methyl 4-O-acetyl-β-D-xylopyranoside | 80973-75-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 4-O-acetyl-β-D-xylopyranoside
• 英文别名: 4-O-Ac-MeXylp；[(3R,4R,5R,6R)-4,5-dihydroxy-6-methoxyoxan-3-yl] acetate
• CAS: 80973-75-7
• 化学式: C₈H₁₄O₆
• 分子量: 206.196
• InChiKey: JHEDUCYPVRMBHQ-ULAWRXDQSA-N

物化性质

• 沸点：
  310.8±42.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  85.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N,O-双三甲硅基乙酰胺 、 methyl 4-O-acetyl-β-D-xylopyranoside 以 吡啶 为溶剂， 反应 0.25h， 生成 Acetic acid (3R,4S,5R,6R)-6-methoxy-4,5-bis-trimethylsilanyloxy-tetrahydro-pyran-3-yl ester
  参考文献：
  名称：

  Schraml, Jan; Petrakova, Eva; Pihar, Otomar, Collection of Czechoslovak Chemical Communications, 1983, vol. 48, # 7, p. 1829 - 1841

  摘要：

  DOI：
• 作为产物：
  描述：

  methyl 4‐O‐acetyl‐2,3‐O‐isopropylidene‐β‐D‐xylopyranoside 在 溶剂黄146 作用下， 以 水 为溶剂， 以80%的产率得到methyl 4-O-acetyl-β-D-xylopyranoside
  参考文献：
  名称：

  通过实验和计算方法研究吡喃糖苷中的酰基迁移。

  摘要：

  酰基迁移影响所有含有游离羟基的酰化有机化合物，特别是碳水化合物的合成、分离、操作和纯化。虽然已经报道了一些关于不同缓冲液中迁移现象的孤立研究，但缺乏对类似条件下不同单糖整体迁移过程的全面了解。在这里，我们结合实验、动力学和理论工具，使用五种不同的酰基研究了不同单糖中的酰基迁移。结果表明，单糖中的异头构型与其他羟基的相对构型和迁移酰基的性质一起对迁移速率有重大影响。全机械模型，基于计算，

  DOI：

  10.1002/chem.202200499

文献信息

• Positional specificity of Flavobacterium johnsoniae acetylxylan esterase and acetyl group migration on xylan main chain
  作者：Vladimír Puchart、Morten Gjermansen、Mária Mastihubová、Kristian B.R. Mørkeberg Krogh、Peter Biely

  DOI：10.1016/j.carbpol.2019.115783

  日期：2020.3

  are attacked with a significantly reduced affinity. The resulting 2-O-acetylated xylan was used to investigate for the first time the migration of the 2-O-acetyl group to position 3 within the polysaccharide. In contrast to easy acetyl group migration along the monomeric xylopyranosides or non-reducing-end terminal Xylp residues of xylooligosaccharides, such a migration in the polymer required much longer

  一种新的约翰逊弗氏菌分离物编码的酶与最近发现的新型乙酰木聚糖酯酶基本相同，该酶能够从4-O-甲基-d-葡萄糖醛酸取代的吡喃吡喃糖基（Xylp）残基中释放3-O-乙酰基（Razeq等等人，2018年）。除了乙酰葡糖醛酸木聚糖中2-O-MeGlcA取代的Xylp残基的去酯化作用外，该酶还对双乙酰化的Xylp残基同样起作用，从中仅释放3-O-乙酰基，而2-O-乙酰基则保持不变。3-O-单乙酰基化的木糖残基以显着降低的亲和力被攻击。所得的2-O-乙酰化木聚糖首次用于研究2-O-乙酰基向多糖内第3位的迁移。与容易的乙酰基沿着木糖寡糖的单体木糖吡喃糖苷或非还原末端Xylp残基迁移相比，这种在聚合物中的迁移需要在100°C下加热更长的时间。然而，木聚糖3-O-脱乙酰基酶的特异性对乙酰化的甲基和4-硝基苯基木吡喃葡萄糖苷没有那么严格的要求。
• Regioselective Monoacetylation of Methyl Pyranosides of Pentoses and 6‐Deoxyhexoses by Acetic Anhydride in the Presence of MoCl₅
  作者：Evgeny V. Evtushenko

  DOI：10.1080/00397910600591565

  日期：2006.6.1

  Abstract Convenient regioselective syntheses of 3‐acetates of methyl pyranosides of α‐L‐rhamnose, α‐ and β‐L‐arabinose, α‐D‐fucose, α‐D‐lyxose, and β‐D‐ribose with good yields have been attained using MoCl5 as catalyst. Methyl β‐L‐rhamnopyranoside under this conditions gave 2‐acetate.

  摘要 α-L-鼠李糖、α-和β-L-阿拉伯糖、α-D-岩藻糖、α-D-来苏糖和β-D-核糖的甲基吡喃糖苷的3-乙酸酯的方便区域选择性合成已获得良好的产率。以 MoCl5 为催化剂。在此条件下甲基β-L-吡喃鼠李糖苷生成2-乙酸酯。
• Trichoderma reesei CE16 acetyl esterase and its role in enzymatic degradation of acetylated hemicellulose
  作者：Peter Biely、Mária Cziszárová、Jane W. Agger、Xin-Liang Li、Vladimír Puchart、Mária Vršanská、Vincent G.H. Eijsink、Bjorge Westereng

  DOI：10.1016/j.bbagen.2013.10.008

  日期：2014.1

  non-reducing end sugar may involve migration of acetyl groups to position 4, which also serves as substrate of the TrCE16 esterase. CONCLUSION Concerted action of CtGH10 xylanase, an AcXE and TrCE16 AcE resulted in close to complete deacetylation of neutral xylooligosaccharides, whereas substitution with MeGlcA prevents removal of acetyl groups from only a small fraction of the aldouronic acids. Experiments

  背景技术里氏木霉CE16乙酰酯酶（AcE）是真菌的植物细胞壁降解系统的组分。该酶的作用就像是一种外向性脱乙酰基酶，可从非还原性末端糖残基上除去乙酰基。方法在这项工作中，我们证明了使用MALDI ToF MS对天然乙酰化低聚木糖的这种外脱乙酰活性。结果GH10木聚糖酶和乙酰木聚糖酯酶（AcXEs）的共同作用导致形成中性和酸性的木寡糖，主要在其非还原端带有一些抗性乙酰基。我们在这里显示这些乙酰基充当Tr​​CE16 AcE的目标。最突出的靶标是线性中性木糖寡糖的非还原性末端Xylp残基上或非还原性末端带有MeGlcA的醛糖醛酸上的3-O-乙酰基。非还原性末端糖的脱乙酰化可能涉及乙酰基向位置4的迁移，该位置4也用作TrCE16酯酶的底物。结论CtGH10木聚糖酶，AcXE和TrCE16 AcE的协同作用导致中性低聚木糖几乎完全脱乙酰，而用MeGlcA取代可防止仅从一小部分醛糖醛酸中除去乙酰基。用
• Bashir, Nazir B.; Phythian, Sara J.; Reason, Andrew J., Journal of the Chemical Society. Perkin transactions I, 1995, # 18, p. 2203 - 2222
  作者：Bashir, Nazir B.、Phythian, Sara J.、Reason, Andrew J.、Roberts, Stanley M.

  DOI：——

  日期：——
• Positional specifity of acetylxylan esterases on natural polysaccharide: An NMR study
  作者：Iveta Uhliariková、Mária Vršanská、Barry V. McCleary、Peter Biely

  DOI：10.1016/j.bbagen.2013.01.011

  日期：2013.6

  Background: Microbial degradation of acetylated plant hemicelluloses involves besides enzymes cleaving the glycosidic linkages also deacetylating enzymes. A detailed knowledge of the mode of action of these enzymes is important in view of the development of efficient bioconversion of plant materials that did not undergo alkaline pretreatment leading to hydrolysis of ester linkages.Methods: In this work deacetylation of hardwood acetylglucuronoxylan by acetybcylan esterases from Streptomyces lividans (carbohydrate esterase family 4) and Oipinomyces sp. (carbohydrate esterase family 6) was monitored by H-1-NMR spectroscopy.Results: The H-1-NMR resonances of all acetyl groups in the polysaccharide were fully assigned. The targets of both enzymes are 2- and 3-monoacetylated xylopyranosyl residues and, in the case of the Orpinomyces sp. enzyme, also the 2,3-di-O-acetylated xylopyranosyl residues. Both enzymes do not recognize as a substrate the 3-O-acetyl group on xylopyranosyl residues alpha-1,2-substituted with 4-O-methyl-D-glucuronic acid.Conclusions: The H-1-NMR spectroscopy approach to study positional and substrate specificity of AcXEs outlined in this work appears to be a simple way to characterize catalytic properties of enzymes belonging to various CE families. Significance: The results contribute to development of efficient and environmentally friendly procedures for enzymatic degradation of plant biomass. (c) 2013 Elsevier B.V. All rights reserved.