3-deoxy-D-galactose

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-deoxy-D-galactose
• 英文别名: (3R,5R,6R)-6-(hydroxymethyl)tetrahydropyran-2,3,5-triol；3-Deoxy-D-galactopyranose；(3R,5R,6R)-6-(hydroxymethyl)oxane-2,3,5-triol
• 化学式: C₆H₁₂O₅
• 分子量: 164.158
• InChiKey: RJDIFQMDPPUATQ-JDJSBBGDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  90.2
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-deoxy-D-galactose 在 calcium carbonate 、 calcium bromide 作用下， 生成 3-deoxy-D-xylo-hexonic acid
  参考文献：
  名称：

  Zinner,H. et al., Chemische Berichte, 1964, vol. 97, p. 3536 - 3540

  摘要：

  DOI：
• 作为产物：
  描述：

  methyl 3-deoxy-β-D-galactopyranoside 在 硫酸 作用下， 生成 3-deoxy-D-galactose
  参考文献：
  名称：

  Methyl 3,4-Anhydro-β-D-galactopyranoside. I. Reduction^1,2

  摘要：

  DOI：

  10.1021/jo01050a058

文献信息

• Characterisation of a Bacterial Galactokinase with High Activity and Broad Substrate Tolerance for Chemoenzymatic Synthesis of 6-Aminogalactose-1-Phosphate and Analogues
  作者：Kun Huang、Fabio Parmeggiani、Edward Pallister、Chuen-Jiuan Huang、Fang-Fang Liu、Qian Li、William R. Birmingham、Peter Both、Baptiste Thomas、Li Liu、Josef Voglmeir、Sabine L. Flitsch

  DOI：10.1002/cbic.201700477

  日期：2018.2.16

  Furnishing phosphates: A galactokinase from L. grimontii (LgGalK) has been identified and characterised; it shows broad substrate specificity towards different nucleotide phosphates and monosaccharides. This enzyme, in combination with a galactose oxidase variant was used in the chemoenzymatic synthesis of a panel of 6‐aminogalactose‐1‐phosphate analogues.

  提供磷酸盐：已经鉴定并鉴定了来自格氏乳杆菌的半乳糖激酶（LgGalK）；它对不同的核苷酸磷酸和单糖显示出广泛的底物特异性。该酶与半乳糖氧化酶变体结合在一起，用于化学酶合成6-氨基半乳糖-1-磷酸类似物。
• Studies on the Substrate Specificity of <i>Escherichia coli</i> Galactokinase
  作者：Jie Yang、Xun Fu、Qiang Jia、Jie Shen、John B. Biggins、Jiqing Jiang、Jingjing Zhao、Joshua J. Schmidt、Peng G. Wang、Jon S. Thorson

  DOI：10.1021/ol034642d

  日期：2003.6.1

  rapidly synthesize sugar phosphates. Compared with chemical synthesis, enzymatic (kinase) routes to sugar phosphates would be attractive for this application. This work focuses upon the development of a high-throughput colorimetric galactokinase (GalK) assay and its application toward probing the substrate specificity and kinetic parameters of Escherichia coli GalK. The demonstrated dinitrosalicylic

  体外糖随机化（IVG）技术取决于快速合成糖磷酸酯的能力。与化学合成相比，酶促（激酶）途径转化为糖磷酸酯对于该应用而言将是有吸引力的。这项工作专注于高通量比色半乳糖激酶（GalK）检测方法的开发及其在探测大肠杆菌GalK的底物特异性和动力学参数方面的应用。证明的二硝基水杨酸测定法也应普遍适用于多种糖加工酶。[反应：看文字]
• Total synthesis of 3-deoxy and 3,6-dideoxy-dl-hexoses
  作者：Marek Chmielewski

  DOI：10.1016/0040-4020(80)80132-3

  日期：——

  of the double bond in 2 or 7, lactonisation of the resulting aldonic acid esters followed by acetylation and chromatographical separation of γ-lactones, reduction of lactones 16–23 to lactols with disiamylborane, and acetylation of lactols to free sugars. All compounds were obtained as pure diastereomers in racemic form.

  立体异构体3-脱氧己糖的合成24 - 27和3,6-二脱氧己糖28 - 31进行报告。（E）-2，6-二羟基-己-4-烯酸丁酯（2）用作合成3-脱氧-己糖的原料。为了合成3，6-二脱氧己糖，使用（E）-2-乙酰氧基-己-4-烯酸丁酯（7）。合成过程涉及以下连续步骤：2或7中双键的顺式或反式羟基化时，所得醛糖酸的酯的内酯化，然后乙酰化和γ-内酯，还原内酯的层析分离16 - 23与disiamylborane乳醇，和乳醇的乙酰化游离糖。获得所有化合物，为外消旋形式的纯非对映异构体。
• Derivatives of methyl β-lactoside as substrates for and inhibitors of β-d-galactosidase from E. coli
  作者：Klaus Bock、Kim Adelhorst

  DOI：10.1016/0008-6215(90)84076-7

  日期：1990.7

  6'-deoxy derivatives of methyl beta-lactoside have been synthesised by deoxygenation at positions 2', 4', and 6', and the 3'-deoxy derivative was obtained by a glycosylation reaction. The 2'-O-methyl, 2'-O-benzyl, 2'-amino-2'-deoxy, and 1'-deuterio derivatives have been synthesized also. Only the 6'-deoxy and 1'-deuterio derivatives were substrates for the beta-D-galactosidase from E. coli, and the

  通过在位置2'，4'和6'上进行脱氧反应合成了甲基β-乳糖苷的2'-，4'-和6'-脱氧衍生物，并通过糖基化反应获得了3'-脱氧衍生物。还已经合成了2'-O-甲基，2'-O-苄基，2'-氨基-2'-脱氧和1'-氘代衍生物。只有6'-脱氧和1'-氘衍生物是大肠杆菌的β-D-半乳糖苷酶的底物，而2'-脱氧和2'-氨基-2'-脱氧衍生物是水解的有效抑制剂。酶生成甲基β-乳糖苷。
• Rapid Conversion of Unprotected Galactose Analogs to their Udp-Derivatives For Use in the Chemo-Enzymatic Synthesis of Unnatural Oligosaccharides
  作者：Taketo Uchiyama、Ole Hindsgaul

  DOI：10.1080/07328309808001892

  日期：1998.11

  The rapid conversion of D-galactose, its 2-deoxy, 3-deoxy, 4-deoxy and 6-deoxy derivatives and L-arabinose to their UDP-derivatives (2-7) is described. The procedure involves the in situ preparation of the per-O-trimethylsilylated glycopyranosyl iodides and their direct reaction with UDP. All six sugar nucleotides were active as substrates for beta(1-->4)-galactosyltransferase and were used to enzymatically prepare N-acetyllactosamine (8) and five of its analogs (9-13).