cis-(homo)3-aconitic acid | 1186647-63-1

• 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: cis-(homo)3-aconitic acid
• 英文别名: cis-Trihomoaconitic acid；(Z)-hex-1-ene-1,2,6-tricarboxylic acid
• CAS: 1186647-63-1
• 化学式: C₉H₁₂O₆
• 分子量: 216.191
• InChiKey: NGULBISQWGMRGK-WAYWQWQTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  112
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  cis-(homo)3-aconitic acid 在 2-环己胺基乙磺酸 、 potassium chloride 、 potassium hydroxide 作用下， 生成 (2R,3S)-(homo)3-isocitric acid
  参考文献：
  名称：

  Substrate Specificity Determinants of the Methanogen Homoaconitase Enzyme: Structure and Function of the Small Subunit^,

  摘要：

  The aconitase family of hydro-lyase enzymes includes three classes of proteins that catalyze the isomerization of alpha-hydroxy acids to beta-hydroxy acids. Besides aconitase, isopropylmalate isomerase (IPMI) proteins specifically catalyze the isomerization of alpha,beta-dicarboxylates with hydrophobic gamma-chain groups, and homoaconitase (HACN) proteins catalyze the isomerization of tricarboxylates with variable chain length gamma-carboxylate groups. These enzymes' stereospecific hydro-lyase activities make them attractive catalysts to produce diastereomers from unsaturated precursors. However, sequence similarity and convergent evolution among these proteins lead to widespread misannotation and uncertainty about gene function. To Find the substrate specificity determinants of homologous IPMI and HACN proteins from Methanocaldococcus jannaschii, the small-subunit HACN protein (MJ1271) was crystallized for X-ray diffraction. The Structural model showed characteristic residues in a flexible loop region between alpha 2 and alpha 3 that distinguish HACN from IPMI and aconitase proteins. Site-directed mutagenesis of MJ1271 produced loop-region variant proteins that were reconstituted with wild-type MJ1003 large-subunit protein. The heteromers formed promiscuous hydro-lyases with reduced activity but broader substrate specificity. Both R26K and R26V variants formed relatively efficient IPMI enzymes, while the T27A variant had uniformly lower specificity constants for both IPMI and HACN substrates. The R26V T27Y variant resembles the MJ1277 IPMI small subunit in its flexible loop sequence but demonstrated the broad substrate specificity of the R26V variant. These mutations may reverse the evolution of HACN activity from an ancestral IPMI gene, demonstrating the evolutionary potential for promiscuity in hydro-lyase enzymes. Understanding these specificity determinants enables the functional reannotation of paralogous HACN and IPMI genes in numerous genome sequences. These structural and kinetic results will help to engineer new stereospecific hydro-lyase enzymes for chemoenzymatic syntheses.

  DOI：

  10.1021/bi901766z

文献信息

• PREPARATION OF ADIPIC ACID
  申请人：Raemakers-Franken Petronella Catharina

  公开号：US20120028320A1

  公开（公告）日：2012-02-02

  The invention relates to a method for preparing adipic acid, comprising converting alpha-ketoglutaric acid (AKG) into alpha-ketoadipic acid (AKA), converting alpha-ketoadipic acid into alpha-ketopimelic acid (AKP), converting alpha-ketopimelic acid into 5-formylpentanoic acid (5-FVA), and converting 5-formylpentanoic acid into adipic acid, wherein at least one of these conversions is carried out using a heterologous biocatalyst.The invention further relates to a heterologous cell, comprising one or more heterologous nucleic acid sequences encoding one or more heterologous enzymes capable of catalysing at least one reaction step in said method.

  本发明涉及一种制备己二酸的方法，包括将α-酮戊二酸转化为α-酮己二酸，将α-酮己二酸转化为α-酮庚二酸，将α-酮庚二酸转化为5-甲酰戊酸，将5-甲酰戊酸转化为己二酸，其中至少有一种转化是使用异源生物催化剂进行的。本发明还涉及一种异源细胞，包括一个或多个异源核酸序列，编码能够催化所述方法中至少一个反应步骤的一个或多个异源酶。
• BIOLOGICAL SYNTHESIS OF DIFUNCTIONAL ALKANES FROM CARBOHYDRATE FEEDSTOCKS
  申请人：Celexion, LLC

  公开号：US20140206069A1

  公开（公告）日：2014-07-24

  Aspects of the invention relate to methods for the production of difunctional alkanes in host cells. In particular, aspects of the invention describe components of genes associated with the difunctional alkane production from carbohydrate feedstocks in host cells. More specifically, aspects of the invention describe metabolic pathways for the production of adipic acid, aminocaproic acid, caprolactam, and hexamethylenediamine via 2-ketopimelic acid.

  本发明涉及在宿主细胞中生产二官能烷的方法。具体而言，本发明描述了与碳水化合物原料在宿主细胞中生产二官能烷相关的基因组成部分。更具体地，本发明描述了通过2-酮基脂肪酸代谢途径生产己二酸、氨基己酸、己内酰胺和六亚甲基二胺的代谢途径。
• BIOCONVERSION PROCESS FOR PRODUCING NYLON-7, NYLON-7,7 AND POLYESTERS
  申请人：INVISTA TECHNOLOGIES S.a.r.l.

  公开号：US20150337275A1

  公开（公告）日：2015-11-26

  Embodiments of the present invention relate to methods for the biosynthesis of di- or trifunctional C7 alkanes in the presence of isolated enzymes or in the presence of a recombinant host cell expressing those enzymes. The di- or trifunctional C7 alkanes are useful as intermediates in the production of nylon-7, nylon-7,x, nylon-x,7, and polyesters.

  本发明实施例涉及在分离酶存在或在表达这些酶的重组宿主细胞存在下，生物合成双或三功能C7烷的方法。这些双或三功能C7烷在生产尼龙-7、尼龙-7，x、尼龙-x，7和聚酯中作为中间体是有用的。
• Bioconversion Process for Producing Nylon-7, Nylon-7, 7 and Polyesters
  申请人：Pearlman Paul S.

  公开号：US20140242655A1

  公开（公告）日：2014-08-28

  Embodiments of the present invention relate to methods for the biosynthesis of di- or trifunctional C7 alkanes in the presence of isolated enzymes or in the presence of a recombinant host cell expressing those enzymes. The di- or trifunctional C7 alkanes are useful as intermediates in the production of nylon-7, nylon-7,x, nylon-x,7, and polyesters.
• US8778642B2
  申请人：——

  公开号：US8778642B2

  公开（公告）日：2014-07-15