D-Arabinono-1,5-lactone | 73745-98-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: D-Arabinono-1,5-lactone
• 英文别名: D-arabinonolactone；arabonolactone；(3S,4R,5R)-3,4,5-trihydroxyoxan-2-one
• CAS: 73745-98-9
• 化学式: C₅H₈O₅
• 分子量: 148.116
• InChiKey: XXBSUZSONOQQGK-JJYYJPOSSA-N

物化性质

• 沸点：
  370.3±31.0 °C(Predicted)
• 密度：
  1.743±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  辛胺 、 D-Arabinono-1,5-lactone 以 甲醇 为溶剂， 反应 1.5h， 生成 N-(1-octyl)-D-arabinonamide
  参考文献：
  名称：

  关于无环糖两亲物的构象和堆积行为：N-（1-辛基）-d-阿拉伯酰胺和N-（1-十二烷基）-d-核糖酰胺的晶体结构和N-（1的超分子组装形成性质） -辛基）-d-戊烯酰胺

  摘要：

  摘要N-（1-辛基）-d-阿拉伯酰胺[空间群P2 1，a = 4.855（3）A，b = 30.45（3）A，c = 10.59（1）A，β= 94.46（图6）°显示了以不平行的方式在不对称单元中排列的两个独立分子。它们的头基和辛基链是延伸的，但分子的整体形状是不同的。以前从未见过使用醛糖酰胺在晶体中具有相互交叉的头基和低聚亚甲基尾部的堆积排列，但与葡萄糖两亲物MEGA-8的堆积排列相同。晶体中阿拉伯糖酰胺分子的堆积与以反平行排列方式结晶的其他两亲物的堆积的比较显示出类似的行为，表明这些化合物结晶的共同机理。N-（1-十二烷基）-d-核糖酰胺[空间群P1，a ＝ 4.815（2）A，b ＝ 5。464（2）A，c = 18.084（4）A，a = 81.77（2）°，β= 87.78（3）°，γ= 83.83（3）°在不对称单元中显示一个分子。它分别显示了两个从C-2至C-5和C-2至C

  DOI：

  10.1016/0008-6215(94)00260-m
• 作为产物：
  描述：

  D-阿拉伯糖酸GAMMA-内酯 在 Burkholderia multivorans ATCC 17616 amidohydrolase J_04915 作用下， 以 aq. buffer 为溶剂， 生成 D-Arabinono-1,5-lactone
  参考文献：
  名称：

  Discovery of an l-Fucono-1,5-lactonase from cog3618 of the Amidohydrolase Superfamily

  摘要：

  A member of the amidohydrolase superfamily, BmulJ_04915 from Burkholderia multivorans, of unknown function was determined to hydrolyze a series of sugar lactones: L-fiicono-1,4-lactone, n-arabino-1,4-lactone, L-xylono-1,4-lactone, D-lyxono-1,4-lactone, and L-galactono-1,4-lactone. The highest activity was shown for L-fucono-1,4-lactone with a k(cat) value of 140 s(-1) and a k(cat)/K-m value of 1.0 x 10(5) M-1 s(-1) at pH 8.3. The enzymatic product of an adjacent L-fucose dehydrogenase, BmulJ_04919, was shown to be L-fucono-1,5-lactone via nuclear magnetic resonance spectroscopy. L-Fucono-1,5-lactone is unstable and rapidly converts nonenzymatically to L-fucono-1,4-lactone. Because of the chemical instability of L-fiicono-1,5-lactone, 4-deoxy-L-fucono-1,5-lactone was enzymatically synthesized from 4-deoxy-L-fucose using L-fucose dehydrogenase. BmulJ-04915 hydrolyzed 4-deoxy-L-fucono-1,5-lactone with a k(cat) value of 990 s(-1) and a k(cat)/K-m value of 8.0 x 106 M-1 s(-1) at pH 7.1. The protein does not require divalent cations in the active site for catalytic activity. BmulJ_04915 is the second enzyme from cog3618 of the amidohydrolase superfamily that does not require a divalent metal for catalytic activity. BmulJ_04915 is the first enzyme that has been shown to catalyze the hydrolysis of either L-fucono-1,4-lactone or L-fucono-1,5-lactone. The structures of the fuconolactonase and the fucose dehydrogenase were determined by X-ray diffraction methods.

  DOI：

  10.1021/bi3015554

文献信息

• Catalytic Hydrogenation of Arabinonic Acid and Lactones to Arabitol
  作者：Lionel Fabre、Pierre Gallezot、Alain Perrard

  DOI：10.1006/jcat.2002.3567

  日期：2002.5

  Aqueous solutions (20 wt%) of arabinonic acid in equilibrium with arabinonolactones were hydrogenated on ruthenium catalysts at 100°C or lower temperatures in a batch reactor. The highest selectivity to arabitol was 98.9% at 98% conversion, with a reaction rate of 73 mmol h−1 gRu−1 at 80°C. Reaction modeling was achieved by a detailed kinetic analysis of reaction data under various reaction conditions

  在间歇反应器中在100℃或更低的温度下在钌催化剂上氢化与阿拉伯内酯平衡的阿拉伯酸的水溶液（20wt％）。在98％的转化率下，对阿拉伯糖醇的最高选择性为98.9％，反应速率为73 mmol h -1 g Ru -1在80°C下。通过在各种反应条件下对反应数据进行详细的动力学分析，可以实现反应建模。底物的转化遵循由Horiuti-Polanyi机理建立的速率方程。在碳载体上负载的小颗粒上的选择性较高，这是因为载体对钌颗粒的供电子作用，从而降低了脱羟基反应的速率，从而导致了不需要的脱氧产物。提高选择性的最重要因素是蒽醌-2-磺酸盐（A2S）的存在，这减少了脱氧产物的形成。使用最适量的A2S，在100°C下的选择性从93.6提高到96.7％。该分子充当永久性表面改性剂，因为催化剂以相同的选择性循环使用，而无需进一步添加A2S。
• Oxidative Degradation of D-Sucrose by Employing N-Bromosuccinimide as Oxidant: A Micellar Kinetic and Catalytic Study
  作者：Minu Singh

  DOI：10.1080/15533174.2012.680144

  日期：2012.10.1

  N-bromosuccinimide and fractional-order dependence on D-sucrose. Variations of mercuric acetate had an insignificant effect on reaction rate. The solvent effect revealed that negative dielectric effect. The influence of salts on the reaction rate was also studied. Succinimide and sulfuric acid inhibit the rate. The rate constant (kW), binding constants (KS+KO), and corresponding activation parameters (Ea, ΔH#, ΔS#,

  在45°C（±0.1°C）下，研究了在酸性介质存在下，N-溴代琥珀酰亚胺和表面活性剂作为催化剂对D-蔗糖的氧化作用。速率研究是在伪一级条件下进行的，其中糖比氧化剂过量。为此目的，进行了基于胶束动力学研究的机械和结构研究。动力学揭示了对N-溴琥珀酰亚胺的一阶依赖性和对D-蔗糖的分数阶依赖性。乙酸汞的变化对反应速率的影响很小。溶剂效应显示出负介电效应。还研究了盐对反应速率的影响。琥珀酰亚胺和硫酸抑制该速率。速率常数（k W），结合常数（K S + K O），并确定相应的激活参数（E a，ΔH ＃，ΔS ＃和ΔG ＃）。提出并讨论了具有相关反应动力学的详细机理。根据Berezin模型，表面活性剂的性质和表面活性剂的电荷，对存在各种表面活性剂时D-蔗糖氧化速率之间的差异进行了定性讨论。
• Micellar effect on the reaction of chromium(VI) oxidation ofD-fructose in the presence and absence of picolinic acid in aqueous media: a kinetic study
  作者：Asim K. Das、Aparna Roy、Bidyut Saha、Rajani K. Mohanty、Mahua Das

  DOI：10.1002/poc.374

  日期：2001.6

  complex participates further in the oxidation of D-fructose and ultimately is converted into the inert Cr(III)–PA complex. In the uncatalysed path, the Cr(VI)–substrate ester experiences an acid-catalysed redox decomposition (2e transfer) in the rate-determining step giving rise to the products. The uncatalysed path shows a second-order dependence on [H+] whereas the PA catalysed path shows a fractional order

  动力学和中的Cr（VI）氧化的机制d在吡啶甲酸在含水酸性介质中存在和不存在（PA）-fructose条件[下进行了研究d -fructose] Ť »[铬（VI）] Ť在不同的温度。在动力学条件下，发现在不存在PA的情况下，Cr（VI）的单体物种具有动力学活性，而在PA催化的路径中，Cr（VI）-PA络合物被认为是活性氧化剂。在这条路径中，Cr（VI）-PA络合物受到底物的亲核攻击，形成三元络合物，随后通过乙二醇裂解经历氧化还原分解，生成C 5的内酯-醛糖醛酸以及甲醛和Cr（IV）-PA络合物。初级产物甲醛进一步氧化（部分）以形成甲酸。然后，Cr（IV）-PA络合物进一步参与D-果糖的氧化，最终转化为惰性Cr（III）-PA络合物。在未催化的路径中，Cr（VI）-底物酯在速率确定步骤中经历了酸催化的氧化还原分解（2e转移），从而产生了产物。未催化的路径显示对[H + ]的二阶依赖性，而PA催化的路径显示在[H
• Discovery of an <scp>l</scp>-Fucono-1,5-lactonase from cog3618 of the Amidohydrolase Superfamily
  作者：Merlin Eric Hobbs、Matthew Vetting、Howard J. Williams、Tamari Narindoshvili、Devon M. Kebodeaux、Brandan Hillerich、Ronald D. Seidel、Steven C. Almo、Frank M. Raushel

  DOI：10.1021/bi3015554

  日期：2013.1.8

  A member of the amidohydrolase superfamily, BmulJ_04915 from Burkholderia multivorans, of unknown function was determined to hydrolyze a series of sugar lactones: L-fiicono-1,4-lactone, n-arabino-1,4-lactone, L-xylono-1,4-lactone, D-lyxono-1,4-lactone, and L-galactono-1,4-lactone. The highest activity was shown for L-fucono-1,4-lactone with a k(cat) value of 140 s(-1) and a k(cat)/K-m value of 1.0 x 10(5) M-1 s(-1) at pH 8.3. The enzymatic product of an adjacent L-fucose dehydrogenase, BmulJ_04919, was shown to be L-fucono-1,5-lactone via nuclear magnetic resonance spectroscopy. L-Fucono-1,5-lactone is unstable and rapidly converts nonenzymatically to L-fucono-1,4-lactone. Because of the chemical instability of L-fiicono-1,5-lactone, 4-deoxy-L-fucono-1,5-lactone was enzymatically synthesized from 4-deoxy-L-fucose using L-fucose dehydrogenase. BmulJ-04915 hydrolyzed 4-deoxy-L-fucono-1,5-lactone with a k(cat) value of 990 s(-1) and a k(cat)/K-m value of 8.0 x 106 M-1 s(-1) at pH 7.1. The protein does not require divalent cations in the active site for catalytic activity. BmulJ_04915 is the second enzyme from cog3618 of the amidohydrolase superfamily that does not require a divalent metal for catalytic activity. BmulJ_04915 is the first enzyme that has been shown to catalyze the hydrolysis of either L-fucono-1,4-lactone or L-fucono-1,5-lactone. The structures of the fuconolactonase and the fucose dehydrogenase were determined by X-ray diffraction methods.
• On the conformational and packing behaviour of acyclic sugar amphiphiles: The crystal structures of N-(1-octyl)-d-arabinonamide and N-(1-dodecyl)- d-ribonamide and the supramolecular assembly-forming properties of N-(1-octyl)-d-pentonamides
  作者：Christoph André、Peter Luger、Reinhard Bach、Jürgen-Hinrich Fuhrhop

  DOI：10.1016/0008-6215(94)00260-m

  日期：1995.1

  Abstract The crystal structure of N-(1- octyl)- d -arabinonamide [space group P2 1 , a=4.855(3) A , b=30.45(3) A , c=10.59(1) A , β=94.46(6)° ] shows two independent molecules arranged in an antiparallel manner in the asymmetric unit. Their head groups and octyl chains are extended, but the overall shape of the molecules is different. The packing arrangement in the crystal, with interdigitating head

  摘要N-（1-辛基）-d-阿拉伯酰胺[空间群P2 1，a = 4.855（3）A，b = 30.45（3）A，c = 10.59（1）A，β= 94.46（图6）°显示了以不平行的方式在不对称单元中排列的两个独立分子。它们的头基和辛基链是延伸的，但分子的整体形状是不同的。以前从未见过使用醛糖酰胺在晶体中具有相互交叉的头基和低聚亚甲基尾部的堆积排列，但与葡萄糖两亲物MEGA-8的堆积排列相同。晶体中阿拉伯糖酰胺分子的堆积与以反平行排列方式结晶的其他两亲物的堆积的比较显示出类似的行为，表明这些化合物结晶的共同机理。N-（1-十二烷基）-d-核糖酰胺[空间群P1，a ＝ 4.815（2）A，b ＝ 5。464（2）A，c = 18.084（4）A，a = 81.77（2）°，β= 87.78（3）°，γ= 83.83（3）°在不对称单元中显示一个分子。它分别显示了两个从C-2至C-5和C-2至C