glycerin-pyruvic acid | 158647-63-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: glycerin-pyruvic acid
• 英文别名: 3-Deoxyhex-2-ulosonic acid；4,5,6-trihydroxy-2-oxohexanoic acid
• CAS: 158647-63-3
• 化学式: C₆H₁₀O₆
• 分子量: 178.142
• InChiKey: WPAMZTWLKIDIOP-UHFFFAOYSA-N

物化性质

• 沸点：
  467.5±45.0 °C(Predicted)
• 密度：
  1.582±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.3
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  115
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  甲醇 、 glycerin-pyruvic acid 在 三氟甲磺酸 作用下， 120.0 ℃ 、2.0 MPa 条件下， 反应 3.0h， 以95%的产率得到5-(羟基甲基)-2-糠酸甲酯
  参考文献：
  名称：

  一种制备2,5-呋喃二甲酸及其衍生物的方法

  摘要：

  本发明公开一种制备2,5‑呋喃二甲酸及其衍生物的方法，其特征在于，包括如下步骤：六碳糖酶水解产物与酸催化剂在溶剂中进行环合反应得到2,5‑呋喃二甲酸及其衍生物；其中，六碳糖为果糖、葡萄糖、麦芽糖、蔗糖、微晶纤维素中的至少一种。本发明选择性高、副产物少，收率高，产物纯度好，环境污染小，工艺操作简单，适合工业化生产。

  公开号：

  CN107417651A
• 作为产物：
  描述：

  sodium pyruvate 、 DL-甘油醛 在 pyruvate aldolase HpaI 、 cobalt(II) chloride 作用下， 反应 0.17h， 生成 glycerin-pyruvic acid
  参考文献：
  名称：

  Comparison of Two Metal-Dependent Pyruvate Aldolases Related by Convergent Evolution: Substrate Specificity, Kinetic Mechanism, and Substrate Channeling

  摘要：

  HpaI and BphI are two pyruvate class II aldolases found in aromatic meta-cleavage degradation pathways that catalyze similar reactions but are not related in sequence. Steady-state kinetic analysis of the aldol addition reactions and product inhibition assays showed that HpaI exhibits a rapid equilibrium random order mechanism while BphI exhibits a compulsory order mechanism, with pyruvate binding first. Both aldolases are able to utilize aldehyde acceptors two to five carbons in length; however, HpaI showed broader specificity and had a preference for aldehydes containing longer linear alkyl chains or C2-OH substitutions. Both enzymes were able to bind 2-keto acids larger than pyruvate, but only HpaI was able to utilize both pyruvate and 2-ketobutanoate as carbonyl donors in the aldol addition reaction. HpaI lacks stereospecific control producing racemic mixtures of 4-hydroxy-2-oxopentanoate (HOPA) from pyruvate and acetaldehyde while BphI synthesizes only (4S)-HOPA. BphI is also able to utilize acetaldehyde produced by the reduction of acetyl-CoA catalyzed by the associated aldehyde dehydrogenase, BphJ. This aldehyde was directly channeled from the dehydrogenase to the aldolase active sites, with an efficiency of 84%. Furthermore, the BphJ reductive deacylation reaction increased 4-fold when BphI was catalyzing the aldol addition reaction. Therefore, the BphI-BphJ enzyme complex exhibits unique bidirectionality in substrate channeling and allosteric activation.

  DOI：

  10.1021/bi100251u

文献信息

• [EN] DEHYDRATION AND CYCLIZATION OF ALPHA-, BETA-DIHYDROXY CARBONYL COMPOUNDS TO 2-SUBSTITUTED FURAN DERIVATIVES<br/>[FR] DÉSHYDRATATION ET CYCLISATION DE COMPOSÉS ALPHA-, BÊTA-DIHYDROXYCARBONYLE EN DÉRIVÉS DE FURANE SUBSTITUÉS EN POSITION 2
  申请人：ARCHER DANIELS MIDLAND CO

  公开号：WO2019199570A1

  公开（公告）日：2019-10-17

  Processes are disclosed for the synthesis of 2-substituted furan derivatives from a substrate having a carbonyl functional group (C=O), with hydroxy-substituted carbon atoms at alpha and beta positions, relative to the carbonyl functional group. In one embodiment, an alpha-, beta-dihydroxy carboxylate is dehydrated to form a dicarbonyl intermediate by transformation of the alpha-hydroxy group to a second carbonyl group and removal of the beta-hydroxy group. The dicarbonyl intermediate undergoes cyclization and dehydration to produce the 2-substituted furan derivative. Optionally, a further step of oxidation may be carried out, for example to convert a hydroxymethyl group, as a 5-substituted furan ring, to a carboxy group of 2,5-furan dicarboxylic acid.

  本文揭示了一种从具有羰基官能团（C = O）的底物合成2-取代呋喃衍生物的过程，其中α和β位置相对于羰基官能团具有羟基取代的碳原子。在一种实施方式中，α，β-二羟基羧酸酯通过将α-羟基团转化为第二个羰基团并去除β-羟基团而脱水形成二羰基中间体。该二羰基中间体经历环化和脱水反应以产生2-取代呋喃衍生物。可选地，可以进行进一步的氧化步骤，例如将5-取代呋喃环的羟甲基团转化为2,5-呋喃二羧酸的羧基团。
• [EN] DEHYDRATION AND CRACKING OF ALPHA-, BETA-DIHYDROXY CARBONYL COMPOUNDS TO LACTIC ACID AND OTHER PRODUCTS<br/>[FR] DÉSHYDRATATION ET CRAQUAGE DE COMPOSÉS ALPHA-, BÊTA-DIHYDROXYCARBONYLE EN ACIDE LACTIQUE ET AUTRES PRODUITS
  申请人：ARCHER DANIELS MIDLAND CO

  公开号：WO2019199540A1

  公开（公告）日：2019-10-17

  Processes are disclosed for the synthesis of a cracked product from a starting substrate having a carbonyl functional group (C=O), with hydroxy-substituted carbon atoms at alpha and beta positions, relative to the carbonyl functional group. In one embodiment, an alpha-, beta-dihydroxy carboxylic acid or carboxylate is dehydrated to form a dicarbonyl intermediate by transformation of the alpha-hydroxy group to a second carbonyl group and removal of the beta-hydroxy group. The dicarbonyl intermediate is cracked to form the cracked product in which the first and second carbonyl groups are preserved. Either or both of (i) the cracked product and (ii) a second cracked product generated from cleavage of a carbon-carbon bond of the dicarbonyl intermediate, may be hydrogenated to form additional products.

  本发明公开了从具有羰基官能团（C = O）的起始底物合成裂解产物的方法，其中在α和β位置相对于羰基官能团具有羟基取代的碳原子。在一种实施例中，α，β-二羟基羧酸或羧酸盐通过将α-羟基转化为第二个羰基团并去除β-羟基而脱水形成二羰基中间体。该二羰基中间体裂解形成裂解产物，其中保留第一和第二羰基团。裂解产物和/或从二羰基中间体的碳-碳键裂解产生的第二裂解产物可以氢化以形成额外的产物。
• [EN] DEHYDRATION AND AMINATION OF ALPHA-, BETA-DIHYDROXY CARBONYL COMPOUNDS TO ALPHA-AMINO ACIDS<br/>[FR] DÉSHYDRATATION ET AMINATION DE COMPOSÉS ALPHA-, BÊTA-DIHYDROXYCARBONYLE EN ACIDES ALPHA-AMINÉS
  申请人：ARCHER DANIELS MIDLAND CO

  公开号：WO2019199518A1

  公开（公告）日：2019-10-17

  Processes are disclosed for synthesizing an α-amino acid or α-amino acid derivative, from a starting compound having a carbonyl functional group (C=O), with hydroxy-substituted carbon atoms at alpha (α) and beta (β) positions, relative to the carbonyl functional group. An α-, β-dihydroxy carboxylic acid or carboxylate is dehydrated to form a dicarbonyl intermediate by transformation of the α-hydroxy group to a second carbonyl group (adjacent a carbonyl group of the starting compound) and removal of the β-hydroxy group. This dicarbonyl intermediate is optionally cracked to form a second dicarbonyl intermediate having fewer carbon atoms but preserving the first and second carbonyl groups. Either or both of the dicarbonyl intermediate and the cracked dicarbonyl intermediate are then reductively aminated.

  揭示了一种从具有羰基官能团（C = O）的起始化合物合成α-氨基酸或α-氨基酸衍生物的过程，该起始化合物在α（α）和β（β）位置具有羟基取代碳原子，相对于羰基官能团。 α，β-二羟基羧酸或羧酸盐通过将α-羟基转化为第二个羰基基团（与起始化合物的羰基基团相邻）并去除β-羟基而脱水形成二羰基中间体。该二羰基中间体可以选择性地裂解以形成第二个二羰基中间体，其具有更少的碳原子，但保留第一和第二个羰基基团。然后，可以对二羰基中间体和裂解的二羰基中间体中的任一或任两个进行还原胺化。
• Probe compound for detecting and isolating enzymes and means and methods using the same
  申请人：Helmholtz-Zentrum für Infektionsforschung GmbH

  公开号：EP2230312A1

  公开（公告）日：2010-09-22

  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.

  本发明涉及一种探针化合物，它可以包括酶反应的任何底物或代谢物，此外还包括指示成分，例如荧光染料或类似物。此外，本发明还涉及以阵列形式检测酶的方法，该阵列由任意数量的本发明探针化合物组成，每种探针化合物由代表所有生命形式中中心途径的相互关联的代谢物中的不同代谢物组成。此外，本发明还涉及一种检测酶的方法，该方法涉及将细胞提取物或类似物应用于本发明的阵列，从而导致与底物发生可重复的酶反应。这些特定的酶反应会触发指示剂（如荧光信号），并将酶与各自的同源底物结合。此外，本发明还涉及以涂覆有本发明探针化合物的纳米颗粒形式分离酶的方法。通过探针化合物将同源底物或代谢物固定在纳米颗粒表面，可以捕获和分离相应的酶，例如用于后续测序。
• PROCESS FOR ENZYMATIC OXIDATION OF LINEAR CARBOHYDRATES
  申请人：Technische Universität München

  公开号：EP3460067A1

  公开（公告）日：2019-03-27

  A process for enzymatic oxidation of a terminal group of a linear carbohydrate is disclosed, wherein a carbohydrate of formula (I): TU-X-Y-TOG, wherein TU is a terminal unit selected from -CH2OH, -CHO, -COOH, and -C1-C4 alkyl; X is a linear carbohydrate chain comprising 0 to 18 units [CR1R2], wherein in each unit R1 and R2 independently can be hydrogen, hydroxyl, C1-C4 alkyl, or can together form a keto group, Y is -CHOH, -CHNH2 or -CHSH and TOG is an oxidzable terminal unit selected from -CH2OH and -CHO; is contacted with an NAD+ dependent short chain dehydrogenase/reductase for oxidation of TOG.

  本发明公开了一种线性碳水化合物末端基团的酶促氧化工艺，其中碳水化合物为式(I)：TU-X-Y-TOG，其中 TU 是选自-CH2OH、-CHO、-COOH 和-C1-C4 烷基的末端单元；X 是由 0 至 18 个单元组成的线性碳水化合物链[CR1R2]，其中每个单元中的 R1 和 R2 可独立地为氢、羟基、C1-C4 烷基或可共同形成酮基，Y 是-CHOH、-CHNH2 或-CHSH，TOG 是选自-CH2OH 和-CHO 的可氧化末端单元；与依赖于 NAD+ 的短链脱氢酶/还原酶接触以氧化 TOG。