3-(羟基甲基)赤藓糖醇 | 10592-17-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 3-(羟基甲基)赤藓糖醇
• 英文名称: (3S)-2-hydroxymethylbutane-1,2,3,4-tetrol
• 英文别名: 3-C-(hydroxymethyl)erythritol；apiitol；D-apiitol；(3S)-2-(hydroxymethyl)butane-1,2,3,4-tetrol
• CAS: 10592-17-3
• 化学式: C₅H₁₂O₅
• 分子量: 152.147
• InChiKey: SDXWEZQDLHNYFR-BYPYZUCNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.2
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  101
• 氢给体数：
  5
• 氢受体数：
  5

安全信息

• 海关编码：
  2905499000

反应信息

• 作为反应物：
  描述：

  3,4,5-tris(benzyloxy)benzoyl chloride 、 3-(羟基甲基)赤藓糖醇 在 吡啶 作用下， 反应 12.0h， 以90%的产率得到(+)-(S)-3-hydroxy-3-(((3,4,5-tris(benzyloxy)benzoyl)oxy)methyl)butane-1,2,4-triyl tris(3,4,5-tris(benzyloxy)benzoate)
  参考文献：
  名称：

  （+）-和（-）-1,3,4,5-四没食子酰基apiitol的总合成和天然存在的（-）-1,3,4,5-四没食子酰基apiitol的绝对构型的修订

  摘要：

  （+）-和（-）-1,3,4,5-四没食子基apiitol的总合成分别从d-核糖和1-核糖分七个步骤完成。由两种对映体的旋光度与天然产物，绝对构型的在C-3中天然存在的1,3,4,5- tetragalloylapiitol比较已被修改为- [R 。合成的（+）-和（-）-1,3,4,5-四没食子酰基apiitol中C-3的绝对构型通过圆二色性激子手性方法进一步证实。

  DOI：

  10.1016/j.tet.2011.08.088
• 作为产物：
  描述：

  D-apiose 在 ammonium hydroxide 、 sodium tetrahydroborate 作用下， 反应 1.5h， 生成 3-(羟基甲基)赤藓糖醇
  参考文献：
  名称：

  The detection and quantification of apiose by capillary gas chromatography of its alditol acetates

  摘要：

  DOI：

  10.1016/0008-6215(92)85085-e

文献信息

• Synthesis of 3-C-(hydroxymethyl)erythritol and 3-C-methylerythritol
  作者：Zbigniew J. Witczak、Roy L. Whistler、James R. Daniel

  DOI：10.1016/0008-6215(84)85201-5

  日期：1984.10

  3-C-(Hydroxymethyl)erythritol was prepared from 3-C-(hydroxymethyl)-2,3-O-isopropylidene-D-erythro-tetrofuranose (4) by hydrolysis followed by reduction, or by reduction followed by hydrolysis. Monotosylation of 4, followed by reduction with lithium aluminum hydride and hydrolysis, afforded 3-C-methylerythritol.

  由3-C-（羟甲基）-2,3-O-异亚丙基-D-赤型-四呋喃糖（4）通过水解然后还原，或通过还原然后水解来制备3-C-（羟甲基）赤藓糖醇。4的单甲苯磺酰化，然后用氢化铝锂还原并水解，得到3-C-甲基赤藓糖醇。
• New Hemiterpenoid Pentol and Monoterpenoid Glycoside of Torillis japonica Fruit, and Consideration of the Origin of Apiose.
  作者：Junichi KITAJIMA、Nobuyuki SUZUKI、Toru ISHIKAWA、Yasuo TANAKA

  DOI：10.1248/cpb.46.1583

  日期：——

  From the water-soluble portion of Torillis japonica D.C. fruit, a new hemiterpenoid pentol, (3R)-2-hydroxymethylbutane-1, 2, 3, 4-tetrol (1) and a new monoterpenoid apiosyl-glucoside (4) have been isolated together with known (2S, 3R)-2-methylbutane-1, 2, 3, 4-tetrol (2) and hemiterpenoid glucoside (3).As 2 is a commonly existing constituent in Umbellierous plants, and considered to be the first putative precursor of isoprenoid derived from glucose, we assumed that apiose and these hemiterpenoids may be biosynthesized from glucose by a mevalonate-independent route of isoprenoid.

  从 Torillis japonica D.C. 果实的水溶性部分中，分离出一种新的半萜五醇、(3R)-2-羟甲基丁烷-1,2,3,4-四醇 (1) 和一种新的单萜芹基葡萄糖苷 (4)与已知的 (2S, 3R)-2-甲基丁烷-1, 2, 3, 4-四醇 (2) 和半萜糖苷 (3) 一起。As 2 是伞形科植物中常见的成分，被认为是第一个假定的成分由于类异戊二烯是从葡萄糖衍生的类异戊二烯的前体，我们假设芹菜糖和这些半萜类化合物可能是通过不依赖甲羟戊酸的类异戊二烯途径从葡萄糖生物合成的。
• The acetylation of apiitol in the determination of apiose
  作者：Paul K. Kindel、Liang Cheng

  DOI：10.1016/0008-6215(90)84092-9

  日期：1990.5

  tetraacetate] by gas-liquid chromatography and mass spectrometry. In N,N-dimethylformamide, with 1-methylimidazole as catalyst, the acetylation of apiitol was essentially complete in 4 h at 85 degrees, and the formation of methylthiomethyl ether was avoided. A method for preparing alditol acetates using 1-methylimidazole as the catalyst, and suitable for samples containing apiose as well as ordinary sugars

  当使用120度乙酸酐和乙酸钠作为催化剂时，apiitol的完全乙酰化需要9小时。在乙酰化完成之前，检测到了apiitol五乙酸酯和apiitol四乙酸酯。当反应在二甲基亚砜中，以1-甲基咪唑为催化剂时，观察到第三种化合物，并鉴定为1,2,4-三-O-乙酰基-3-C-（乙酰氧基甲基）-3-O-通过气-液色谱法和质谱法测定（甲基硫代甲基）-D-甘油-tritritol [3-O-（甲基硫代甲基）apiitol四乙酸酯]。在以1-甲基咪唑为催化剂的N，N-二甲基甲酰胺中，apiitol的乙酰化在85度下4小时内基本完成，避免了甲硫基甲基醚的形成。一种以1-甲基咪唑为催化剂制备醛糖醇乙酸酯的方法，并且描述了适用于含有apiose以及普通糖的样品的方法。证明通过气液色谱法很难将木糖醇五乙酸酯从五乙酸木糖醇中分离出来。但是，实际上可以将芹菜素醇和木糖醇的过乙酸完全分离，而将鼠李糖醇，果糖醇，阿拉伯糖醇
• <scp>d</scp> -Apiose Reductase from <i>Aerobacter aerogenes</i>
  作者：Donna L. Neal、Paul K. Kindel

  DOI：10.1128/jb.101.3.910-915.1970

  日期：1970.3

  A strain of Aerobacter aerogenes PRL-R3 has been isolated which utilizes d -apiose as its sole source of carbon. A new enzyme, d -apiose reductase, was discovered in this strain. The enzyme was not present when the strain was grown on d -glucose. d -Apiose reductase catalyzes the nicotinamide adenine dinucleotide-dependent interconversion of d -apiose and d -apiitol. The enzyme is specific for d -apiose and d -apiitol, with a few possible exceptions. The K _m for d -apiose is 0.02 m . The K _m for d -apiitol is 0.01 m . The enzyme is almost completely specific for the reduced and oxidized forms of nicotinamide adenine dinucleotide. When cell-free extracts were centrifuged at 100,000 × g for 1 hr, the enzyme remained in solution. Optimal activity for the reduction of d -apiose was obtained at p H 7.5 in glycylglycine buffer, whereas for the oxidation of d -apiitol it was obtained at p H 10.5 in glycine buffer. Enzymatic reduction of d -apiose was not appreciably affected by the presence of 0.02 m ethylenediaminetetraacetate. Paper chromatography and specific spray reagents were used to identify d -apiitol and d -apiose as the products of this reversible reaction. d -Apiose and d -apiitol did not serve as substrates for ribitol dehydrogenase and d -arabitol dehydrogenase from A. aerogenes PRL-R3.

  一株利用d-阿皮酮作为唯一碳源的气生芽孢杆菌PRL-R3菌株已经被分离出来。在该菌株中发现了一种新的酶，d-阿皮酮还原酶。当该菌株在d-葡萄糖上生长时，该酶不存在。d-阿皮酮还原酶催化以烟酰胺腺嘌呤二核苷酸为依托的d-阿皮酮和d-阿皮醇之间的相互转化。该酶对d-阿皮酮和d-阿皮醇具有特异性，但也有一些例外。d-阿皮酮的Km为0.02m，d-阿皮醇的Km为0.01m。该酶对烟酰胺腺嘌呤二核苷酸的还原和氧化形式具有几乎完全的特异性。当细胞提取物以100,000×g离心1小时时，该酶仍然溶解在溶液中。在甘氨酰甘氨酸缓冲液中，d-阿皮酮还原的最佳活性在pH 7.5处获得，而在甘氨酸缓冲液中，d-阿皮醇氧化的最佳活性在pH 10.5处获得。存在0.02m乙二胺四乙酸对d-阿皮酮的酶促还原作用影响不大。使用纸层析和特异性喷雾试剂鉴定了d-阿皮醇和d-阿皮酮是该可逆反应的产物。d-阿皮酮和d-阿皮醇不是气生芽孢杆菌PRL-R3菌株中的核糖醇脱氢酶和阿拉伯糖醇脱氢酶的底物。
• An HIV RNase H Inhibitory 1,3,4,5-Tetragalloylapiitol from the African Plant <i>Hylodendron gabunensis</i>
  作者：Kentaro Takada、Alun Bermingham、Barry R. O’Keefe、Antony Wamiru、John A. Beutler、Stuart F. J. Le Grice、John Lloyd、Kirk R. Gustafson、James B. McMahon

  DOI：10.1021/np0702279

  日期：2007.10.1

  A new compound, 1,3,4,5-tetragalloylapiitol (1), was isolated from the aqueous extract of the plant Hylodendron gabunensis and was found to be a potent inhibitor of RNase H enzymatic activity. The structure of 1 was elucidated by NMR analyses to be an apiitol (2) sugar moiety substituted with four gallic acid residues. Optical rotation measurements of the free sugar following basic hydrolysis indicated that the 3S absolute configuration was the same as that Of D-apiitol. Compound I inhibited HIV-1, HIV-2, and human RNase H with IC50 values of 0.24, 0.13, and 1.5 mu M, respectively, but it did not show inhibition of E. coli RNase H at 10 mu M.