L-fuculose 1-phosphate | 92418-41-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: L-fuculose 1-phosphate
• 英文别名: [(3R,4R,5S)-3,4,5-trihydroxy-2-oxohexyl] dihydrogen phosphate
• CAS: 92418-41-2
• 化学式: C₆H₁₃O₈P
• 分子量: 244.138
• InChiKey: KNYGWWDTPGSEPD-LFRDXLMFSA-N

物化性质

• 沸点：
  595.1±60.0 °C(Predicted)
• 密度：
  1.697±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3.3
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  145
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  L-fuculose 1-phosphate 反应 21.0h， 生成 L-墨角藻糖
  参考文献：
  名称：

  Enzymic Synthesis of L-Fucose and Analogs

  摘要：

  DOI：

  10.1021/jo00127a052
• 作为产物：
  描述：

  L(-)岩藻糖 在 L-fucose isomerase from Escherichia coli 、 L-rhamnulose kinase from Thermotoga maritima MSB₈ 、 magnesium 、 锰 、 5’-三磷酸腺苷 作用下， 以93%的产率得到L-fuculose 1-phosphate
  参考文献：
  名称：

  Efficient enzymatic synthesis of l -rhamnulose and l -fuculose

  摘要：

  L-Rhamnulose (6-deoxy-L-arabino-2-hexulose) and L-fuculose (6-deoxy-L-lyxo-2-hexulose) were prepared from L-rhamnose and L-fucose by a two-step strategy. In the first reaction step, isomerization of L-rhamnose to L-rhamnulose, or L-fucose to L-fuculose was combined with a targeted phosphorylation reaction catalyzed by L-rhamnulose kinase (RhaB). The by-products (ATP and ADP) were selectively removed by silver nitrate precipitation method. In the second step, the phosphate group was hydrolyzed to produce L-rhamnulose or L-fuculose with purity exceeding 99% in more than 80% yield (gram scale). (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.12.051

文献信息

• Structural characterization of an L-fuculose-1-phosphate aldolase from Klebsiella pneumoniae
  作者：Xiaorui Lou、Jianyu Zhang、Shimeng Liu、Runhao Wang、Weiping Li、Ruihua Liu、Qionglin Zhang、Mark Bartlam

  DOI：10.1016/j.bbrc.2022.03.127

  日期：2022.6

  Fuculose phosphate aldolases play an important role in glycolysis and gluconeogenesis pathways. L-fuculose 1-phosphate aldolase catalyzes the reversible cleavage of L-fuculose 1-phosphate to DHAP and L-lactaldehyde. Class II aldolases found in bacteria are linked to pathogenesis of human pathogens, and have potential applications in the biosynthesis of carbohydrates and other chiral compounds. Here

  岩藻糖磷酸醛缩酶在糖酵解和糖异生途径中发挥重要作用。L-岩藻糖 1-磷酸醛缩酶催化 L-岩藻糖 1-磷酸可逆地裂解为 DHAP 和 L-乳醛。在细菌中发现的 II 类醛缩酶与人类病原体的发病机制有关，并且在碳水化合物和其他手性化合物的生物合成中具有潜在的应用。在这里，我们报告了来自医院病原体肺炎克雷伯菌的推定 L-岩藻糖 1-磷酸醛缩酶 ( Kp FucA)的结构，分辨率为 1.85 Å。该酶在空间群 P422 中结晶，每个不对称单元有一个单体。分析超速离心分析证实KpFucA 是溶液中的四聚体。在活性口袋中鉴定出镁离子辅因子和硫酸根离子。酶活性测定证实，Kp FcuA 对 L-岩藻糖 1-磷酸作为底物具有强烈的偏好，但也可以催化 1,6-二磷酸果糖和 6-磷酸葡萄糖的裂解。这项工作应该为进一步研究Kp FucA 在肺炎克雷伯菌发病机制或工业应用中的作用提供一个起点。
• Fessner, Wolf-Dieter; Sinerius, Gudrun; Schneider, Achim, Angewandte Chemie, 1991, vol. 103, # 5, p. 596 - 599
  作者：Fessner, Wolf-Dieter、Sinerius, Gudrun、Schneider, Achim、Dreyer, Matthias、Schulz, Georg E.、et al.

  DOI：——

  日期：——
• IMPERIALI, BARBARA;ZIMMERMAN, JANET WARREN, TETRAHEDRON LETT., 31,(1990) N5, C. 6485-6488
  作者：IMPERIALI, BARBARA、ZIMMERMAN, JANET WARREN

  DOI：——

  日期：——
• Enzymic Synthesis of L-Fucose and Analogs
  作者：Chi-Huey Wong、Ramon Alajarin、Francisco Moris-Varas、Olga Blanco、Eduardo Garcia-Junceda

  DOI：10.1021/jo00127a052

  日期：1995.11
• Efficient enzymatic synthesis of l -rhamnulose and l -fuculose
  作者：Liuqing Wen、Lanlan Zang、Kenneth Huang、Shanshan Li、Runling Wang、Peng George Wang

  DOI：10.1016/j.bmcl.2015.12.051

  日期：2016.2

  L-Rhamnulose (6-deoxy-L-arabino-2-hexulose) and L-fuculose (6-deoxy-L-lyxo-2-hexulose) were prepared from L-rhamnose and L-fucose by a two-step strategy. In the first reaction step, isomerization of L-rhamnose to L-rhamnulose, or L-fucose to L-fuculose was combined with a targeted phosphorylation reaction catalyzed by L-rhamnulose kinase (RhaB). The by-products (ATP and ADP) were selectively removed by silver nitrate precipitation method. In the second step, the phosphate group was hydrolyzed to produce L-rhamnulose or L-fuculose with purity exceeding 99% in more than 80% yield (gram scale). (C) 2015 Elsevier Ltd. All rights reserved.