Fructose-1,6-diphosphat | 34693-23-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Fructose-1,6-diphosphat
• 英文别名: fructose 1,6-bisphosphate；[(2S,3S,4S,5R)-2,3,4-trihydroxy-5-(phosphonooxymethyl)oxolan-2-yl]methyl dihydrogen phosphate
• CAS: 34693-23-7
• 化学式: C₆H₁₄O₁₂P₂
• 分子量: 340.117
• InChiKey: RNBGYGVWRKECFJ-ZXXMMSQZSA-N

物化性质

• 碰撞截面：
  168.2 Ų [M+Na]+ [CCS Type: DT, Method: single field calibrated with Agilent tune mix (Agilent)]

计算性质

• 辛醇/水分配系数(LogP)：
  -5.6
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  203
• 氢给体数：
  7
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  Fructose-1,6-diphosphat 在 E_. coli D-glycero-D-manno-heptose-1,7-bisphosphate phosphatase 、 水 、 magnesium chloride 作用下， 生成 果糖-6-磷酸
  参考文献：
  名称：

  Divergence of Biochemical Function in the HAD Superfamily: d-glycero-d-manno-Heptose-1,7-bisphosphate Phosphatase (GmhB)

  摘要：

  D-glycero-D-manno-Heptose-1,7-bisphosphate phosphatase (GmhB) is a member of the histidinol-phosphate phosphatase (HisB) subfamily of the haloalkanoic acid dehalogenase (HAD) enzyme superfamily. GmhB supports two divergent biochemical pathways in bacteria: the D-glycero-D-manno-heptose-1 alpha-GDP pathway (in S-layer glycoprotein biosynthesis) and the L-glycero-D-manno-heptose-1 beta-ADP pathway (in lipid A biosynthesis). Herein, we report the comparative analysis Of Substrate recognition in selected GmhB orthologs. The substrate specificity of the L-glycero-D-manno-heptose-1 beta-ADP pathway GmhB from Escherichia coli K-12 was evaluated using hexose and heptose bisphosphates, histidinol phosphate, and common organophosphate metabolites. Only D-glycero-D-manno-heptose 1 beta,7-bisphosphate (k(cat)/k(m) = 7 x 10(6) M-1 s(-1)) and D-glycero-D-manno-heptose 1 alpha,7-bisphosphate (k(cat)/K-m, = 7 x 10(4) M-1 s(-1)) displayed physiologically significant Substrate activity. P-31 NMR analysis demonstrated that E. coli GmhB selectively removes the C(7) phosphate. Steady-state kinetic inhibition studies showed that D-glycero-D-manno-heptose 1 beta-phosphate (K-is = 60 mu M, and K-ii = 150 mu M) and histidinol phosphate (K-is = 1 mM, and K-ii = 6 mM), while not hydrolyzed, do in fact bind to E. coli GmhB, which leads to the conclusion that nonproductive binding contributes to substrate discrimination. High catalytic efficiency and a narrow substrate range are characteristic of a well-evolved metabolic enzyme, and as such, E. coli GmhB is set apart from most HAD phosphatases (which are typically inefficient and promiscuous). The specialization of the biochemical function of GmhB was examined by measuring the kinetic constants for hydrolysis of the alpha- and beta-anomers of D-glycero-D-manno-heptose 1 beta,7-bisphosphate catalyzed by the GmhB orthologs of the L-glycero-D-manno- 1 beta-ADP pathways operative in Bordetella bronchiseptica and Mesorhizobium and by the GmhB of the D-glycero-D-manno-heptose 1 alpha-GDP pathway operative in Bacteroides thetaiotaomicron. The results show that although each of these representatives possesses physiologically significant catalytic activity toward both anomers, each displays substantial anomeric specificity. Like E. coli GmhB, B. bronchiseptica GmhB and M. loti GmhB prefer the beta-anomer, whereas B. thetaiotaomicron GmhB is selective for the alpha-anomer. By determining the anomeric configuration of the physiological Substrate (D-glycero-D-manno-heptose 1,7- for each of the four GmhB orthologs, we discovered that the anomeric specificity of GmhB correlates with that of the pathway kinase. The conclusion drawn from this finding is that the evolution of the ancestor to GmhB in the HisB subfamily provided for specialization toward two distinct biochemical functions.

  DOI：

  10.1021/bi902018y
• 作为产物：
  描述：

  α-D-fructofuranose 在 rabbit muscle aldolase 、 磷酸丙糖异构酶 、 双甘肽 、 phosphofructokinase 、 α-glycerophosphate dehydrogenase 、 5’-三磷酸腺苷 、 还原型辅酶Ⅰ 、 magnesium chloride 作用下， 生成 Fructose-1,6-diphosphat
  参考文献：
  名称：

  A New Complex of the Ribozyme with Glucose-6-Phosphate Isomerase Activity and the Enzyme Hexokinase in Baker’s Yeast Saccharomyces cerevisiae

  摘要：

  DOI：

  10.1134/s1068162023050084
• 作为试剂：
  描述：

  1,3-dihydroxyacetone phosphate 、 异戊醛 在 Fructose-1,6-diphosphat 作用下， 以37%的产率得到(3S,4R)-1,3,4-trihydroxy-6-methylheptan-2-one
  参考文献：
  名称：

  Amino acid precursors for the detection of transketolase activity in Escherichia coli auxotrophs

  摘要：

  Probes were developed for the in vivo detection of transketolase activity by the use of a complementation assay in Escherichia coli auxotrophs They combine the D-threo ketose moiety recognised by transketolase and the side chain of leucine or methionine. These compounds were donor substrates of yeast transketolase leading to the release of the corresponding alpha-hydroxyaldehydes which could be converted in E. coli by a cascade of reactions into leucine or methionine required for cellular growth. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.04.111

文献信息

• Novel Thiazole Inhibitors of Fructose 1,6-Bishosphatase
  申请人：Dang Qun

  公开号：US20070225259A1

  公开（公告）日：2007-09-27

  Compounds of Formula I, their prodrugs and salts, their preparation and their uses are described.

  公式I的化合物，它们的前药和盐，它们的制备以及它们的用途被描述了。
• Novel Phosphinic Acid-Containing Thyromimetics
  申请人：Erion Mark D.

  公开号：US20090028925A1

  公开（公告）日：2009-01-29

  The present invention relates to compounds of phosphonic acid-containing T3 mimetics and monoesters thereof, stereoisomers, pharmaceutically acceptable salts, co-crystals, and prodrugs thereof and pharmaceutically acceptable salts and co-crystals of the prodrugs, as well as their preparation and uses for preventing and/or treating metabolic diseases such as obesity, NASH, hypercholesterolemia and hyperlipidemia, as well as associated conditions such as atherosclerosis, coronary heart disease, impaired glucose tolerance, metabolic syndrome x and diabetes.

  本发明涉及含有磷酸基T3拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟拟
• Sulfonamides for the Modulation of PKM2
  申请人：Becker Oren M.

  公开号：US20120108631A1

  公开（公告）日：2012-05-03

  The invention relates to sulfonamide compounds and methods for activating PKM2. The compounds and methods are useful in treating or preventing a disease or disorder selected from cancer, cell proliferative disorder, inflammatory disorder, metabolic disorder, and immune system disorder.

  这项发明涉及磺胺类化合物和激活PKM2的方法。这些化合物和方法在治疗或预防癌症、细胞增殖紊乱、炎症性紊乱、代谢紊乱和免疫系统紊乱等疾病或疾病中是有用的。
• Combination of FBPase inhibitors and antidiabetic agents useful for the treatment of diabetes
  申请人：——

  公开号：US20030073728A1

  公开（公告）日：2003-04-17

  A combination therapy of at least one FBPase inhibitor and at least one other antidiabetic agent is disclosed.

  揭示了至少一种FBPase抑制剂和至少一种其他抗糖尿病药物的联合治疗。
• Pyrazolines for the Modulation of PKM2
  申请人：Becker Oren M.

  公开号：US20120302609A1

  公开（公告）日：2012-11-29

  The invention relates to pyrazoline substituted compounds and methods for activating PKM2. The compounds and methods are useful in treating or preventing a disease or disorder selected from cancer, cell proliferative disorder, inflammatory disorder, metabolic disorder, and immune system disorder.

  该发明涉及取代吡唑啉化合物和激活PKM2的方法。这些化合物和方法在治疗或预防癌症、细胞增殖紊乱、炎症性疾病、代谢紊乱和免疫系统紊乱等疾病或疾病中具有用途。