3-amino-3-deoxy-D-glucopyranose-6-phosphate

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-amino-3-deoxy-D-glucopyranose-6-phosphate
• 英文别名: 3-amino-3-deoxy-D-glucose 6-phosphate；kanosamine 6-phosphate；[(2R,3S,4S,5R)-4-amino-3,5,6-trihydroxyoxan-2-yl]methyl dihydrogen phosphate
• 化学式: C₆H₁₄NO₈P
• 分子量: 259.153
• InChiKey: FNLHPZUNSZDBLN-CBPJZXOFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -6.8
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  163
• 氢给体数：
  6
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  3-amino-3-deoxy-D-glucopyranose-6-phosphate 在 2-deoxy-scyllo-inosose synthase from Escherichia coli 、 nicotinamide adenine dinucleotide 作用下， 以 various solvent(s) 为溶剂， 反应 0.5h， 生成 2-deoxy-5-amino-scyllo-inosose
  参考文献：
  名称：

  特定氢键供体-受体相互作用对于2-脱氧-鞘氨醇合酶催化的关键碳环形成反应在含2-脱氧链胺胺的氨基环糖醇抗生素生物合成中的重要性。

  摘要：

  在临床上重要的氨基环醇抗生素的2-deoxystreptamine糖苷生物合成中的关键酶是2-deoxy-scyllo-inosose合酶（DOIS），它将普遍存在的D-葡萄糖6-磷酸酯（G-6-P）转化为特定的碳环2-脱氧鞘氨醇。在底物的所有氧化碳中，C-1，-4，-5和-6直接参与化学转化。为了深入了解C-2和C-3羟基，2-脱氧-2-氟，3-脱氧-3-氟，2-氨基-2-脱氧和3-氨基-3的作用-脱氧D-葡萄糖6-磷酸酯（2-FG-6-P，3-FG-6-P，2-NH（2）-G-6-P和3-NH（2）-G-6 -P）分别作为探针进行DOIS反应，因为氟取代基通常充当氢键受体，而生理上衍生自氨基的铵官能团作为氢键供体。在测试的那些当中，2-FG-6-P和3-NH（2）-G-6-P被DOIS用作底物，并分别转化为相应的脱氧氟-和氨基脱氧-鞘氨醇。相反，3-FG-6-P和2-NH（2）-G-6

  DOI：

  10.1021/jo011107n
• 作为产物：
  描述：

  尿苷(5')二氢二磷酰(1)-alpha-D-葡萄糖 在 sodium hydroxide 、 hexokinase L-谷氨酰胺 、 A_. mediterranei cell-free extract 、 β-烟酰胺腺嘌呤二核苷酸 、 5’-三磷酸腺苷 、 柠檬酸 、 magnesium chloride 作用下， 反应 36.0h， 生成 3-amino-3-deoxy-D-glucopyranose-6-phosphate
  参考文献：
  名称：

  Kanosamine 生物合成：Aminoshikimate 途径的氮原子的可能来源

  摘要：

  掺入氨基莽草酸酯途径的氮原子的生物合成来源一直是一个问题。3-氨基-3-脱氧-D-果糖 6-磷酸先前已被证明是 4-氨基-3,4-二脱氧-D-阿拉伯-庚糖酸 7-磷酸和 3-氨基-5-羟基苯甲酸的前体通过推断的 1-deoxy-1-imino-D-erythrose 4-phosphate 中间体在 Amycolatopsis mediterranei 无细胞提取物中产生酸。这项调查研究了天然产物卡诺胺可能是 3-amino-3-deoxy-D-fructose 6-phosphate 的前体的可能性。卡诺胺 6-磷酸是通过化学酶促途径合成的，并与 D-核糖 5-磷酸和磷酸烯醇丙酮酸一起在无细胞裂解物中孵育。4-氨基-3的形成，观察到4-双脱氧-D-阿拉伯-庚酮糖酸7-磷酸和3-氨基-5-羟基苯甲酸。随后在 A. mediterranei 的无细胞裂解物中孵育谷氨酰胺和 NAD 与 UDP

  DOI：

  10.1021/ja026628m

文献信息

• Characterization of the Early Stage Aminoshikimate Pathway in the Formation of 3-Amino-5-hydroxybenzoic Acid:  The RifN Protein Specifically Converts Kanosamine into Kanosamine 6-Phosphate
  作者：Kenji Arakawa、Rolf Müller、Taifo Mahmud、Tin-Wein Yu、Heinz G. Floss

  DOI：10.1021/ja0206339

  日期：2002.9.1

  The biosynthesis of 3-amino-5-hydroxybenzoic acid (AHBA), precursor of the ansamycin and mitomycin antibiotics, proceeds by the aminoshikimate pathway from 3,4-dideoxy-4-amino-D-arabino-heptulosonic acid 7-phosphate (aminoDAHP). Identification of RifN, product of one of three genes from the rifamycin biosynthetic gene cluster known to be essential for aminoDAHP formation, as a specific kanosamine

  安沙霉素和丝裂霉素抗生素的前体 3-氨基-5-羟基苯甲酸 (AHBA) 的生物合成通过氨基莽草酸途径从 3,4-二脱氧-4-氨基-D-阿拉伯-庚酮糖酸 7-磷酸 (aminoDAHP ）。鉴定 RifN，利福霉素生物合成基因簇中已知对氨基 DAHP 形成必不可少的三个基因之一的产物，因为特定的卡诺胺（3-脱氧-3-氨基-D-葡萄糖）6-激酶建立卡诺胺及其 6-磷酸盐作为 AHBA 形成的特定中间体。这暗示了氨基 DAHP 形成的假设反应序列，因此是 AHBA 生物合成的早期步骤，从 UDP-D-葡萄糖开始并通过 C-3 处的氧化和转氨作用引入氮。
• Probe Compound for Detecting and Isolating Enzymes and Means and Methods Using the Same
  申请人：Golyshin Peter N.

  公开号：US20120231972A1

  公开（公告）日：2012-09-13

  The present invention relates to a probe compound that can comprise any substrate or metabolite of an enzymatic reaction in addition to an indicator component, such as, for example, a fluorescence dye, or the like. Moreover, the present invention relates to means for detecting enzymes in form of an array, which comprises any number of probe compounds of the invention which each comprise a different metabolite of interconnected metabolites representing the central pathways in all forms of life. Moreover, the present invention relates to a method for detecting enzymes involving the application of cell extracts or the like to the array of the invention which leads to reproducible enzymatic reactions with the substrates. These specific enzymatic reactions trigger the indicator (e.g. a fluorescence signal) and bind the enzymes to the respective cognate substrates. Moreover, the invention relates to means for isolating enzymes in form of nanoparticles coated with the probe compound of the invention. The immobilisation of the cognate substrates or metabolites on the surface of nanoparticles by means of the probe compounds allows capturing and isolating the respective enzyme, e.g. for subsequent sequencing.
• [EN] PROBE COMPOUND FOR DETECTING AND ISOLATING ENZYMES AND MEANS AND METHODS USING THE SAME<br/>[FR] COMPOSÉ SONDE POUR DÉTECTER ET ISOLER DES ENZYMES ET MOYENS ET PROCÉDÉS POUR L'UTILISER
  申请人：HELMHOLTZ INFEKTIONSFORSCHUNG

  公开号：WO2010105851A1

  公开（公告）日：2010-09-23

  The present invention relates to a probe compound that can comprise any substrate or metabolite of an enzymatic reaction in addition to an indicator component, such as, for example, a fluorescence dye, or the like. Moreover, the present invention relates to means for detecting enzymes in form of an array, which comprises any number of probe compounds of the invention which each comprise a different metabolite of interconnected metabolites representing the central pathways in all forms of life. Moreover, the present invention relates to a method for detecting enzymes involving the application of cell extracts or the like to the array of the invention which leads to reproducible enzymatic reactions with the substrates. These specific enzymatic reactions trigger the indicator (e.g. a fluorescence signal) and bind the enzymes to the respective cognate substrates. Moreover, the invention relates to means for isolating enzymes in form of nanoparticles coated with the probe compound of the invention. The immobilisation of the cognate substrates or metabolites on the surface of nanoparticles by means of the probe compounds allows capturing and isolating the respective enzyme, e.g. for subsequent sequencing.
• Kanosamine Biosynthesis:  A Likely Source of the Aminoshikimate Pathway's Nitrogen Atom
  作者：Jiantao Guo、J. W. Frost

  DOI：10.1021/ja026628m

  日期：2002.9.1

  cell-free lysate of glutamine and NAD with UDP-glucose resulted in the formation of kanosamine. The bioconversion of UDP-glucose into kanosamine along with the bioconversion of kanosamine 6-phosphate into 4-amino-3,4-dideoxy-D-arabino-heptulosonic acid 7-phosphate and 3-amino-5-hydroxybenzoic acid suggests that kanosamine biosynthesis is the source of the aminoshikimate pathway's nitrogen atom.

  掺入氨基莽草酸酯途径的氮原子的生物合成来源一直是一个问题。3-氨基-3-脱氧-D-果糖 6-磷酸先前已被证明是 4-氨基-3,4-二脱氧-D-阿拉伯-庚糖酸 7-磷酸和 3-氨基-5-羟基苯甲酸的前体通过推断的 1-deoxy-1-imino-D-erythrose 4-phosphate 中间体在 Amycolatopsis mediterranei 无细胞提取物中产生酸。这项调查研究了天然产物卡诺胺可能是 3-amino-3-deoxy-D-fructose 6-phosphate 的前体的可能性。卡诺胺 6-磷酸是通过化学酶促途径合成的，并与 D-核糖 5-磷酸和磷酸烯醇丙酮酸一起在无细胞裂解物中孵育。4-氨基-3的形成，观察到4-双脱氧-D-阿拉伯-庚酮糖酸7-磷酸和3-氨基-5-羟基苯甲酸。随后在 A. mediterranei 的无细胞裂解物中孵育谷氨酰胺和 NAD 与 UDP
• Importance of Specific Hydrogen-Bond Donor−Acceptor Interactions for the Key Carbocycle-Forming Reaction Catalyzed by 2-Deoxy-<i>scyllo</i>-inosose Synthase in the Biosynthesis of 2-Deoxystreptamine-Containing Aminocyclitol Antibiotics
  作者：Tadashi Eguchi、Satoko Sasaki、Zhen Huang、Katsumi Kakinuma

  DOI：10.1021/jo011107n

  日期：2002.6.1

  the corresponding deoxyfluoro- and aminodeoxy-scyllo-inososes, respectively. In contrast, 3-F-G-6-P and 2-NH(2)-G-6-P were inactive in the cyclization reaction. Clearly, DOIS recognizes the G-6-P substrate through specific hydrogen-bonding interactions, i.e., through a hydrogen-donating group for C-2 and an accepting group for C-3 of the substrate. Modeling of DOIS based on the structure of evolutionary-related

  在临床上重要的氨基环醇抗生素的2-deoxystreptamine糖苷生物合成中的关键酶是2-deoxy-scyllo-inosose合酶（DOIS），它将普遍存在的D-葡萄糖6-磷酸酯（G-6-P）转化为特定的碳环2-脱氧鞘氨醇。在底物的所有氧化碳中，C-1，-4，-5和-6直接参与化学转化。为了深入了解C-2和C-3羟基，2-脱氧-2-氟，3-脱氧-3-氟，2-氨基-2-脱氧和3-氨基-3的作用-脱氧D-葡萄糖6-磷酸酯（2-FG-6-P，3-FG-6-P，2-NH（2）-G-6-P和3-NH（2）-G-6 -P）分别作为探针进行DOIS反应，因为氟取代基通常充当氢键受体，而生理上衍生自氨基的铵官能团作为氢键供体。在测试的那些当中，2-FG-6-P和3-NH（2）-G-6-P被DOIS用作底物，并分别转化为相应的脱氧氟-和氨基脱氧-鞘氨醇。相反，3-FG-6-P和2-NH（2）-G-6