氟化物。一类新型的基于特定机制的糖苷酶抑制剂。
J Biol Chem. 1988 Jun 15;263(17):7929-32.
6
Nitrogen-in-the-ring pyranoses and furanoses: structural basis of inhibition of mammalian glycosidases.环内含氮吡喃糖和呋喃糖：抑制哺乳动物糖苷酶的结构基础
J Med Chem. 1994 Oct 28;37(22):3701-6. doi: 10.1021/jm00048a006.
7
Glycosyl fluorides in enzymatic reactions.酶促反应中的糖基氟化物。
Carbohydr Res. 2000 Jul 10;327(1-2):27-46. doi: 10.1016/s0008-6215(00)00041-0.
8
Protodioscin-glycosidase-1 hydrolyzing 26-O-β-D-glucoside and 3-O-(1 → 4)-α-L-rhamnoside of steroidal saponins from Aspergillus oryzae.米曲霉中甾体皂甙糖苷酶-1 水解 26-O-β-D-葡萄糖苷和 3-O-(1 → 4)-α-L-鼠李糖苷。
Appl Microbiol Biotechnol. 2013 Dec;97(23):10035-43. doi: 10.1007/s00253-013-4791-3. Epub 2013 Mar 7.
9
beta-D-Mannosidase from Helix pomatia.
Carbohydr Res. 1983 Jan 1;111(2):297-310. doi: 10.1016/0008-6215(83)88314-1.
10
3-Methoxy-4-(2-nitrovinyl)phenyl glycosides as potential chromogenic substrates for the assay of glycosidases.
Carbohydr Res. 1986 Feb 1;146(2):241-9. doi: 10.1016/0008-6215(86)85043-1.
引用本文的文献
1
Polarimetry and 13C n.m.r. show that the hydrolyses of beta-D-glucopyranosyl fluoride by beta(1-->3)-glucanases from Phanerochaete chrysosporium and Sporotrichum dimorphosporum have opposite stereochemistries.旋光测定法和碳-13核磁共振显示，来自黄孢原毛平革菌和双形孢帚霉的β(1→3)-葡聚糖酶对β-D-吡喃葡萄糖基氟化物的水解具有相反的立体化学性质。
Biochem J. 1993 Jul 15;293 ( Pt 2)(Pt 2):591-4. doi: 10.1042/bj2930591.
2
Synthesis and biodistribution of 2-deoxy-2-[18F]fluoro-D-glucopyranosyl [18F]fluoride in mice.2-脱氧-2-[¹⁸F]氟-D-吡喃葡萄糖基[¹⁸F]氟化物在小鼠体内的合成与生物分布
Eur J Nucl Med. 1984;9(2):77-80. doi: 10.1007/BF00254441.
3
Structural requirements for active intestinal sugar transport. The involvement of hydrogen bonds at C-1 and C-6 of the sugar.活性肠道糖转运的结构要求。糖的C-1和C-6处氢键的参与。
Biochem J. 1968 Aug;109(1):61-7. doi: 10.1042/bj1090061.
4
The hydrolysis of glycosyl fluorides by glycosidases. Determination of the anomeric configuration of the products of glycosidase action.糖苷酶对糖基氟化物的水解作用。糖苷酶作用产物端基构型的测定。
Biochem J. 1971 Jul;123(4):607-11. doi: 10.1042/bj1230607.
5
-galactosidase-catalysed hydrolysis of -D-galactopyranosyl azide.β-半乳糖苷酶催化的β-D-吡喃半乳糖叠氮化物的水解。
Biochem J. 1971 Dec;125(3):717-9. doi: 10.1042/bj1250717.
6
The beta-galactosidase-catalysed hydrolyses of beta-d-galactopyranosyl pyridium salts. Rate-limiting generation of an enzyme-bound galactopyranosyl cation in a process dependent only on aglycone acidity.β-半乳糖苷酶催化的β-D-吡喃半乳糖基吡啶盐的水解。在仅取决于糖苷配基酸度的过程中，酶结合的吡喃半乳糖基阳离子的限速生成。
Biochem J. 1974 Dec;143(3):751-62. doi: 10.1042/bj1430751.
7
The interaction of 1-fluoro-D-glucopyranosyl fluoride with glucosidases.1-氟-D-吡喃葡萄糖基氟化物与糖苷酶的相互作用。
Biochem J. 1991 Oct 15;279 ( Pt 2)(Pt 2):587-93. doi: 10.1042/bj2790587.
8
Latency of some glycosidases of rat liver lysosomes.大鼠肝脏溶酶体中某些糖苷酶的潜伏期。
Biochem J. 1976 Dec 15;160(3):631-8. doi: 10.1042/bj1600631.
本文引用的文献
1
Inhibition of glycosidases by aldonolactones of corresponding configuration. 3. Inhibitors of beta-D-galactosidase.相应构型的醛糖内酯对糖苷酶的抑制作用。3. β-D-半乳糖苷酶抑制剂。
Biochem J. 1962 Feb;82(2):225-32. doi: 10.1042/bj0820225.
2
Fluoro-D-galactosides as substrates and inducers of the beta-galactosidase of Escherichia coli.氟代-D-半乳糖苷作为大肠杆菌β-半乳糖苷酶的底物和诱导剂
Biochim Biophys Acta. 1961 Mar 18;48:159-63. doi: 10.1016/0006-3002(61)90527-3.
3
The mechanism of the synthesis of enzymes. II. Further observations with particular reference to the linear nature of the time course of enzyme formation.酶合成的机制。II. 特别关于酶形成时间进程的线性性质的进一步观察。
J Gen Physiol. 1953 Nov 20;37(2):271-89. doi: 10.1085/jgp.37.2.271.
4
Enzymic hydrolysis of the carbon-fluorine bond of alpha-D-glucosyl fluoride by rat intestinal mucosa. Localization of intestinal maltase.大鼠肠黏膜对α-D-葡萄糖基氟化物碳氟键的酶促水解。肠麦芽糖酶的定位。
Biochem J. 1967 Jun;103(3):699-704. doi: 10.1042/bj1030699.
5
6
Inhibition of glycosidases by aldonolactones of corresponding configuration. 4. Inhibitors of mannosidase and glucosidase.相应构型的醛糖内酯对糖苷酶的抑制作用。4. 甘露糖苷酶和葡萄糖苷酶的抑制剂。
Biochem J. 1964 May;91(2):378-84. doi: 10.1042/bj0910378.
Zotero 插件