L-xylo-3-hexulose

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: L-xylo-3-hexulose
• 英文别名: (2R,4R,5S)-1,2,4,5,6-pentahydroxyhexan-3-one
• 化学式: C₆H₁₂O₆
• 分子量: 180.158
• InChiKey: DWJZKGYQNOQQEZ-VPENINKCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.3
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  118
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  L-xylo-3-hexulose 在 recombinant L-xylo-3-hexulose reductase LXR₄ 、 还原型辅酶II(NADPH)四钠盐 作用下， 生成 山梨醇
  参考文献：
  名称：

  l-xylo-3-Hexulose Reductase Is the Missing Link in the Oxidoreductive Pathway for d-Galactose Catabolism in Filamentous Fungi

  摘要：

  In addition to the well established Leloir pathway for the catabolism of D-galactose in fungi, the oxidoreductive pathway has been recently identified. In this oxidoreductive pathway, D-galactose is converted via a series of NADPH-dependent reductions and NAD(+)-dependent oxidations into D-fructose. The pathway intermediates include galactitol, L-xylo-3-hexulose, and D-sorbitol. This study identified the missing link in the pathway, the L-xylo-3-hexulose reductase that catalyzes the conversion of L-xylo-3-hexulose to D-sorbitol. In Trichoderma reesei (Hypocrea jecorina) and Aspergillus niger, we identified the genes lxr4 and xhrA, respectively, that encode the L-xylo-3-hexulose reductases. The deletion of these genes resulted in no growth on galactitol and in reduced growth on D-galactose. The LXR4 was heterologously expressed, and the purified protein showed high specificity for L-xylo-3-hexulose with a K-m = 2.0 +/- 0.5 mM and a V-max = 5.5 +/- 1.0 units/mg. We also confirmed that the product of the LXR4 reaction is D-sorbitol.

  DOI：

  10.1074/jbc.m112.372755
• 作为产物：
  描述：

  D-galactitol 在 recombinant L-xylo-3-hexulose reductase LXR₄ 、 nicotinamide adenine dinucleotide phosphate 作用下， 生成 L-xylo-3-hexulose
  参考文献：
  名称：

  l-xylo-3-Hexulose Reductase Is the Missing Link in the Oxidoreductive Pathway for d-Galactose Catabolism in Filamentous Fungi

  摘要：

  In addition to the well established Leloir pathway for the catabolism of D-galactose in fungi, the oxidoreductive pathway has been recently identified. In this oxidoreductive pathway, D-galactose is converted via a series of NADPH-dependent reductions and NAD(+)-dependent oxidations into D-fructose. The pathway intermediates include galactitol, L-xylo-3-hexulose, and D-sorbitol. This study identified the missing link in the pathway, the L-xylo-3-hexulose reductase that catalyzes the conversion of L-xylo-3-hexulose to D-sorbitol. In Trichoderma reesei (Hypocrea jecorina) and Aspergillus niger, we identified the genes lxr4 and xhrA, respectively, that encode the L-xylo-3-hexulose reductases. The deletion of these genes resulted in no growth on galactitol and in reduced growth on D-galactose. The LXR4 was heterologously expressed, and the purified protein showed high specificity for L-xylo-3-hexulose with a K-m = 2.0 +/- 0.5 mM and a V-max = 5.5 +/- 1.0 units/mg. We also confirmed that the product of the LXR4 reaction is D-sorbitol.

  DOI：

  10.1074/jbc.m112.372755

文献信息

• L-Xylo-3-hexulose, a new rare sugar produced by the action of acetic acid bacteria on galactitol, an exception to Bertrand Hudson's rule
  作者：Yirong Xu、Ping Chi、Jiyang Lv、Muhammad Bilal、Hairong Cheng

  DOI：10.1016/j.bbagen.2020.129740

  日期：2021.1

  dehydrogenases that oxidize polyhydric alcohols to rare sugars, which can be used as a healthy alternative for traditional sugars and sweeteners. These oxidation reactions obey the generally accepted Bertrand Hudson's rule, in which only the polyhydric alcohols that possess cis d-erythro hydroxyl groups can be oxidized to 2-ketoses using PQQ as a cofactor, while the polyhydric alcohols excluding cis d-erythro

  背景 在醋酸细菌中，如氧化葡糖杆菌或蜡状葡糖杆菌，周质中的吡咯并喹啉醌（PQQ）充当几种膜结合脱氢酶的氧化还原辅因子，这些酶将多元醇氧化为稀有糖，可以用作传统糖的健康替代品和甜味剂。这些氧化反应服从普遍接受贝特朗Hudson的规则，其中仅具有多元醇的顺式d -赤羟基可以被氧化成使用PQQ作为辅因子2-酮糖，而多元醇不含顺d排除-赤羟基消除了PQQ依赖的膜结合脱氢酶的氧化作用。 方法 制备G.oxydans的膜级分，并在有或没有PQQ作为辅因子的情况下用作氧化半乳糖醇的无细胞催化剂。 结果 在这项研究中，我们报道了一个有趣的氧化反应，该多元醇半乳糖醇（卫矛醇），其不具有顺d -赤羟基，可以通过PQQ依赖性膜结合脱氢酶（S）乙酸菌中的氧化C-3和C-5羟基可产生稀有的糖1 -xylo-3-hexulose和d - tagatose。 结论 这种反应可能是贝特朗·哈德森规则的一个例外。 一般意义
• [DE] VERFAHREN ZUR ENZYMATISCHEN GALACTOSYLIERUNG VON MONO- UND OLIGOSACCHARIDEN<br/>[EN] METHOD FOR THE ENZYMATIC GALACTOSYLATION OF MONOSACCHARIDES AND OLIGOSACCHARIDES<br/>[FR] PROCEDE DE GALACTOSYLATION ENZYMATIQUE DE MONOSACCHARIDES ET D'OLIGOSACCHARIDES
  申请人：HOECHST AKTIENGESELLSCHAFT

  公开号：WO1996035801A1

  公开（公告）日：1996-11-14

  (DE) Die Erfindung betrifft ein verbessertes Verfahren zur enzymatischen Galactosylierung von Mono- und Oligosacchariden unter in situ Regeneration des Nucleotidzuckers (bzw. des Nucleosiddiphosphatzuckers) in Gegenwart von Saccharose-Synthase, $g(b)-1-4-Galactosyltransferase und Uridindiphosphat-Glucose-4'-Epimerase (UDP-Glucose-4'-Epimerase), bei welchem die Uridindiphosphat-Glucose-4'-Epimerase mittels eines Ketonzuckerderivats reaktiviert wird.(EN) The invention concerns an improved method for the enzymatic galactosylation of monosaccharides and oligosaccharides with in situ regeneration of the nucleotide sugar (or the nucleoside diphosphate sugar) in the presence of saccharose synthase, $g(b)-1-4-galactosyl transferase and uridine diphosphate glucose-4'-epimerase (UDP glucose-4'-epimerase), the method calling for the uridine diphosphate glucose-4'-epimerase to be reactivated by a ketone sugar derivative.(FR) L'invention concerne un procédé perfectionné de galatosylation enzymatique de monosaccharides et d'oligosaccharides avec régénération in situ du sucre de nucléotide (par ex. du sucre de diphosphate de nucléoside) en présence de saccharose-synthase, de 1-4-galactosyltransférase et d'uridine diphosphate-glucose-4'-épimérase (UDP-glucose-4'-épimérase). Selon ce procédé, l'uridine diphosphate-glucose-4'-épimérase est réactivée à l'aide d'un dérivé de sucre cétonique.

  这项发明涉及一种改进的酶促葡萄糖化方法，用于对单糖和多糖进行葡萄糖化处理。该方法基于在核苷苷苷酶或其他核苷酸二磷酸糖酶存在下，通过内环境下再生核苷苷三磷酸糖或其他核苷酸二磷酸糖（如尿苷二磷酸葡萄糖）。该方法中，尿苷二磷酸葡萄糖-4’-转氨酶通过一种酮糖的衍生物进行活化。
• Trimethysilylation and G.L.C.-mass spectrometry of 3-ketoses and 2-heptuloses
  作者：Takuo Okuda、Setsuo Saito、Masayuki Hayashi

  DOI：10.1016/s0008-6215(00)84049-5

  日期：1979.1
• Morgenlie, Svein, Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1987, vol. 41, # 10, p. 745 - 748
  作者：Morgenlie, Svein

  DOI：——

  日期：——
• VERFAHREN ZUR ENZYMATISCHEN GALACTOSYLIERUNG VON MONO- UND OLIGOSACCHARIDEN
  申请人：Aventis Research & Technologies GmbH & Co. KG

  公开号：EP0827549B1

  公开（公告）日：2001-09-26