3-脱氧-D-甘油-D-乳-2-吡喃壬酮糖酸 | 153666-19-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 3-脱氧-D-甘油-D-乳-2-吡喃壬酮糖酸
• 英文名称: ketodeoxynonulosonic acid
• 英文别名: 2-keto-3-deoxy-nonulosonic acid；2-keto-3-deoxynononic acid；2-keto-3-deoxy-D-glycero-D-galacto-nonulosonic acid；keto deeoxy nonanoic acid；2-keto-3-deoxy-D-glycero-β-D-galacto-2-nonulosonic acid；KDN；Keto-Deoxy-Nonulonic acid；(4S,5R,6R)-2,4,5-trihydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
• CAS: 153666-19-4
• 化学式: C₉H₁₆O₉
• 分子量: 268.221
• InChiKey: CLRLHXKNIYJWAW-QBTAGHCHSA-N

物化性质

• 熔点：
  26-28?C
• 沸点：
  726.8±60.0 °C(Predicted)
• 密度：
  1.860±0.06 g/cm3(Predicted)
• 溶解度：
  DMF：10mg/mL； DMSO：30mg/mL； PBS（pH 7.2）：10 mg/mL

计算性质

• 辛醇/水分配系数(LogP)：
  -3.5
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  168
• 氢给体数：
  7
• 氢受体数：
  9

安全信息

• 安全说明：
  S22,S24/25
• WGK Germany：
  3
• 储存条件：
  -20°C

反应信息

• 作为反应物：
  描述：

  3-脱氧-D-甘油-D-乳-2-吡喃壬酮糖酸 生成 azane;(4S,5R,6R)-2,4,5-trihydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
  参考文献：
  名称：

  NAKAMURA, MITSUNOBU;FURUHATA, KIMIO;OGURA, HARUO, CHEM. AND PHARM. BULL., 36,(1988) N2, C. 4807-4813

  摘要：

  DOI：
• 作为产物：
  描述：

  2,3:5,6-二-O-异亚丙基-D-甘露糖酸-1,4-内酯 在 sodium tetrahydroborate 、 N-溴代丁二酰亚胺(NBS) 、 臭氧 、 silver nitrate 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 、 二甲基硫 、 水 、 丙酮 、 甲苯 为溶剂， 反应 65.0h， 生成 3-脱氧-D-甘油-D-乳-2-吡喃壬酮糖酸
  参考文献：
  名称：

  Practical Synthesis of 2-Keto-3-deoxy-d-glycero-d-galactononulosonic Acid (KDN)

  摘要：

  Reaction of propargylmagnesium bromide with 2,3;5,6-di-O-Isopropylidene-D-mannonolactone followed by highly stereoselective reduction of the so-formed lactol with sodium borohydride gives a syn-diol from which practical syntheses of 2-keto-3-deoxy-D-glycero-D-galactononulosonic acid (KDN) and various partially protected derivatives have been achieved all of which feature the oxidative unmasking of the alpha-keto acid moiety from the alkyne.

  DOI：

  10.1021/ol202773t

文献信息

• Diastereoselective One-Step Synthesis of 2-Keto-3-deoxy-<scp>d</scp>- glycero-<scp>d</scp>-galacto-nononic acid (KDN) Analogues as Templates for the Development of Influenza Drugs
  作者：Pedro Laborda、Su-Yan Wang、Ai-Min Lu、Meng He、Xu-Chu Duan、Ying-Juan Qian、Yong-Sam Jung、Li Liu、Josef Voglmeir

  DOI：10.1002/adsc.201700678

  日期：2017.9.18

  Novel sialic acid scaffolds have great significance in the development of influenza neuraminidase inhibitors. Here the enzymatic synthesis of a wide range of 2‐keto‐3‐deoxy‐d‐glycero‐d‐galacto‐nononic acid (KDN) analogues via aldol addition of pyruvate to d‐mannose, d‐glucose, d‐galactose, 2‐deoxy‐d‐glucose, d‐arabinose, l‐arabinose and l‐rhamnose using a previously unstudied N‐acetylneuraminic acid

  新型唾液酸支架在流感神经氨酸酶抑制剂的开发中具有重要意义。这里广泛的2-酮-3-脱氧的酶促合成d -glycero- d半乳- nononic酸（KDN）类似物通过醛醇加成的丙酮酸至d甘露糖，ð葡萄糖，ð半乳糖，2- -deoxy- d葡萄糖，d -arabinose，升-arabinose和升鼠李糖利用先前未研究ñ -acetylneuraminic神经氨酸（Neu5Ac）醛缩酶从细菌衍生Dyadobacter Fermentas公司被举例说明。几种合成的KDN类似物对突变的流感神经氨酸酶显示出与未研究的Neu5Ac相当或更好的抑制活性（A / California / 04/2009和A / Anhui / 1/2005），两者均显示出对基于Neu5Ac的神经氨酸酶抑制剂的抗性，这表明这些化合物是开发抗流感药物的有希望的模板。
• Recombinant Snail Sialic Acid Aldolase is Promiscuous towards Aliphatic Aldehydes
  作者：Zi‐Xuan Hu、Cheng Cheng、Yu‐Qian Li、Xiao‐Han Qi、Ting Wang、Li Liu、Josef Voglmeir

  DOI：10.1002/cbic.202200074

  日期：2022.7.5

  Aldolases reversibly catalyze the cleavage of carbon-carbon bonds. A recombinant snail sialic acid aldolase (sNPL) differs significantly in its carbohydrate substrate promiscuity from other sialic aldolases described so far. In addition, sNPL was able to synthesize a series of 4-hydroxy-2-oxoates using the corresponding aliphatic aldehyde substrates.

  醛缩酶可逆地催化碳-碳键的断裂。重组蜗牛唾液酸醛缩酶 (sNPL) 在其碳水化合物底物混杂性方面与迄今为止描述的其他唾液酸醛缩酶显着不同。此外，sNPL 能够使用相应的脂肪醛底物合成一系列 4-羟基-2-氧酸盐。
• PRODUCTION OF OLIGOSACCHARIDE MIXTURES BY A CELL
  申请人：Inbiose N.V.

  公开号：EP3954769A1

  公开（公告）日：2022-02-16

  The present invention is in the technical field of synthetic biology and metabolic engineering. More particularly, the present invention is in the technical field of fermentation of metabolically engineered cells. The present invention provides a method for the production of a mixture of at least two different oligosaccharides by a cell as well as the purification of at least one of said oligosaccharides from the cultivation. In addition, the present invention provides a method for the production of a mixture of at least two different oligosaccharides by a metabolically engineered cell as well as the purification of at least one of said oligosaccharides from the cultivation.

  本发明属于合成生物学和代谢工程技术领域。更具体地说，本发明属于代谢工程细胞发酵技术领域。本发明提供了一种细胞生产至少两种不同低聚糖混合物的方法，以及从培养物中纯化至少一种所述低聚糖的方法。此外，本发明还提供了一种通过代谢工程细胞生产至少两种不同低聚糖混合物以及从培养物中纯化至少一种所述低聚糖的方法。
• Redox-Controlled Site-Specific α2–6-Sialylation
  作者：Na Lu、Jinfeng Ye、Jiansong Cheng、Aniruddha Sasmal、Chang-Cheng Liu、Wenlong Yao、Jun Yan、Naazneen Khan、Wen Yi、Ajit Varki、Hongzhi Cao

  DOI：10.1021/jacs.9b00044

  日期：2019.3.20

  The first bacterial alpha 2-6-sialyltransferase cloned from Photobacterium damselae (Pd2,6ST) has been widely applied for the synthesis of various alpha 2-6-linked sialosides. However, the extreme substrate flexibility of Pd2,6ST makes it unsuitable for site-specific alpha 2-6-sialylation of complex substrates containing multiple galactose and/or N-acetylgalactosamine units. To tackle this problem, a general redox-controlled site-specific sialylation strategy using Pd2,6ST is described. This approach features site-specific enzymatic oxidation of galactose units to mask the unwanted sialylation sites and precisely controlling the site-specific alpha 2-6-sialylation at intact galactose or N-acetylgalactosamine units.
• SHIRAI, RYUICHI;OGURA, HARUO, TETRAHEDRON LETT., 30,(1989) N7, C. 2263-2264
  作者：SHIRAI, RYUICHI、OGURA, HARUO

  DOI：——

  日期：——