4-nitrophenyl 4-O-acetyl-β-D-xylopyranoside | 709663-88-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-nitrophenyl 4-O-acetyl-β-D-xylopyranoside
• 英文别名: 4-Nitrophenyl 4-O-acetyl-beta-D-xylopyranoside；[(3R,4R,5R,6S)-4,5-dihydroxy-6-(4-nitrophenoxy)oxan-3-yl] acetate
• CAS: 709663-88-7
• 化学式: C₁₃H₁₅NO₈
• 分子量: 313.264
• InChiKey: HMKLHLCYQSXSAH-XQHKEYJVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  131
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  4-nitrophenyl 4-O-acetyl-β-D-xylopyranoside 在 Aspergillus niger β-xylosidase 、 recombinant Cellvibrio japonicus acetyl esterase B 作用下， 以 二甲基亚砜 为溶剂， 生成 对硝基苯酚
  参考文献：
  名称：

  家族 2 的碳水化合物酯酶是 6-O-脱乙酰酶

  摘要：

  测试了来自腐生细菌 Cellvibrio japonicus 和热纤梭菌（碳水化合物酯酶 (CE) 家族 2 的成员）的三种乙酰酯酶 (AcE) 对一系列模型底物的活性，包括部分乙酰化的葡萄糖苷、甘露糖苷和吡喃木糖苷。所有三种酶都表现出对己醛糖 6 位脱乙酰化的强烈偏好。这种区域选择性不同于典型的乙酰木聚糖酯酶 (AcXE)。在醋酸乙烯饱和的水性介质中，CE-2 酶催化乙酰基转移到相同的位置，即到单糖和二糖的伯羟基。木糖和低聚木糖不作为乙酰基受体，因此 CE-2 酶似乎是 6-O-脱乙酰酶。

  DOI：

  10.1016/j.febslet.2009.11.095
• 作为产物：
  描述：

  4-nitrophenyl 2-O-acetyl-β-D-xylopyranoside 在 LPS-30 作用下， 以 phosphate buffer 、 二甲基亚砜 为溶剂， 生成 4-nitrophenyl 4-O-acetyl-β-D-xylopyranoside 、 4-nitrophenyl 3-O-acetyl-β-D-xylopyranoside
  参考文献：
  名称：

  Lipase-catalysed preparation of acetates of 4-nitrophenyl β-d-xylopyranoside and their use in kinetic studies of acetyl migration

  摘要：

  Di-O-acetates and mono-O-acetates of 4-nitrophenyl beta-D-xylopyranoside were prepared by use of lipase PS-30. Polarity of organic solvents and reaction time affected the regioselectivity of the di-O-acetylation as well as the yields of monoacetates. The kinetics of acetyl groups migration in these derivatives was studied in aqueous media using HPLC. Migration of the acetyl group strongly depended on pH. The highest rate of acetyl migration was observed from O-2 to O-3 in both 2,4-di-O-acetate and 2-O-acetate. On the contrary, acetyl exchange between O-3 and O-4 in both directions was slower than between O-2 and O-3. The 2,3-di-O-acetate and 4-O-acetate showed to be the most stable towards acetyl migration. The 3,4-di-O-acetate and 4-O-acetate were dominant in the corresponding equilibration mixtures. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2004.02.016

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。
• 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.