UDP-D-apiose (BioDeep_00000004727)

 

Secondary id: BioDeep_00001869946

human metabolite Endogenous


代谢物信息卡片


[({[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}(hydroxy)phosphoryl)oxy]({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(4-hydroxy-2-oxo-1,2-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy})phosphinic acid

化学式: C14H22N2O16P2 (536.0444552)
中文名称:
谱图信息: 最多检出来源 Macaca mulatta(otcml) 4.55%

分子结构信息

SMILES: C1C(C(C(O1)OP(=O)(O)OP(=O)(O)OCC2C(C(C(O2)N3C=CC(=O)NC3=O)O)O)O)(CO)O
InChI: InChI=1S/C14H22N2O16P2/c17-4-14(23)5-28-12(10(14)21)31-34(26,27)32-33(24,25)29-3-6-8(19)9(20)11(30-6)16-2-1-7(18)15-13(16)22/h1-2,6,8-12,17,19-21,23H,3-5H2,(H,24,25)(H,26,27)(H,15,18,22)/t6-,8-,9-,10+,11-,12+,14-/m1/s1

描述信息

D-apiose is a plant-specific branched-chain monosaccharide found in rhamnogalacturonan II (RG-II), apiogalacturonan, and several apioglycosides. Within RG-II, d-apiose serves as the binding site for borate, which leads to the formation of cross-links within the wall. Biochemical studies in duckweed and parsley have established that uridine 5-diphospho-d-apiose (UDP-d-apiose) is formed from UDP-d-glucuronate by decarboxylation and re-arrangement of the carbon skeleton, leading to ring contraction and branch formation. The enzyme catalyzing this reaction also forms UDP-d-xylose by decarboxylation of UDP-d-glucuronate, and has therefore been named UDP-d-apiose/UDP-d-xylose synthase. (PMID: 12969423) [HMDB]
D-Apiose is a plant-specific branched-chain monosaccharide found in rhamnogalacturonan II (RG-II), apiogalacturonan, and several apioglycosides. Within RG-II, D-apiose serves as the binding site for borate, which leads to the formation of cross-links within the wall. Biochemical studies in duckweed and parsley have established that uridine 5-diphospho-D-apiose (UDP-D-apiose) is formed from UDP-D-glucuronate by decarboxylation and re-arrangement of the carbon skeleton, leading to ring contraction and branch formation. The enzyme catalyzing this reaction also forms UDP-D-xylose by decarboxylation of UDP-D-glucuronate, and has therefore been named UDP-D-apiose/UDP-D-xylose synthase (PMID: 12969423).

同义名列表

6 个代谢物同义名

[({[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}(hydroxy)phosphoryl)oxy]({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(4-hydroxy-2-oxo-1,2-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy})phosphinic acid; [({[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}(hydroxy)phosphoryl)oxy]({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(4-hydroxy-2-oxo-1,2-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy})phosphinate; {[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy(hydroxy)phosphoryl}oxy([(2R,3S,4R,5R)-3,4-dihydroxy-5-(4-hydroxy-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy)phosphinic acid; Uridine 5-(alpha-D-apio-D-furanosyl pyrophosphate); UDP-D-apiose; UDP-Apiose



数据库引用编号

15 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

PlantCyc(0)

代谢反应

222 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(222)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

1 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：

  • PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。



文献列表

  • Xianhai Zhao, Berit Ebert, Baocai Zhang, Huabin Liu, Yutao Zhang, Wei Zeng, Carsten Rautengarten, Huiling Li, Xiaoyang Chen, Antony Bacic, Guodong Wang, Shuzhen Men, Yihua Zhou, Joshua L Heazlewood, Ai-Min Wu. UDP-Api/UDP-Xyl synthases affect plant development by controlling the content of UDP-Api to regulate the RG-II-borate complex. The Plant journal : for cell and molecular biology. 2020 09; 104(1):252-267. doi: 10.1111/tpj.14921. [PMID: 32662159]
  • James Amor Smith, Maor Bar-Peled. Synthesis of UDP-apiose in Bacteria: The marine phototroph Geminicoccus roseus and the plant pathogen Xanthomonas pisi. PloS one. 2017; 12(9):e0184953. doi: 10.1371/journal.pone.0184953. [PMID: 28931093]
  • Sen Yin, Jian-Qiang Kong. Transcriptome-guided gene isolation and functional characterization of UDP-xylose synthase and UDP-D-apiose/UDP-D-xylose synthase families from Ornithogalum caudatum Ait. Plant cell reports. 2016 Nov; 35(11):2403-2421. doi: 10.1007/s00299-016-2044-5. [PMID: 27591771]
  • James Smith, Yiwen Yang, Shahar Levy, Oluwatoyin Oluwayemi Adelusi, Michael G Hahn, Malcolm A O'Neill, Maor Bar-Peled. Functional Characterization of UDP-apiose Synthases from Bryophytes and Green Algae Provides Insight into the Appearance of Apiose-containing Glycans during Plant Evolution. The Journal of biological chemistry. 2016 Oct; 291(41):21434-21447. doi: 10.1074/jbc.m116.749069. [PMID: 27551039]
  • Joon-Woo Ahn, Rajeev Verma, Moonil Kim, Jae-Yong Lee, Yu-Kyung Kim, Jae-Wook Bang, Wolf-Dieter Reiter, Hyun-Sook Pai. Depletion of UDP-D-apiose/UDP-D-xylose synthases results in rhamnogalacturonan-II deficiency, cell wall thickening, and cell death in higher plants. The Journal of biological chemistry. 2006 May; 281(19):13708-13716. doi: 10.1074/jbc.m512403200. [PMID: 16549428]