(4S)-4-hydroxy-2,3,4,5-tetrahydro-(2S)-dipicolinic acid | 185103-33-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (4S)-4-hydroxy-2,3,4,5-tetrahydro-(2S)-dipicolinic acid
• 英文别名: (2S,4S)-4-hydroxy-2,3,4,5-tetrahydrodipicolinic acid；(2S,4S)-4-hydroxy-2,3,4,5-tetrahydropyridine-2,6-dicarboxylic acid
• CAS: 185103-33-7
• 化学式: C₇H₉NO₅
• 分子量: 187.152
• InChiKey: DVTPRYHENFBCII-IMJSIDKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  107
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (4S)-4-hydroxy-2,3,4,5-tetrahydro-(2S)-dipicolinic acid 、 2-氨基苯甲醛 以 水 为溶剂， 反应 1.0h， 生成 (3S,4aR)-3,4,4a,5-tetrahydrobenzo[b][1,6]naphthyridine-1,3-dicarboxylic acid
  参考文献：
  名称：

  LC–MS and NMR characterization of the purple chromophore formed in the o-aminobenzaldehyde assay of dihydrodipicolinate synthase

  摘要：

  The enzyme dihydrodipicolinate synthase (DHDPS) has been widely investigated as a target for new antibiotics. The o-aminobenzaldehyde (o-ABA) assay is routinely used as a highly specific, if qualitative, tool for DHDPS purification, whereby fractions containing active DHDPS appear purple upon addition of o-ABA. The purple adduct absorbs in the visible region (540 nm) but has never been characterized in the 50 years since it was first reported. Structural characterization of this purple compound has been performed by UV spectrophotometry, NMR spectroscopy and tandem mass spectrometry. The extinction coefficient of this chromophore was also determined. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.12.029
• 作为产物：
  描述：

  L-aspartate β-semialdehyde 、 piruvate 在 recombinant wild-type Escherichia coli dihydrodipicolinate synthase 作用下， 生成 (4S)-4-hydroxy-2,3,4,5-tetrahydro-(2S)-dipicolinic acid
  参考文献：
  名称：

  Exploring the dihydrodipicolinate synthase tetramer: How resilient is the dimer–dimer interface?

  摘要：

  Dihydrodipicolinate synthase (DHDPS, E.C. 4.2.1.52) is a tetrameric enzyme that catalyses the first committed step of the lysine biosynthetic pathway. Dimeric variants of DHDPS have impaired catalytic activity due to aberrant protein motions within the dimer unit. Thus, it is thought that the tetrameric structure functions to restrict these motions and optimise enzyme dynamics for catalysis. Despite the importance of dimer-dimer association, the interface between subunits of each dimer is small, accounting for only 4.3% of the total monomer surface area, and the structure of the interface is not conserved across species. We have probed the tolerance of dimer-dimer association to Mutation by introducing amino acid substitutions within the interface. All point mutations resulted in destabilisation of the 'dimer of dimers' tetramer Structure. Both the position of the Mutation in the interface and the physico-chemical nature of the substitution appeared to effect tetramerisation. Despite only weak destabilisation of the tetramer by some Mutations, catalytic activity was reduced to similar to 10-15% of the wild-type in all cases, suggesting that the dimer-dimer interface is finely tuned to optimise function. (C) 2009 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.abb.2009.11.014

文献信息

• HEPAROSAN-PRODUCING BACTERIUM AND HEPAROSAN MANUFACTURING METHOD
  申请人：Ajinomoto Co., Inc.

  公开号：EP3054005A1

  公开（公告）日：2016-08-10

  A method for producing heparosan is provided. Heparosan is produced by culturing an Escherichia bacterium having a heparosan-producing ability and modified so that expression of one or more kinds of genes selected from the group consisting of rbsR, rbsK, rbsB, hsrA, glgB, glgX, micF, rcsD, rcsB, ybiX, ybiI, ybiJ, ybiC, ybiB, rfaH, nusG, pcoR, pcoS, pcoE, yhcN, yhcO, aaeB, aaeA, aaeX, g1455, alpA, g1453, yrbA, mlaB, mlaC, mlaD, mlaE, mlaF, yrbG, norW, ybjI, ybjJ, ybjK, rybB, yjjY, yjtD, thrL, thrA, thrB, fruA, psuK, ytfT, yjfF, fbp, yagU, paoA, paoB, gsiC, gsiD, yliE, irp2, irp1, bhsA, ycfS, lepB, rnc, era, dapA, gcvR, bcp, hyfA, rpoE, nadB, yfiC, srmB, g1414, g1413, nuoE, nuoF, nuoG, glmZ, hemY, hemX, hemD, rlmL, artQ, artM, artJ, rlmC, YbjO, yejO, yejM, yejL, rpoS, ygbN, ygbM, ygbL, g3798, g3797, g3796, g3795, g3794, g3793, g3792, ryjA, soxR, soxS, yjcC, yjcB, efeU, and efeO genes is increased in a medium, and collecting heparosan from the medium.

  本发明提供了一种生产肝聚糖的方法。生产肝聚糖的方法是培养具有肝聚糖生产能力的埃希氏菌，并对其进行改造，以表达选自 rbsR、rbsK、rbsB、hsrA、glgB、glgX, micF, rcsD, rcsB, ybiX, ybiI, ybiJ, ybiC, ybiB, rfaH, nusG, pcoR, pcoS, pcoE, yhcN, yhcO, aaeB, aaeA, aaeX、g1455, alpA, g1453, yrbA, mlaB, mlaC, mlaD, mlaE, mlaF, yrbG, norW, ybjI, ybjJ, ybjK, rybB, yjjY, yjtD, thrL, thrA、thrB, fruA, psuK, ytfT, yjfF, fbp, yagU, paoA, paoB, gsiC, gsiD, yliE, irp2, irp1, bhsA, ycfS, lepB, rnc, era, dapA、gcvR, bcp, hyfA, rpoE, nadB, yfiC, srmB, g1414, g1413, nuoE, nuoF, nuoG, glmZ, hemY, hemX, hemD, rlmL, artQ, artM、g3798, g3797, g3796, g3795, g3794, g3793, g3792, ryjA, soxR, soxS, yjcC, yjcB, efeU, 和 efeO 基因在培养基中增加，并从培养基中收集肝聚糖。
• Heparosan-producing bacterium and heparosan manufacturing method
  申请人：AJINOMOTO CO., INC.

  公开号：US10611804B2

  公开（公告）日：2020-04-07

  A method for producing heparosan is provided. Heparosan is produced by culturing an Escherichia bacterium having a heparosan-producing ability and modified so that expression of one or more genes, such as rbsR, rbsK, rbsB, hsrA, glgB, glgX, micF, rcsD, rcsB, ybiX, ybil, ybiJ, ybiC, ybiB, rfaH, nusG, pcoR, pcoS, pcoE, yhcN, yhcO, aaeB, aaeA, aaeX, g1455, alpA, g1453, yrbA, mlaB, mlaC, mlaD, mlaE, mlaF, yrbG, norW, ybjI, ybjJ, ybjK, rybB, yjjY, yjtD, thrL, thrA, thrB, fruA, psuK, ytfT, yjfF, fbp, yagU, paoA, paoB, gsiC, gsiD, yliE, irp2, irp1, bhsA, ycfS, lepB, rnc, era, dapA, gcvR, bcp, hyfA, rpoE, nadB, yfiC, srmB, g1414, g1413, nuoE, nuoF, nuoG, glmZ, hemY, hemX, hemD, rlmL, artQ, artM, artJ, rlmC, ybjO, yejO, yejM, yejL, rpoS, ygbN, ygbM, ygbL, g3798, g3797, g3796, g3795, g3794, g3793, g3792, ryjA, soxR, soxS, yjcC, yjcB, efeU, and efeO, is/are increased in a medium, and collecting heparosan from the medium.

  提供了一种生产肝聚糖的方法。生产肝聚糖的方法是培养具有肝聚糖生产能力的埃希氏菌，并对其进行改造，使其表达一种或多种基因，如 rbsR、rbsK、rbsB、hsrA、glgB、glgX、micF、rcsD、rcsB、ybiX、ybil、ybiJ、ybiC、ybiB、rfaH、nusG、pcoR、pcoS、pcoE、yhc、ybil, ybiJ, ybiC, ybiB, rfaH, nusG, pcoR, pcoS, pcoE, yhcN, yhcO, aaeB, aaeA, aaeX, g1455, alpA, g1453, yrbA、mlaB, mlaC, mlaD, mlaE, mlaF, yrbG, norW, ybjI, ybjJ, ybjK, rybB, yjjY, yjtD, thrL, thrA, thrB, fruA, psuK、ytfT, yjfF, fbp, yagU, paoA, paoB, gsiC, gsiD, yliE, irp2, irp1, bhsA, ycfS, lepB, rnc, era, dapA, gcvR, bcp、hyfA, rpoE, nadB, yfiC, srmB, g1414, g1413, nuoE, nuoF, nuoG, glmZ, hemY, hemX, hemD, rlmL, artQ, artM, artJ、在培养基中增加 rlmC、ybjO、yejO、yejM、yejL、rpoS、ygbN、ygbM、ygbL、g3798、g3797、g3796、g3795、g3794、g3793、g3792、ryjA、soxR、soxS、yjcC、yjcB、efeU 和 efeO，并从培养基中收集肝聚糖。
• Heparosan-Producing Bacterium and Heparosan Manufacturing Method
  申请人：AJINOMOTO CO., INC.

  公开号：US20160201103A1

  公开（公告）日：2016-07-14

  A method for producing heparosan is provided. Heparosan is produced by culturing an Escherichia bacterium having a heparosan-producing ability and modified so that expression of one or more genes, such as rbsR, rbsK, rbsB, hsrA, glgB, glgX, micF, rcsD, rcsB, ybiX, ybiI, ybiJ, ybiC, ybiB, rfaH, nusG, pcoR, pcoS, pcoE, yhcN, yhcO, aaeB, aaeA, aaeX, g1455, alpA, g1453, yrbA, mlaB, mlaC, mlaD, mlaE, mlaF, yrbG, norW, ybjI, ybjJ, ybjK, rybB, yjjY, yjtD, thrL, thrA, thrB, fruA, psuK, ytfT, yjfF, fbp, yagU, paoA, paoB, gsiC, gsiD, yliE, irp2, irp1, bhsA, ycfS, lepB, rnc, era, dapA, gcvR, bcp, hyfA, rpoE, nadB, yfiC, srmB, g1414, g1413, nuoE, nuoF, nuoG, glmZ, hemY, hemX, hemD, rlmL, artQ, artM, artJ, rlmC, ybjO, yejO, yejM, yejL, rpoS, ygbN, ygbM, ygbL, g3798, g3797, g3796, g3795, g3794, g3793, g3792, ryjA, soxR, soxS, yjcC, yjcB, efeU, and efeO, is/are increased in a medium, and collecting heparosan from the medium.
• US9975928B2
  申请人：——

  公开号：US9975928B2

  公开（公告）日：2018-05-22
• Exploring the dihydrodipicolinate synthase tetramer: How resilient is the dimer–dimer interface?
  作者：Michael D.W. Griffin、Renwick C.J. Dobson、Juliet A. Gerrard、Matthew A. Perugini

  DOI：10.1016/j.abb.2009.11.014

  日期：2010.2

  Dihydrodipicolinate synthase (DHDPS, E.C. 4.2.1.52) is a tetrameric enzyme that catalyses the first committed step of the lysine biosynthetic pathway. Dimeric variants of DHDPS have impaired catalytic activity due to aberrant protein motions within the dimer unit. Thus, it is thought that the tetrameric structure functions to restrict these motions and optimise enzyme dynamics for catalysis. Despite the importance of dimer-dimer association, the interface between subunits of each dimer is small, accounting for only 4.3% of the total monomer surface area, and the structure of the interface is not conserved across species. We have probed the tolerance of dimer-dimer association to Mutation by introducing amino acid substitutions within the interface. All point mutations resulted in destabilisation of the 'dimer of dimers' tetramer Structure. Both the position of the Mutation in the interface and the physico-chemical nature of the substitution appeared to effect tetramerisation. Despite only weak destabilisation of the tetramer by some Mutations, catalytic activity was reduced to similar to 10-15% of the wild-type in all cases, suggesting that the dimer-dimer interface is finely tuned to optimise function. (C) 2009 Elsevier Inc. All rights reserved.