L-rhamnulose 1-phosphate | 444-09-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: L-rhamnulose 1-phosphate
• 英文别名: [(3R,4S,5S)-3,4,5-trihydroxy-2-oxohexyl] dihydrogen phosphate
• CAS: 444-09-7
• 化学式: C₆H₁₃O₈P
• 分子量: 244.138
• InChiKey: KNYGWWDTPGSEPD-FUTKDDECSA-N

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-rhamnulose 1-phosphate 在 盐酸 、 acid phosphatase from Escherichia coli 、 magnesium 、 锌 作用下， 以 水 为溶剂， 以82%的产率得到L-rhamnulose
  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
• 作为产物：
  描述：

  L-鼠李糖 在 L-rhamnose isomerase from Escherichia coli 、 L-rhamnulose kinase from Thermotoga maritima MSB₈ 、 magnesium 、 锰 、 5’-三磷酸腺苷 作用下， 以91%的产率得到L-rhamnulose 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

• Borate as a Phosphate Ester Mimic in Aldolase-Catalyzed Reactions: Practical Synthesis ofL-Fructose andL-Iminocyclitols
  作者：Masakazu Sugiyama、Zhangyong Hong、Lisa J. Whalen、William A. Greenberg、Chi-Huey Wong

  DOI：10.1002/adsc.200600356

  日期：2006.12

  Dihydroxyacetone phosphate (DHAP)-dependent aldolases have been widely used for the organic synthesis of unnatural sugars or derivatives. The practicality of using DHAP-dependent aldolases is limited by their strict substrate specificity and the high cost and instability of DHAP. Here we report that the DHAP-dependent aldolase L-rhamnulose 1-phosphate aldolase (RhaD) accepts dihydroxyacetone (DHA)

  磷酸二羟基丙酮（DHAP）依赖性醛缩酶已广泛用于非天然糖或衍生物的有机合成。使用依赖DHAP的醛缩酶的实用性受到其严格的底物特异性以及DHAP的高成本和不稳定性的限制。在这里我们报告依赖DHAP的醛缩酶L-鼠李糖1-磷酸醛缩酶（RhaD）在硼酸盐缓冲液的存在下接受二羟基丙酮（DHA）作为供体底物，大概是通过原位可逆的形成DHA硼酸酯。该反应似乎是不可逆的，热力学上将产物捕获为硼酸盐配合物。我们已经将该发现用于开发非热量甜味剂L-果糖的实用一步合成。在RhaD存在下，由消旋甘油醛和DHA合成L-果糖，硼酸盐的克收率为92％。我们还分两步合成了一系列L-亚氨基环糖醇，它们是潜在的糖苷酶抑制剂。
• 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：——
• 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.