D-apiose | 639-97-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: D-apiose
• 英文别名: D-apiofuranose；L-Apiose；(3R,4R)-4-(hydroxymethyl)oxolane-2,3,4-triol
• CAS: 639-97-4
• 化学式: C₅H₁₀O₅
• 分子量: 150.131
• InChiKey: ASNHGEVAWNWCRQ-LJJLCWGRSA-N

物化性质

• 比旋光度：
  D15 +5.6°; D19 +9.1°
• 沸点：
  368.8±35.0 °C(Predicted)
• 密度：
  1.518±0.06 g/cm3(Predicted)
• 溶解度：
  DMSO（微溶）、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  -2.2
• 重原子数：
  10
• 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：

  D-apiose 在 N-甲基咪唑 、 ammonium hydroxide 、 sodium tetrahydroborate 作用下， 以 水 为溶剂， 反应 1.67h， 生成 apiitol 1,2,4,4'-tetraacetate
  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
• 作为产物：
  描述：

  (3S,5R,6S,9R)-megastigmane-3,9-diol 3-O-β-D-(6'-O-β-D-apiofuranosyl)glucopyranoside 在 盐酸 、 水 作用下， 反应 1.0h， 生成 D-apiose
  参考文献：
  名称：

  Oblongionosides A–F, megastigmane glycosides from the leaves of Croton oblongifolius Roxburgh

  摘要：

  From the 1-BuOH-soluble fraction of a MeOH extract of the leaves of Croton oblongifolius Roxburgh, collected in Chiang Mai, Thailand, six megastigmane glycosides, named oblongionosides A-F were isolated together with eight known compounds, and their structures elucidated on the basis of spectroscopic data. Absolute structures were determined by HPLC analyses and application of the modified Mosher's method. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2012.05.011

文献信息

• Steroid saponins and sapogenins of underground parts of Trillium kamtschaticum Pall. IV. Additional oligoglycosides of 18-norspirostane derivatives and other steroidal constituents.
  作者：NAOMICHI FUKUDA、NARIKO IMAMURA、EIKO SAITO、TOSIHIRO NOHARA、TOSHIO KAWASAKI

  DOI：10.1248/cpb.29.325

  日期：——

  Three oligoglycosides of 18-norspirostane derivatives, Ty-2, Ty-3, and Ty-4, along with two steroidal compounds, Tm and Tj, were isolated from the underground parts of Trillium kamtschaticum PALL. These five compounds and two other compounds, Th and Tz acetate, which had been obtained previously but remained unidentified, were characterized as follows. Ty-2, mp 235-240°(dec.), [α]D-110° : deapio-trillenoside A (II) (named trillenoside B). Ty-3, mp 182-185°(dec.), [α]D-98.7° : 3, 21-di-O-acetyl-24-epitrillenogenin 1-O-(2', 3', 4'-tri-O-acetyl-α-L-rha·pyr)-(1-2)-α-L-ara·pyranoside (IV) (epitrillenoside C-PA). Ty-4, mp 226-230°(dec.), [α]D-105°; 21-deoxytrillenoside A (VII) (deoxytrillenoside A). Tm, mp 326-329°(dec.), [α]D-99.4° : 24β-hydroxypennogenin (V). Tj, mp 205-212°(dec.), [α]D-66.5° : prototype compound (VIII) of pennogenin 3-O-β-chacotrioside. Th, mp 194-200°(dec.), [α]D-90° : prototype compound (IX) of pennogenin 3-O-α-L-rha·pyr-β-chacotrioside. Tz acetate : crude ecdysterone triacetate (X). This is the first report of the natural occurrence of these compounds, except for IX and X ; the occurrence of IV is particularly interesting. VIII and IX had been expected to coexist with the corresponding pennogenin glycosides.

  从延龄草地下部分分离得到3个18-去甲螺旋甾烷衍生物三糖甙Ty-2、Ty-3和Ty-4及2个甾体化合物Tm和Tj。以前得到的但是未被鉴定的2个甾体化合物Th和Tz乙酸酯也可被鉴定。其鉴定结果如下:Ty-2,熔点235-240°(分解),[α]_D-110°:异延龄草皂甙A (Ⅱ) (延龄草皂甙B)。Ty-3,熔点182-185°(分解),[α]_D-98.7°:3,21-二-O-乙酰基-24-表延龄皂甙元1-O-(2′, 3′, 4′-三-O-乙酰基-α-L-吡喃鼠李糖)-(1→2)-α-L-吡喃阿拉伯糖甙 (Ⅳ) (表延龄草皂甙C-PA)。Ty-4,熔点226-230°(分解),[α]_D-105°:21-去氧延龄草皂甙A (Ⅶ) (去氧延龄草皂甙A)。Tm,熔点326-329°(分解),[α]_D-99.4°:24β-羟基蚱蜢甾酮 (Ⅴ)。Tj,熔点205-212°(分解),[α]_D-66.5°:蚱蜢甾酮3-O-β-查可三糖甙原型化合物 (Ⅷ)。Th,熔点194-200°(分解),[α]_D-90°:蚱蜢甾酮3-O-α-L-吡喃鼠李糖-β-查可三糖甙原型化合物 (Ⅸ)。Tz乙酸酯:乙基蜕皮甾酮三乙酸酯粗品 (Ⅹ)。除了化合物Ⅸ、Ⅹ以外,其它化合物在自然界中的发现尚属首次。特别是化合物Ⅳ的出现引起了人们极大的兴趣。在此之前人们曾预测在相应的蚱蜢甾酮糖甙中共存Ⅷ和Ⅸ型化合物。
• New saponins from<i>Sechium mexicanum</i>
  作者：Beatriz Hernández-Carlos、Miriam Carmona-Pineda、Claudia Villanueva-Cañongo、Jesús F. López-Olguín、Agustín Aragón-García、Pedro Joseph-Nathan

  DOI：10.1002/mrc.2487

  日期：2009.11

  The chemical study of Sechium mexicanum roots led to the isolation of the two new saponins 3-O-beta-D-glucopyranosyl (1 --> 3)-beta-D-glucopyranosyl-2beta,3beta,16alpha,23-tetrahydroxyolean-12-en-28-oic acid 28-O-alpha-L-rhamnopyranosyl-(1 --> 3)-beta-D-xylopyranosyl-(1 --> 4)-alpha-L-rhamnopyranosyl-(1 --> 2)-alpha-L-arabinopyranoside} (1) and 3-O-beta-D-glucopyranosyl (1 --> 3)-beta-D-glucopyranosyl-2beta

  3）-β-D-吡喃并吡喃糖基-（1-> 4）-α-L-鼠李糖基吡喃糖基-（1-> 2）-α-L-阿拉伯吡喃糖苷}（3），炸药苷A（1）（4）和B（3）（5）。通过结合使用（1）H和（13）C 1D-NMR，COSY，TOCSY，gHMBC和gHSQC 2D-NMR以及天然化合物及其过乙酰化衍生物的FABMS来阐明皂苷1和2的结构如通过化学降解。化合物1-3是在Sechium属中发现的含有聚没食子酸和16-羟基原酸的皂苷的第一个实例，而现在已经详细地表征了已经通过NMR部分表征的4和5的皂苷。天然化合物及其过乙酰化衍生物的gHMBC和gHSQC 2D-NMR和FABMS，以及通过化学降解的方法。化合物1-3是在Sechium属中发现的含有聚没食子酸和16-羟基原酸的皂苷的第一个实例，而现在已经详细地表征了已经通过NMR部分表征的4和5的皂苷。天然化合物及其过乙酰化衍生物的gHMBC和gHSQC
• Apioglycyrrhizin and araboglycyrrhizin, two new sweet oleanene-type triterpene oligoglycosides from the root of Glycyrrhiza inflata.
  作者：Isao KITAGAWA、Masahiro SAKAGAMI、Fumi HASHIUCHI、Jun Liang ZHOU、Masayuki YOSHIKAWA、Jiali REN

  DOI：10.1248/cpb.37.551

  日期：——

  Two new sweet oleanene-type triterpene oligoglycosides, named apioglycyrrhizin and araboglycyrrhizin, were isolated from the air-drie root of Glycyrrhiza inflata [Chinese Glycyrrhizae Radix, Shinkyo-kanzo in Japanese], and their structures have been determined on the basis of chemical and physicochemical evidence.

  从胀果甘草（中药名为甘草，日文名为新娇甘）的干燥根中分离出两种新的甘遂型三萜寡糖苷，分别命名为芹菜苷甘草酸和阿拉伯苷甘草酸，并通过化学和物理化学证据确定了它们的结构。
• An efficient and versatile synthesis of apiose and some C-1-aldehyde- and/or 2,3-O-protected derivatives
  作者：Miroslav Koóš、Júlia Mičová、Bohumil Steiner、Juraj Alföldi

  DOI：10.1016/s0040-4039(02)01084-5

  日期：2002.7

  The synthesis of 2,3-O-isopropylidene-β-d-apiofuranose (58% overall yield) from l-arabinose via 3-C-(hydroxymethyl)-2,3-O-isopropylidene-d-glycero-tetrose diethyl dithioacetal is reported. Starting from l-arabinose an alternative precursor of d-apiose, 3-C-(hydroxymethyl)-2,3-O-isopropylidene-d-glycero-tetrose dimethyl acetal, was prepared from 2,3-O-isopropylidene-l-threo-tetrodialdose dimethyl acetal

  通过3- C-（羟甲基）-2,3 - O-异亚丙基-d-甘油-四糖二乙基二硫缩醛由1-阿拉伯糖合成2,3 - O-异亚丙基-β-d-呋喃呋喃糖（总收率58％）被报道。从1-阿拉伯糖开始，由2，3 - O-异亚丙基-1- β制备d-apiose的另一种前体，即3- C-（羟甲基）-2，3 - O-异亚丙基-d-甘油-蔗糖二甲基乙缩醛。苏-tetrodialdose二甲基乙缩醛和醛醇缩合-坎尼扎罗反应的甲醛。酸水解时，两种前体都可以得到未保护的d-apiose。
• Efficient chemoenzymatic synthesis of 4-nitrophenyl β-d-apiofuranoside and its use in screening of β-d-apiofuranosidases
  作者：Peter Kis、Elena Potocká、Vladimír Mastihuba、Mária Mastihubová

  DOI：10.1016/j.carres.2016.04.030

  日期：2016.7

  4-Nitrophenyl β-d-apiofuranoside as a chromogenic probe for detection of β-d-apiofuranosidase activity was prepared in 61% yield from 2,3-isopropylidene-α,β-d-apiofuranose through a sequence of five reactions. The synthesis involves one regioselective enzymatic step-benzoylation of primary hydroxyl of 2,3-isopropylidene-α,β-d-apiofuranose catalysed by Lipolase 100T and stereoselective β-d-apiofuranosylation

  通过五个反应序列，由2,3-异亚丙基-α，β-d-呋喃呋喃糖以61％的收率制备了4-硝基苯基β-d-呋喃呋喃糖苷作为检测β-d-呋喃糖苷酶活性的生色探针。合成涉及一种由Lipolase 100T催化的2,3-异亚丙基-α，β-d-呋喃呋喃糖伯羟基的区域选择性酶促步骤苯甲酰化和使用BF3·OEt2 / Et3N的对硝基苯酚的立体选择性β-d-呋喃呋喃糖基化。该产物用于筛查61种粗制商业酶和植物材料样品中的β-d-apiofuranosidase活性。源自曲霉属不同菌株的十五种酶制剂显示出β-d-呋喃呋喃糖苷酶活性。在Rapidase AR 2000（78.27 U / g）和冻干的Viscozyme L（64,36 U / g）中发现了最高的活性。