9-Ribosyl-trans-zeatin 5'-triphosphate(4-)

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷酸
• 英文名称: 9-Ribosyl-trans-zeatin 5'-triphosphate(4-)
• 英文别名: [[[(2R,3S,4R,5R)-3,4-dihydroxy-5-[6-[[(E)-4-hydroxy-3-methylbut-2-enyl]amino]purin-9-yl]oxolan-2-yl]methoxy-oxidophosphoryl]oxy-oxidophosphoryl] phosphate
• 化学式: C15H20N5O14P3-4
• 分子量: 587.27
• InChiKey: AOFQQLZNDSBFLN-HNNGNKQASA-J

计算性质

• 辛醇/水分配系数(LogP)：
  -5.1
• 重原子数：
  37
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  297
• 氢给体数：
  4
• 氢受体数：
  18

反应信息

• 作为产物：
  描述：

  氢(+1)阳离子 、 N(6)-(dimethylallyl)adenosine 5'-triphosphate(4-) 、 NADPH(4-) 、 氧气 生成 9-Ribosyl-trans-zeatin 5'-triphosphate(4-) 、 水 、 NADP⁺
  参考文献：
  名称：

  Arabidopsis CYP735A1 and CYP735A2 Encode Cytokinin Hydroxylases That Catalyze the Biosynthesis of trans-Zeatin

  摘要：

  Cytokinins (CKs), a group of phytohormones, are adenine derivatives that carry either an isoprene-derived or an aromatic side chain at the N-6 terminus. trans-Zeatin (tZ), an isoprenoid CK, is assumed to play a central physiological role because of its general occurrence and high activity in bioassays. Although hydroxylation of isopentenyladenine-type CKs is a key step of tZ biosynthesis, the catalyzing enzyme has not been characterized yet. Here we demonstrate that CYP735A1 and CYP735A2 are cytochrome P450 monooxygenases (P450s) that catalyze the biosynthesis of tZ. We identified the genes from Arabidopsis using an adenosine phosphate-isopentenyltransferase (AtIPT4)/P450 co-expression system in yeast. Co-expression of AtIPT4 and CYP735A enabled yeast to excrete tZ and the nucleosides to the culture medium. In vitro, both CYP735As preferentially utilized isopentenyladenine nucleotides rather than the nucleoside and free base forms and produced tZ nucleotides but not the cis-isomer. The expression of CYP735A1 and CYP735A2 was differentially regulated in terms of organ specificity and response to CK. Root-specific induction of CYP735A2 expression by CK suggests that the trans-hydroxylation is involved in the regulation of CK metabolism and signaling in roots.

  DOI：

  10.1074/jbc.m406337200

文献信息

• Arabidopsis CYP735A1 and CYP735A2 Encode Cytokinin Hydroxylases That Catalyze the Biosynthesis of trans-Zeatin
  作者：Kentaro Takei、Tomoyuki Yamaya、Hitoshi Sakakibara

  DOI：10.1074/jbc.m406337200

  日期：2004.10

  Cytokinins (CKs), a group of phytohormones, are adenine derivatives that carry either an isoprene-derived or an aromatic side chain at the N-6 terminus. trans-Zeatin (tZ), an isoprenoid CK, is assumed to play a central physiological role because of its general occurrence and high activity in bioassays. Although hydroxylation of isopentenyladenine-type CKs is a key step of tZ biosynthesis, the catalyzing enzyme has not been characterized yet. Here we demonstrate that CYP735A1 and CYP735A2 are cytochrome P450 monooxygenases (P450s) that catalyze the biosynthesis of tZ. We identified the genes from Arabidopsis using an adenosine phosphate-isopentenyltransferase (AtIPT4)/P450 co-expression system in yeast. Co-expression of AtIPT4 and CYP735A enabled yeast to excrete tZ and the nucleosides to the culture medium. In vitro, both CYP735As preferentially utilized isopentenyladenine nucleotides rather than the nucleoside and free base forms and produced tZ nucleotides but not the cis-isomer. The expression of CYP735A1 and CYP735A2 was differentially regulated in terms of organ specificity and response to CK. Root-specific induction of CYP735A2 expression by CK suggests that the trans-hydroxylation is involved in the regulation of CK metabolism and signaling in roots.