9-[5'-脱氧-5'-(甲硫基)-β-D-木呋喃糖基]腺嘌呤的生物合成与代谢，一种新型甲硫基腺苷天然类似物
Biosynthesis and metabolism of 9-[5'-deoxy-5'-(methylthio)-beta-D-xylofuranosyl]adenine, a novel natural analogue of methylthioadenosine.
作者信息
Porcelli M, Cacciapuoti G, Cimino G, Gavagnin M, Sodano G, Zappia V
机构信息
Istituto di Biochimica delle Macromolecole, I Facoltà di Medicina e Chirurgia, Università di Napoli, Italy.
出版信息
Biochem J. 1989 Nov 1;263(3):635-40. doi: 10.1042/bj2630635.
Abstract
The biosynthesis of 9-[5'-deoxy-5'-(methylthio)-beta-D-xylofuranosyl]adenine (xylosyl-MTA), a naturally occurring analogue of 5'-deoxy-5'-methylthioadenosine (MTA) recently characterized, was studied in the nudibranch mollusc Doris verrucosa. Experiments performed in vivo with putative labelled precursors such as [8-14C]adenine, [Me-14C]methionine and [Me-14C]MTA indicate that xylosyl-MTA originates from MTA. Experiments with MTA double-labelled at critical positions are consistent with a 3'-isomerization of the nucleoside through the formation of a 3'-oxo intermediate. In addition, experiments with the newly synthesized [3'-3H]xylosyl-MTA are indicative for a very low turnover rate of this molecule, which therefore accumulates in the mollusc.
摘要
9-[5'-脱氧-5'-(甲硫基)-β-D-木糖呋喃糖基]腺嘌呤（木糖基-MTA）是最近鉴定出的5'-脱氧-5'-甲硫基腺苷（MTA）的天然类似物，其生物合成在裸鳃亚目软体动物疣背海牛中进行了研究。使用[8-14C]腺嘌呤、[甲基-14C]甲硫氨酸和[甲基-14C]MTA等假定标记前体进行的体内实验表明，木糖基-MTA源自MTA。在关键位置进行双标记的MTA实验与通过形成3'-氧代中间体使核苷发生3'-异构化一致。此外，使用新合成的[3'-3H]木糖基-MTA进行的实验表明该分子的周转速率非常低，因此在软体动物中积累。
相似文献
1
Biosynthesis and metabolism of 9-[5'-deoxy-5'-(methylthio)-beta-D-xylofuranosyl]adenine, a novel natural analogue of methylthioadenosine.9-[5'-脱氧-5'-(甲硫基)-β-D-木呋喃糖基]腺嘌呤的生物合成与代谢，一种新型甲硫基腺苷天然类似物
Biochem J. 1989 Nov 1;263(3):635-40. doi: 10.1042/bj2630635.
2
High-performance liquid chromatographic determination of a naturally occurring xylosyl thioether, 9-[5'-deoxy-5'(methylthio)-beta-D-xylofuranosyl]adenine.高效液相色谱法测定一种天然存在的木糖基硫醚，9-[5'-脱氧-5'(甲硫基)-β-D-木糖呋喃糖基]腺嘌呤。
J Chromatogr. 1988 May 25;440:151-5. doi: 10.1016/s0021-9673(00)94519-9.
3
5'-deoxy-5'-methylthioadenosine phosphorylase--IV. Biological activity of 2-fluoroadenine-substituted 5'-deoxy-5'-methylthioadenosine analogs.5'-脱氧-5'-甲硫基腺苷磷酸化酶——IV. 2-氟腺嘌呤取代的5'-脱氧-5'-甲硫基腺苷类似物的生物活性
Biochem Pharmacol. 1987 Jun 15;36(12):1881-93. doi: 10.1016/0006-2952(87)90484-9.
4
5'-deoxy-5'-methylthioadenosine phosphorylase--II. Role of the enzyme in the metabolism and antineoplastic action of adenine-substituted analogs of 5'-deoxy-5'-methylthioadenosine.5'-脱氧-5'-甲硫基腺苷磷酸化酶——II. 该酶在5'-脱氧-5'-甲硫基腺苷腺嘌呤取代类似物的代谢及抗肿瘤作用中的角色
Biochem Pharmacol. 1983 Jun 15;32(12):1907-16. doi: 10.1016/0006-2952(83)90057-6.
5
Androgenic regulation of 5'-deoxy-5'-methylthioadenosine concentrations and methylthioadenosine phosphorylase activity in relation to polyamine metabolism of rat prostate.雄激素对大鼠前列腺5'-脱氧-5'-甲硫腺苷浓度及甲硫腺苷磷酸化酶活性的调节及其与多胺代谢的关系
Biochem Biophys Res Commun. 1980 Aug 29;95(4):1861-8. doi: 10.1016/s0006-291x(80)80116-1.
6
Targeting 5'-deoxy-5'-(methylthio)adenosine phosphorylase by 5'-haloalkyl analogues of 5'-deoxy-5'-(methylthio)adenosine.通过5'-脱氧-5'-(甲硫基)腺苷的5'-卤代烷基类似物靶向5'-脱氧-5'-(甲硫基)腺苷磷酸化酶。
J Med Chem. 1991 Aug;34(8):2600-6. doi: 10.1021/jm00112a039.
7
Antimicrobial and antiviral activity of xylosyl-methylthio-adenosine, a naturally occurring analogue of methylthio-adenosine from Doris verrucosa.来自疣背海牛的天然存在的甲硫腺苷类似物木糖基甲硫腺苷的抗菌和抗病毒活性。
Experientia. 1991 Dec 1;47(11-12):1228-9. doi: 10.1007/BF01918391.
8
Salvage of 5'-deoxy-methylthioadenosine into purines and methionine by lymphoid cells and inhibition of cell proliferation.淋巴细胞将5'-脱氧甲基硫代腺苷挽救为嘌呤和蛋氨酸并抑制细胞增殖。
Biochim Biophys Acta. 1984 Feb 17;803(1-2):7-10. doi: 10.1016/0167-4889(84)90048-x.
9
The metabolism of 5'-methylthioadenosine and 5-methylthioribose 1-phosphate in Saccharomyces cerevisiae.酿酒酵母中5'-甲硫基腺苷和5-甲硫基核糖1-磷酸的代谢
J Gen Microbiol. 1985 Sep;131(9):2153-64. doi: 10.1099/00221287-131-9-2153.
10
5'-Methylthioadenosine (MTA) phosphorylase from promastigotes of Leishmania donovani.来自杜氏利什曼原虫前鞭毛体的5'-甲硫腺苷（MTA）磷酸化酶。
Adv Exp Med Biol. 1986;195 Pt B:559-63. doi: 10.1007/978-1-4684-1248-2_87.
引用本文的文献
1
Biosynthesis of the Methylthioxylose Capping Motif of Lipoarabinomannan in Mycobacterium tuberculosis.结核分枝杆菌中脂阿拉伯甘露聚糖甲基硫代木糖封端基序的生物合成
ACS Chem Biol. 2017 Mar 17;12(3):682-691. doi: 10.1021/acschembio.6b01071. Epub 2017 Jan 20.
2
Antimicrobial and antiviral activity of xylosyl-methylthio-adenosine, a naturally occurring analogue of methylthio-adenosine from Doris verrucosa.来自疣背海牛的天然存在的甲硫腺苷类似物木糖基甲硫腺苷的抗菌和抗病毒活性。
Experientia. 1991 Dec 1;47(11-12):1228-9. doi: 10.1007/BF01918391.
本文引用的文献
1
OBSERVATIONS ON THE METABOLISM OF 5'-METHYLTHIOADENOSINE.关于5'-甲硫腺苷代谢的观察
Arch Biochem Biophys. 1964 Jul 20;106:95-100. doi: 10.1016/0003-9861(64)90161-4.
2
The formation of S-adenosylmethionine in yeast.酵母中S-腺苷甲硫氨酸的形成。
J Biol Chem. 1957 Dec;229(2):1037-50.
3
Decarboxylated S-adenosylmethionine in mammalian cells.哺乳动物细胞中的脱羧S-腺苷甲硫氨酸。
J Biol Chem. 1980 Jul 25;255(14):6675-8.
4
High-performance liquid chromatographic separation of natural adenosyl-sulphur compounds.天然腺苷硫化合物的高效液相色谱分离
J Chromatogr. 1980 Mar 7;189(3):399-405. doi: 10.1016/s0021-9673(00)80319-2.
5
Effects of inhibitors of spermidine and spermine synthesis on polyamine concentrations and growth of transformed mouse fibroblasts.亚精胺和精胺合成抑制剂对转化小鼠成纤维细胞多胺浓度及生长的影响
Biochem J. 1981 Jan 15;194(1):79-89. doi: 10.1042/bj1940079.
6
High-performance liquid chromatographic analysis of 5'-methylthioadenosine in rat tissues.大鼠组织中5'-甲硫腺苷的高效液相色谱分析
J Chromatogr. 1981 Nov 13;226(1):243-9. doi: 10.1016/s0378-4347(00)84229-2.
7
Trends in the biochemical pharmacology of 5'-deoxy-5'-methylthioadenosine.5'-脱氧-5'-甲硫基腺苷的生化药理学研究趋势
Biochem Pharmacol. 1982 Feb 1;31(3):277-88. doi: 10.1016/0006-2952(82)90171-x.
8
High-performance liquid chromatographic analysis of adenosyl-sulfur compounds related to polyamine biosynthesis.与多胺生物合成相关的腺苷硫化合物的高效液相色谱分析
Methods Enzymol. 1983;94:57-66. doi: 10.1016/s0076-6879(83)94010-7.
9
Inhibition of dimethyl sulfoxide-induced differentiation of Friend erythroleukemic cells by 5'-methylthioadenosine.5'-甲硫腺苷对二甲基亚砜诱导的弗氏红白血病细胞分化的抑制作用。
Cancer Res. 1984 Sep;44(9):4096-103.
10
Rapid assays for putrescine aminopropyltransferase (spermidine synthase) and spermidine aminopropyltransferase (spermine synthase).腐胺氨基丙基转移酶（亚精胺合酶）和亚精胺氨基丙基转移酶（精胺合酶）的快速检测方法。
Methods Enzymol. 1983;94:257-60. doi: 10.1016/s0076-6879(83)94044-2.
Zotero 插件