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1
Synthesis, characterization and properties of uridine 5'-( -D-apio-D-furanosyl pyrophosphate).尿苷5'-(-D-阿卓-D-呋喃糖基焦磷酸)的合成、表征及性质
Biochem J. 1973 Jun;133(2):227-41. doi: 10.1042/bj1330227.
2
Real-time NMR monitoring of intermediates and labile products of the bifunctional enzyme UDP-apiose/UDP-xylose synthase.双功能酶UDP-芹糖/UDP-木糖合酶中间体和不稳定产物的实时核磁共振监测
Carbohydr Res. 2009 Jun 12;344(9):1072-8. doi: 10.1016/j.carres.2009.03.026. Epub 2009 Mar 27.
3
Conversion of UDP-D-glucuronic acid to UDP-D-apiose and UDP-D-xylose by an enzyme isolated from Lemna minor.从小浮萍中分离出的一种酶将UDP-D-葡萄糖醛酸转化为UDP-D-芹糖和UDP-D-木糖。
Biochim Biophys Acta. 1974 Sep 11;364(1):159-72. doi: 10.1016/0005-2744(74)90143-0.
4
Purification and properties of an enzyme from cell suspension cultures of parsley catalyzing the synthesis of UDP-apiose and UDP-D-xylose from UDP-D-glucuronic acid.从欧芹细胞悬浮培养物中纯化出一种酶及其性质,该酶催化从UDP-D-葡萄糖醛酸合成UDP-芹糖和UDP-D-木糖。
Biochim Biophys Acta. 1972 Jan 20;258(1):310-8. doi: 10.1016/0005-2744(72)90988-6.
5
Transfer of apiose from UDP-apiose to 7-O-(beta-D-glucosyl)-apigenin and 7-O-(beta-D-glucosyl)-chrysoeriol with an enzyme preparation from parsley.使用来自欧芹的酶制剂将芹糖从尿苷二磷酸芹糖转移至7 - O -(β - D - 葡萄糖基)芹菜素和7 - O -(β - D - 葡萄糖基) Chrysoeriol。
FEBS Lett. 1970 Apr 2;7(2):164-166. doi: 10.1016/0014-5793(70)80146-6.
6
Practical preparation of UDP-apiose and its applications for studying apiosyltransferase.UDP-apiose 的实际制备及其在研究 apiosyltransferase 中的应用。
Carbohydr Res. 2019 May 15;477:20-25. doi: 10.1016/j.carres.2019.03.011. Epub 2019 Mar 23.
7
The biosynthesis of the branched-chain sugar d-apiose in plants: functional cloning and characterization of a UDP-d-apiose/UDP-d-xylose synthase from Arabidopsis.植物中支链糖D-阿洛糖的生物合成:来自拟南芥的UDP-D-阿洛糖/UDP-D-木糖合酶的功能克隆与特性分析
Plant J. 2003 Sep;35(6):693-703. doi: 10.1046/j.1365-313x.2003.01841.x.
8
Biosynthesis of D-apiose. V. NAD+-dependent biosynthesis of UDP-apiose and UDP-xylose from UDP-D-glucuronic acid with an enzyme preparation from Lemna minor L.D-阿糖的生物合成。V. 利用浮萍(Lemna minor L.)的酶制剂从UDP-D-葡萄糖醛酸通过NAD⁺依赖性生物合成UDP-阿糖和UDP-木糖
Biochim Biophys Acta. 1970 May 12;208(2):173-80. doi: 10.1016/0304-4165(70)90235-7.
9
Analysis of UDP-D-apiose/UDP-D-xylose synthase-catalyzed conversion of UDP-D-apiose phosphonate to UDP-D-xylose phosphonate: implications for a retroaldol-aldol mechanism.分析 UDP-D-岩藻糖/ UDP-D-木糖合酶催化 UDP-D-岩藻糖磷酸酯向 UDP-D-木糖磷酸酯的转化:对 retroaldol-aldol 机制的启示。
J Am Chem Soc. 2012 Aug 29;134(34):13946-9. doi: 10.1021/ja305322x. Epub 2012 Aug 15.
10
A fluoro analogue of UDP-α-D-glucuronic acid is an inhibitor of UDP-α-D-apiose/UDP-α-D-xylose synthase.尿苷二磷酸-α-D-葡萄糖醛酸的氟代类似物是 UDP-α-D-艾杜糖醛酸/ UDP-α-D-木糖合酶的抑制剂。
Chem Commun (Camb). 2011 Sep 28;47(36):10130-2. doi: 10.1039/c1cc13140k. Epub 2011 Aug 9.

引用本文的文献

1
Analysis of UDP-D-apiose/UDP-D-xylose synthase-catalyzed conversion of UDP-D-apiose phosphonate to UDP-D-xylose phosphonate: implications for a retroaldol-aldol mechanism.分析 UDP-D-岩藻糖/ UDP-D-木糖合酶催化 UDP-D-岩藻糖磷酸酯向 UDP-D-木糖磷酸酯的转化:对 retroaldol-aldol 机制的启示。
J Am Chem Soc. 2012 Aug 29;134(34):13946-9. doi: 10.1021/ja305322x. Epub 2012 Aug 15.
2
Developmental Control of Apiogalacturonan Biosynthesis and UDP-Apiose Production in a Duckweed.浮萍中果胶寡糖生物合成和 UDP-阿比糖产生的发育调控
Plant Physiol. 1989 Jul;90(3):972-6. doi: 10.1104/pp.90.3.972.
3
Molecular genetics of nucleotide sugar interconversion pathways in plants.植物中核苷酸糖相互转化途径的分子遗传学
Plant Mol Biol. 2001 Sep;47(1-2):95-113.
4
Biosynthetic origin of mycobacterial cell wall arabinosyl residues.分枝杆菌细胞壁阿拉伯糖基残基的生物合成起源。
J Bacteriol. 1995 Dec;177(24):7125-30. doi: 10.1128/jb.177.24.7125-7130.1995.

本文引用的文献

1
The chromatographic identification of some biologically important phosphate esters.某些具有重要生物学意义的磷酸酯的色谱鉴定
J Biol Chem. 1951 Nov;193(1):405-10.
2
BIOSYNTHESIS OF SACCHARIDES FROM GLYCOPYRANOSYL ESTERS OF NUCLEOTIDES ("SUGAR NUCLEOTIDES").由核苷酸的吡喃糖基酯(“糖核苷酸”)合成糖类
Adv Carbohydr Chem. 1963;18:309-56.
3
Structural chemistry of the hemicelluloses.半纤维素的结构化学
Adv Carbohydr Chem. 1959;14:429-68. doi: 10.1016/s0096-5332(08)60228-3.
4
Phosphorus assay in column chromatography.柱色谱法中的磷测定
J Biol Chem. 1959 Mar;234(3):466-8.
5
Studies on uridine-diphosphate-glucose.尿苷二磷酸葡萄糖的研究。
Biochem J. 1952 Jun;51(3):426-30. doi: 10.1042/bj0510426.
6
Enzymic synthesis of uridine diphosphoglucose-14-C.尿苷二磷酸葡萄糖-14-C的酶促合成
Anal Biochem. 1966 Apr;15(1):150-3. doi: 10.1016/0003-2697(66)90257-0.
7
Ion-exchange paper chromatography of nucleoside diphosphate sugars and related nucleotides.核苷二磷酸糖及相关核苷酸的离子交换纸色谱法
Anal Biochem. 1965 Jun;11(3):497-509. doi: 10.1016/0003-2697(65)90068-0.
8
Biosynthesis of D-apiose in a cell-free system from Lemna minor L.在来自浮萍(Lemna minor L.)的无细胞体系中D-阿洛糖的生物合成
J Biol Chem. 1969 Mar 10;244(5):1382-5.
9
Biosynthesis of D-apiose. IV. Formation of UDP-apiose from UDP-D-glucuronic acid in cell-free extracts of parsley (Apium petroselinum L.) and Lemna minor.D-阿比糖的生物合成。IV. 在欧芹(Apium petroselinum L.)和浮萍(Lemna minor)的无细胞提取物中由UDP-D-葡萄糖醛酸形成UDP-阿比糖。
Biochim Biophys Acta. 1968 Oct 15;165(3):550-2. doi: 10.1016/0304-4165(68)90239-0.
10
The synthesis of isomers of D-apiofuranosyl 1-phosphate.D-阿吡呋喃糖基1-磷酸酯异构体的合成。
J Biol Chem. 1970 Nov 25;245(22):6113-24.

尿苷5'-(-D-阿卓-D-呋喃糖基焦磷酸)的合成、表征及性质

Synthesis, characterization and properties of uridine 5'-( -D-apio-D-furanosyl pyrophosphate).

作者信息

Kindel P K, Watson R R

出版信息

Biochem J. 1973 Jun;133(2):227-41. doi: 10.1042/bj1330227.

DOI:10.1042/bj1330227
PMID:4723773
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC1177691/
Abstract
  1. A method was developed for synthesizing UDP-apiose [uridine 5'-(alpha-d-apio-d-furanosyl pyrophosphate)] from UDP-glucuronic acid [uridine 5'-(alpha-d-glucopyranosyluronic acid pyrophosphate)] in 62% yield with the enzyme UDP-glucuronic acid cyclase. 2. UDP-apiose had the same mobility as uridine 5'-(alpha-d-xylopyranosyl pyrophosphate) when chromatographed on paper and when subjected to paper electrophoresis at pH5.8. When [(3)H]UDP-[U-(14)C]glucuronic acid was used as the substrate for UDP-glucuronic acid cyclase, the (3)H/(14)C ratio in the reaction product was that expected if d-apiose remained attached to the uridine. In separate experiments doubly labelled reaction product was: (a) hydrolysed at pH2 and 100 degrees C for 15min; (b) degraded at pH8.0 and 100 degrees C for 3min; (c) used as a substrate in the enzymic synthesis of [(14)C]apiin. In each type of experiment the reaction products were isolated and identified and were found to be those expected if [(3)H]UDP-[U-(14)C]apiose was the starting compound. 3. Chemical characterization established that the product containing d-[U-(14)C]apiose and phosphate formed on alkaline degradation of UDP-[U-(14)C]apiose was alpha-d-[U-(14)C]apio-d-furanosyl 1:2-cyclic phosphate. 4. Chemical characterization also established that the product containing d-[U-(14)C]apiose and phosphate formed on acid hydrolysis of alpha-d-[U-(14)C]apio-d-furanosyl 1:2-cyclic phosphate was d-[U-(14)C]apiose 2-phosphate. 5. The half-life periods for the degradation of UDP-[U-(14)C]apiose to alpha-d-[U-(14)C]apio-d-furanosyl 1:2-cyclic phosphate and UMP at pH8.0 and 80 degrees C, at pH8.0 and 25 degrees C and at pH8.0 and 4 degrees C were 31.6s, 97.2min and 16.5h respectively. The half-life period for the hydrolysis of UDP-[U-(14)C]-apiose to d-[U-(14)C]apiose and UDP at pH3.0 and 40 degrees C was 4.67min. After 20 days at pH6.2-6.6 and 4 degrees C, 17% of the starting UDP-[U-(14)C]apiose was degraded to alpha-d-[U-(14)C]apio-d-furanosyl 1:2-cyclic phosphate and UMP and 23% was hydrolysed to d-[U-(14)C]apiose and UDP. After 120 days at pH6.4 and -20 degrees C 2% of the starting UDP-[U-(14)C]apiose was degraded and 4% was hydrolysed.
摘要
  1. 开发了一种方法,可利用UDP - 葡萄糖醛酸环化酶从UDP - 葡萄糖醛酸[尿苷5' -(α - D - 吡喃葡萄糖醛酸焦磷酸)]合成UDP - 阿比糖[尿苷5' -(α - D - 阿比 - D - 呋喃糖基焦磷酸)],产率为62%。2. UDP - 阿比糖在纸上色谱分析以及在pH5.8条件下进行纸电泳时,其迁移率与尿苷5' -(α - D - 吡喃木糖基焦磷酸)相同。当[(³H)UDP - [U - (¹⁴C)]葡萄糖醛酸用作UDP - 葡萄糖醛酸环化酶的底物时,反应产物中的³H/¹⁴C比值符合如果D - 阿比糖仍与尿苷相连时的预期值。在单独的实验中,对双重标记的反应产物进行了如下处理:(a) 在pH2和100℃下水解15分钟;(b) 在pH8.0和100℃下降解3分钟;(c) 用作[(¹⁴C)]芹菜素酶促合成的底物。在每种类型的实验中,对反应产物进行了分离和鉴定,发现其为预期的产物,前提是[(³H)UDP - [U - (¹⁴C)]阿比糖是起始化合物。3. 化学表征确定,UDP - [U - (¹⁴C)]阿比糖碱性降解后形成的含有D - [U - (¹⁴C)]阿比糖和磷酸盐的产物是α - D - [U - (¹⁴C)]阿比 - D - 呋喃糖基1:2 - 环磷酸酯。4. 化学表征还确定,α - D - [U - (¹⁴C)]阿比 - D - 呋喃糖基1:2 - 环磷酸酯酸水解后形成的含有D - [U - (¹⁴C)]阿比糖和磷酸盐的产物是D - [U - (¹⁴C)]阿比糖2 - 磷酸酯。5. 在pH8.0和80℃、pH8.0和25℃以及pH8.0和4℃条件下,UDP - [U - (¹⁴C)]阿比糖降解为α - D - [U - (¹⁴C)]阿比 - D - 呋喃糖基1:2 - 环磷酸酯和UMP的半衰期分别为31.6秒、97.2分钟和16.5小时。在pH3.0和40℃条件下,UDP - [U - (¹⁴C)] - 阿比糖水解为D - [U - (¹⁴C)]阿比糖和UDP的半衰期为4.67分钟。在pH6.2 - 6.6和4℃条件下放置20天后,起始的UDP - [U - (¹⁴C)]阿比糖中有17%降解为α - D - [U - (¹⁴C)]阿比 - D - 呋喃糖基1:2 - 环磷酸酯和UMP,23%水解为D - [U - (¹⁴C)]阿比糖和UDP。在pH6.4和 - 20℃条件下放置120天后,起始的UDP - [U - (¹⁴C)]阿比糖中有2%降解,4%水解。