木糖酸-1,4-内酯 | 68035-75-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 木糖酸-1,4-内酯
• 英文名称: xylonic acid-1,4-lactone
• 英文别名: L-xylono-1,4-lactone；L-xylonic acid-4-lactone；L-Xylonsaeure-4-lacton；L-Xylonsaeure-lacton；D-Xylono-lacton；(3S,4S,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-one
• CAS: 68035-75-6
• 化学式: C₅H₈O₅
• 分子量: 148.116
• InChiKey: CUOKHACJLGPRHD-NUNKFHFFSA-N

物化性质

• 熔点：
  99-103 °C
• 沸点：
  364.3±11.0 °C(Predicted)
• 密度：
  1.667±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  10
• 可旋转键数：
  1
• 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：

  木糖酸-1,4-内酯 在 ruthenium-on-carbon 氢气 作用下， 以 水 为溶剂， 以90-91 mol-%的产率得到Xylitol
  参考文献：
  名称：

  Production of xylitol

  摘要：

  一种从D-葡萄糖、D-果糖、D-半乳糖或其混合物中生产木糖醇的方法，其特征在于包括以下步骤：a.将起始物氧化成主要由L-木糖酸、D-阿拉伯糖酸、D-吕克糖酸或至少两种该酸的混合物组成的中间体，其中该酸可以是自由的或以其盐、内酯或O-甲酰衍生物的形式存在；b.将所述中间体与氢化催化剂和氢气在一个或多个步骤中处理成主要由木糖醇或木糖醇、阿拉伯糖醇和核糖醇混合物组成的产物；c.如有必要，从所述产物中分离木糖醇，并将所述阿拉伯糖醇和核糖醇的部分馏分返回到前述反应步骤b中。

  公开号：

  US05563303A1
• 作为产物：
  描述：

  L-xylopyranose 在 溴 、 potassium carbonate 作用下， 以 水 为溶剂， 生成 木糖酸-1,4-内酯
  参考文献：
  名称：

  白蛋白的合成和绝对构型分配：可见光光催化作用的后期还原脱碘†

  摘要：

  描述了白蛋白及其对映体的合成。它在后期涉及可见光光催化脱碘。天然白蛋白的绝对构型确定为（1 R，3 S）。这项工作为结构改造从旧结构开发出新型除草剂提供了基础。

  DOI：

  10.1039/c6ob00371k

文献信息

• Maillard Degradation Pathways of Vitamin C
  作者：Mareen Smuda、Marcus A. Glomb

  DOI：10.1002/anie.201300399

  日期：2013.4.26

  Degradation mechanisms: 75 % of the Maillard degradation pathways of ascorbic acid can be explained by oxidative α fragmentation (31 %), β cleavage (32 %), and decarboxylation from hydrate/hemiaminal intermediates (12 %), which lead to carbonyl and dicarbonyl compounds, carboxylic acids, and amide advanced glycation endproducts. The results are a major step forward in the understanding of changes occurring

  降解机理：抗坏血酸美拉德降解途径的75％可以通过氧化性α片段化（31％），β裂解（32％）和水合物/半缩醛中间体的脱羧作用（12％）来解释，这导致羰基和二羰基化合物，羧酸和酰胺高级糖基化终产物。该结果是在理解含维生素C的系统中发生的变化方面迈出的重要一步。
• Stereocontrolled Nucleophilic Addition to Five-Membered Oxocarbenium Ions Directed by the Protecting Groups. Application to the Total Synthesis of (+)-Varitriol and of Two Diastereoisomers Thereof
  作者：Alma Sánchez-Eleuterio、William H. García-Santos、Howard Díaz-Salazar、Marcos Hernández-Rodríguez、Alejandro Cordero-Vargas

  DOI：10.1021/acs.joc.7b01211

  日期：2017.8.18

  stereodivergent C-glycosidation of carbohydrate-derived lactones can be mediated by the protecting groups and applied to the total synthesis of (+)-varitriol and of two diastereoisomers thereof, which represent an unprecedent use of the protecting groups in the synthesis of a naturally occurring compound. In particular, the stereoselective nucleophile attack for 2,3-trans-substituted five-membered ring

  碳水化合物衍生的内酯的立体发散的C-糖基化可以由保护基团介导，并应用于（+）-varitriol及其两个非对映异构体的总合成，这代表了保护基团在天然合成中的前所未有的用途。发生的化合物。特别地，保护基团中芳环的存在强烈影响对2，3-反式取代的五元环氧碳鎓离子的立体选择性亲核体攻击。根据量子化学计算，立体选择性取决于带有环外三键的C-2保护基的芳环与氧碳鎓离子之间的π-π相互作用。这些相互作用说明了其中C-2和C-3取代基采用伪轴向取向的构象异构体的稳定性。当保护基不包含芳环时，立体化学结果取决于Woerpel模型建立的立体电子因素。基于这些发现，完成了天然产物（+）-水三酚和两种非对映异构体的简明全合成。
• 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.
• Heyns; Stein, Justus Liebigs Annalen der Chemie, 1947, vol. 558, p. 194,197
  作者：Heyns、Stein

  DOI：——

  日期：——
• Characterisation of D-Arabinono-1,4-Lactone Oxidase from Candida albicans ATCC 10231
  作者：Won-Ki Huh、Seong-Tae Kim、Kap-Seok Yang、Yeong-Jae Seok、Yung Chil Hah、Sa-Ouk Kang

  DOI：10.1111/j.1432-1033.1994.1073b.x

  日期：1994.11

  D‐Erythroascorbic acid was detected from the cell extracts of a dimorphic fungus, Candida albicans. Its concentration in yeast cells grown at 25 °C was estimated to be about 0.45 μmol/ml cell water. D‐Arabinono‐1,4‐lactone oxidase, which catalyses the final step in the biosynthesis of D‐erythroascorbic acid, was purified 639‐fold from the mitochondrial fraction of C. albicans to apparent homogeneity, with an overall yield of 21.2%, by a purification procedure consisting of Triton X‐100 solubilisation, ammonium sulphate precipitation, anion‐exchange, hydrophobic‐interaction, gel‐filtration and dye‐ligand chromatographies. Gel‐filtration chromatography and polyacrylamide‐gradient gel electrophoresis in the presence of deoxycholate gave apparent molecular masses of 110 kDa and 84.4 kDa, respectively. SDS/PAGE showed only one protein band corresponding to a molecular mass of 66.7 kDa. Considering the binding of detergents, the enzyme is suggested to be a single polypeptide. The enzyme showed a typical fluorescence excitation spectrum of a flavin‐containing enzyme. The flavin was not released by treatment with SDS, CCl3CO2H or boiling, indicating that it may be covalently bound to the enzyme protein. The enzyme was optimally active at 40°C and at pH 6.1. The enzyme was stable in the range pH 7.5–10. An apparent Km, value for D‐arabinono‐1,4‐lactone was 44.1 mM. L‐Galactono‐1,4‐lactone, L‐gulono‐1,4‐lactone and L‐xylono‐1,4‐lactone could also serve as substrates. Competitive inhibition was demonstrated with D‐glucono‐1,5‐lactone, L‐arabinono‐1,4‐lactone, D‐galactono‐1,4‐lactone and D‐gulono‐1,4‐lactone. P‐Chloromercuribenzoate, N ‐ethylmaleimide, iodoacetic acid, iodoacetamide and divalent metal ions such as Cd2+, Hg2+, Mn2+ and Zn2+ exhibited inhibitory effects on the enzyme.