D-lyxo-hexos-2-ulose

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: D-lyxo-hexos-2-ulose
• 英文别名: 2-keto-D-galactose；2-dehydro-D-galactopyranose；(4S,5R,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-one
• 化学式: C₆H₁₀O₆
• 分子量: 178.142
• InChiKey: FYWIDDXZIOQEQU-XDJBDKDSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.2
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  107
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  D-lyxo-hexos-2-ulose 在 (S)-(-)- α-甲基苄胺 、 ω-transaminase from Chromobacterium violaceum 作用下， 生成 (4R,5R,6R)-3-amino-6-(hydroxymethyl)oxane-2,4,5-triol
  参考文献：
  名称：

  通过氧化还原酶和转氨酶级联生物催化生产氨基碳水化合物

  摘要：

  植物来源的碳水化合物是一种丰富的可再生资源。将碳水化合物转化为新产品，包括用于生物材料应用的胺官能化构建块，可以降低对化石资源的依赖。在此，展示了氨基碳水化合物（包括寡糖）的生物催化生产路线。在每种情况下，均使用来自禾谷镰刀菌的半乳糖氧化酶或来自双孢蘑菇的吡喃糖脱氢酶，然后使用来自紫色色杆菌的 ω-转氨酶( Cvi -ω-TA)进行两步生物催化，以功能化含d-半乳糖的碳水化合物。通过质谱法证实了6-氨基-6-脱氧-d-半乳糖、2-氨基-2-脱氧-d-半乳糖和2-氨基-2-脱氧-6-醛-d-半乳糖的形成。Cvi -ω-TA 对 6-醛-d-半乳糖的活性最高，其中 6-氨基-6-脱氧-d-半乳糖的最高产率 (67%) 在允许同时氧化d-半乳糖的反应中实现。半乳糖和由此产生的 6-醛-d-半乳糖的转氨作用。

  DOI：

  10.1002/cssc.201802580
• 作为产物：
  描述：

  D-吡喃葡萄糖 在 pyranose dehydrogenase from Agaricusbisporus 、 对苯醌 作用下， 生成 D-lyxo-hexos-2-ulose
  参考文献：
  名称：

  通过氧化还原酶和转氨酶级联生物催化生产氨基碳水化合物

  摘要：

  植物来源的碳水化合物是一种丰富的可再生资源。将碳水化合物转化为新产品，包括用于生物材料应用的胺官能化构建块，可以降低对化石资源的依赖。在此，展示了氨基碳水化合物（包括寡糖）的生物催化生产路线。在每种情况下，均使用来自禾谷镰刀菌的半乳糖氧化酶或来自双孢蘑菇的吡喃糖脱氢酶，然后使用来自紫色色杆菌的 ω-转氨酶( Cvi -ω-TA)进行两步生物催化，以功能化含d-半乳糖的碳水化合物。通过质谱法证实了6-氨基-6-脱氧-d-半乳糖、2-氨基-2-脱氧-d-半乳糖和2-氨基-2-脱氧-6-醛-d-半乳糖的形成。Cvi -ω-TA 对 6-醛-d-半乳糖的活性最高，其中 6-氨基-6-脱氧-d-半乳糖的最高产率 (67%) 在允许同时氧化d-半乳糖的反应中实现。半乳糖和由此产生的 6-醛-d-半乳糖的转氨作用。

  DOI：

  10.1002/cssc.201802580

文献信息

• Purification, Characterization, and Molecular Cloning of a Pyranose Oxidase from the Fruit Body of the Basidiomycete,<i>Tricholoma matsutake</i>
  作者：Yoshimitsu TAKAKURA、Shigeru KUWATA

  DOI：10.1271/bbb.67.2598

  日期：2003.1

  A new H2O2-generating pyranose oxidase was purified as a strong antifungal protein from an arbuscular mycorrhizal fungus, Tricholoma matsutake. The protein showed a molecular mass of 250 kDa in gel filtration, and probably consisted of four identical 62 kDa subunits. The protein contained flavin moiety and it oxidized D-glucose at position C-2. H2O2 and D-glucosone produced by the pyranose oxidase reaction showed antifungal activity, suggesting these compounds were the molecular basis of the antifungal property. The Vmax, Km, and kcat for D-glucose were calculated to be 26.6 U/mg protein, 1.28 mM, and 111/s, respectively. The enzyme was optimally active at pH 7.5 to 8.0 and at 50°C. The preferred substrate was D-glucose, but 1,5-anhydro-D-glucitol, L-sorbose, and D-xylose were also oxidized at a moderate level. The cDNA encodes a protein consisting of 564 amino acids, showing 35.1% identity to Coriolus versicolor pyranose oxidase. The recombinant protein was used for raising the antibody.

  从一种内生菌根真菌松口蘑中纯化得到一种新的H2O2生成吡喃糖氧化酶，该酶具有强烈的抗真菌蛋白活性。该蛋白在凝胶过滤中表现出250 kDa的分子质量，可能由四个相同的62 kDa亚基组成。该蛋白含有黄素部分，并在C-2位置氧化D-葡萄糖。由吡喃糖氧化酶反应产生的 和D-葡糖酮具有抗真菌活性，表明这些化合物是其抗真菌特性的分子基础。D-葡萄糖的Vmax、Km和kcat分别为26.6 U/mg蛋白、1.28 mM和111/s。该酶在pH 7.5至8.0和50°C下活性最佳。其首选底物是D-葡萄糖，但1,5-脱水-D-山梨醇、L-山梨糖和D-木糖也能在中等程度上被氧化。该cDNA编码一个由564个氨基酸组成的蛋白质，与杂色革盖菌的吡喃糖氧化酶有35.1%的同源性。使用重组蛋白制备抗体。
• One‐Pot Bioconversion of <scp>l</scp> ‐Arabinose to <scp>l</scp> ‐Ribulose in an Enzymatic Cascade
  作者：Litavadee Chuaboon、Thanyaporn Wongnate、Pangrum Punthong、Cholpisit Kiattisewee、Narin Lawan、Chia‐Yi Hsu、Chun‐Hung Lin、Uwe T. Bornscheuer、Pimchai Chaiyen

  DOI：10.1002/anie.201814219

  日期：2019.2.18

  wild‐type P2O is specific for the oxidation of six‐carbon sugars, a pool of P2O variants was generated based on rational design to change the specificity of the enzyme towards the oxidation of l‐arabinose at the C2‐position. The variant T169G was identified as the best candidate, and this had an approximately 40‐fold higher rate constant for the flavin reduction (sugar oxidation) step, as compared to the wild‐type

  这项工作报告了一锅法式酶联反应级联反应，它利用吡喃糖2-氧化酶（P2O），木糖还原酶，甲酸脱氢酶和过氧化氢酶催化的四个反应将l-阿拉伯糖完全转化为l-核糖。由于野生型P2O对六碳糖的氧化具有特异性，因此在合理设计的基础上生成了一系列P2O变体，以改变酶对l氧化的特异性。C2位置的阿拉伯糖。T169G变体被认为是最佳候选者，与野生型酶相比，其黄素还原（糖氧化）步骤的速率常数高约40倍。使用量子力学/分子力学（QM / MM）分子动力学（MD）进行的计算表明，这种改进是由于l-阿拉伯糖在轴向C4-OH处的空间效应减少，从而缩短了两者之间的距离C2-H和黄素N5，促进氢化物转移并降低黄素含量。
• C-2 and C-3 oxidation of d-Glc, and C-2 oxidation of d-Gal by pyranose dehydrogenase from Agaricus bisporus
  作者：Jindřich Volc、Petr Sedmera、Petr Halada、Věra Přikrylova、Geoffrey Daniel

  DOI：10.1016/s0008-6215(98)00151-7

  日期：1998.8

  The quinone-dependent sugar oxidoreductase, pyranose dehydrogenase purified from the basidiomycete Agaricus bisporus catalyzed C-2 and C-3 oxidation of D-Glc to D-arabino-hexos-2-ulose (2-keto-D-Glc) and, preferentially, D-ribo-hexos-3-ulose (3-keto-D-Glc). The two aldoketoses accumulated only transiently in the reaction mixture being continually converted to the same end-product, D-erythro-hexos-2,3-diulose (2,3-diketo-D-Glc). D-Gal was oxidized by pyranose dehydrogenase and 1,4-benzoquinone exclusively at C-2 to produce D-lyxo-hexos-2-ulose (2-keto-D-Gal). Structures of the enzyme reaction products were deduced from their N,N-diphenylhydrazone derivatives. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Conversion of <scp>d</scp>‐Galactose to <scp>d</scp>‐<i>threo</i>‐Hexos‐2,3‐diulose by Fungal Pyranose Oxidase
  作者：Jind[rcheck]ich Volc、Petr Sedmera、Petr Halada、Padmanabh Dwivedi、Maria Costa‐Ferreira

  DOI：10.1081/car-120021701

  日期：2003.1.6

  Pyranose oxidase (pyranose:O-2 2-oxidoreductase, EC 1.1.3.10) purified from mycelia of the basidiomycete fungi Trametes versicolor and Oudemansiella mucida catalyzed oxidation Of D-galactose successively at C-2 and C-3 to D-threo-hexos-2,3-diulose (2,3-dehydro-D-galactose, 2,3-diketo-D-galactose) in the yields up to 80%. The sites of oxidation were deduced from structures of the N,N-diphenylhydrazone derivatives of the reaction products. Under the reaction conditions used, the diulose was susceptible to non-enzymatic oxidative decarboxylation to D-threo-pentos-2-ulose (2-dehydro-D-xylose, 2-keto-D-xylose) in yields of 5-10%.
• REMOVAL OF SENESCENCE-ASSOCIATED MACROPHAGES
  申请人：EVERON BIOSCIENCES, INC.

  公开号：US20200123127A1

  公开（公告）日：2020-04-23

  In various aspects and embodiments provided are compounds, compositions and methods relating to aging, senescent cells (SCs) and/or senescence associate macrophages (SAMs). In certain aspects and embodiments provided are compounds and compositions that selectively kill or reprogram senescent cells (SCs) and or senescence associate macrophages (SAMs) and associated methods. In some embodiments, the compounds compositions and methods treat or reverse aging organism Normal tissue and/or age-related diseases.