p-nitrophenyl β-D-maltotrioside | 56808-39-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-nitrophenyl β-D-maltotrioside
• 英文别名: (2R,3R,4S,5S,6R)-2-(((2R,3S,4R,5R,6R)-6-(((2R,3S,4R,5R,6S)-4,5-Dihydroxy-2-(hydroxymethyl)-6-(4-nitrophenoxy)tetrahydro-2H-pyran-3-yl)oxy)-4,5-dihydroxy-2-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol；(2R,3R,4S,5S,6R)-2-[(2R,3S,4R,5R,6R)-6-[(2R,3S,4R,5R,6S)-4,5-dihydroxy-2-(hydroxymethyl)-6-(4-nitrophenoxy)oxan-3-yl]oxy-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 56808-39-0
• 化学式: C₂₄H₃₅NO₁₈
• 分子量: 625.538
• InChiKey: BETIRLUWOMCBBJ-KKFBLJMZSA-N

物化性质

• 沸点：
  971.0±65.0 °C(Predicted)
• 密度：
  1.75±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -4.7
• 重原子数：
  43
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  304
• 氢给体数：
  10
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  p-nitrophenyl β-D-maltotrioside 、 苯甲醛二甲缩醛 在 对甲苯磺酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  基于环糊精的α-淀粉酶发色底物的合成

  摘要：

  摘要一锅乙酰化和随后部分乙酰化的α-，β-和γ-环糊精分别导致结晶的过乙酰化麦芽六糖，-庚糖和-八糖。β-环糊精的长时间乙酰水解得到乙酰化的麦芽低聚糖的混合物，从中分离出过乙酰化的麦芽三糖，-四糖和-戊糖。将乙酰化的低聚糖转化为α-乙酰溴衍生物，然后转化为4-硝基苯基和2-氯-4-硝基苯基β-糖苷。由4-硝基苯基糖苷制备4，6-O-亚苄基衍生物，其与游离糖苷一起用作猪胰腺α-淀粉酶的底物。一锅乙酰化并随后部分环糊精乙酰化，导致过乙酰化的麦芽低聚体（dp 3-8），

  DOI：

  10.1016/s0008-6215(97)00187-0
• 作为产物：
  描述：

  2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl-(1->4)-2,3,6-tri-O-acetyl-α-D-glucopyranosyl-(1->4)-2,3,6-tri-O-acetyl-α-D-glucopyranosyl-bromide 在 吡啶 、 sodium methylate 、 silver carbonate 作用下， 以 甲醇 为溶剂， 反应 26.5h， 生成 p-nitrophenyl β-D-maltotrioside
  参考文献：
  名称：

  基于环糊精的α-淀粉酶发色底物的合成

  摘要：

  摘要一锅乙酰化和随后部分乙酰化的α-，β-和γ-环糊精分别导致结晶的过乙酰化麦芽六糖，-庚糖和-八糖。β-环糊精的长时间乙酰水解得到乙酰化的麦芽低聚糖的混合物，从中分离出过乙酰化的麦芽三糖，-四糖和-戊糖。将乙酰化的低聚糖转化为α-乙酰溴衍生物，然后转化为4-硝基苯基和2-氯-4-硝基苯基β-糖苷。由4-硝基苯基糖苷制备4，6-O-亚苄基衍生物，其与游离糖苷一起用作猪胰腺α-淀粉酶的底物。一锅乙酰化并随后部分环糊精乙酰化，导致过乙酰化的麦芽低聚体（dp 3-8），

  DOI：

  10.1016/s0008-6215(97)00187-0

文献信息

• Direct Synthesis of <i>para</i>-Nitrophenyl Glycosides from Reducing Sugars in Water
  作者：Xin Qiu、Antony J. Fairbanks

  DOI：10.1021/acs.orglett.0c00728

  日期：2020.3.20

  be directly converted into the corresponding para-nitrophenyl (pNP) glycosides using 2-chloro-1,3-dimethylimidazolinium chloride (DMC), para-nitrophenol, and a suitable base in aqueous solution. The reaction is stereoselective for sugars with either a hydroxyl or an acetamido group at position 2, yielding the 1,2-trans pNP glycosides. A judicious choice of base allows extension to di- and oligosaccharide

  可以使用2-氯-1,3-二甲基咪唑啉鎓氯化物（DMC），对硝基苯酚和合适的碱在水溶液中将还原糖直接转化为相应的对硝基苯基（p NP）糖苷。对于在2位具有羟基或乙酰氨基的糖，该反应是立体选择性的，产生1，2-反式p NP糖苷。碱的明智选择允许扩展至二糖和寡糖底物，包括从天然来源分离的复杂的N-聚糖低聚糖，而无需任何保护基团的操作
• SYNTHETIC CATALYSTS FOR CARBOHYDRATE PROCESSING
  申请人：Iowa State University Research Foundation, Inc.

  公开号：US20220016612A1

  公开（公告）日：2022-01-20

  The disclosure relates to molecularly-imprinted cross-linked micelles that can selectively hydrolyze carbohydrates.

  该披露涉及分子印迹交联微胶束，可以选择性地水解碳水化合物。
• Acceptor-induced modification of regioselectivity in CGTase-catalyzed glycosylations of p-nitrophenyl-glucopyranosides
  作者：Simon Strompen、Alfonso Miranda-Molina、Agustín López-Munguía、Edmundo Castillo、Gloria Saab-Rincón

  DOI：10.1016/j.carres.2014.11.010

  日期：2015.3

  transfer reactions besides showing low hydrolytic activity. Here, the effect of the anomeric configuration of the glycosyl acceptor on the regioselectivity of CGTase catalyzed glycosylations was investigated. For this purpose, the α and β anomers of p-nitrophenyl-D-glucopyranoside were used as glycosyl acceptors, Bacillus macerans and Thermoanaerobacter sp. CGTases were used as biocatalysts and β-cyclodextrin

  据报道，环糊精糖基转移酶（CGTase）除了表现出低的水解活性外，还可以选择性催化α（1→4）-糖基转移反应。在此，研究了糖基受体的异头构型对CGTase催化的糖基化区域选择性的影响。为此，将对硝基苯基-D-吡喃葡萄糖苷的α和β端基异构体用作糖基受体，Macerans芽孢杆菌和Thermoanaerobacter sp.。CGTase被用作生物催化剂，β-环糊精被用作糖基供体。如所预期的，当将对硝基苯基-α-D-吡喃葡萄糖苷与豆腐芽孢杆菌CGTase用作受体时，产生了对硝基苯基-α-D-吡喃葡萄糖基-（1→4）-O-α-D-吡喃葡萄糖苷。令人惊讶的是，当使用对硝基苯基-β-D-吡喃葡萄糖苷作为糖基受体时，除了预期的α（1→4）-糖基化产物外，还获得了α（1→3）-和α（1→6）-转移产物。还观察到嗜热厌氧菌sp.macerans CGTase区域选择性的这种意想不到的变化，导致α（1→4）
• Examination of the active sites of human salivary α-amylase (HSA)
  作者：Lili Kandra、Gyöngyi Gyémánt

  DOI：10.1016/s0008-6215(00)00221-4

  日期：2000.11

  The action pattern of human salivary amylase (HSA) was examined by utilising as model substrates 2-chloro-4-nitrophenyl (CNP) beta -glycosides of maltooligosaccharides of dp 4-8 and some 4-nitrophenyl (NP) derivatives modified at the nonreducing end with a 4,6-O-benzylidene (Bnl) group. The product pattern and cleavage frequency were investigated by product analysis using HPLC. The results revealed that the binding region in HSA is longer than five subsites usually considered in the literature and suggested the presence of at least six subsites; four glycone binding sites (- 4, - 3, - 2, - 1) and two aglycone binding sites (+ 1, + 2). In the ideal arrangement, the six subsites are filled by a glucosyl unit and the release of maltotetraose (G(4)) from the nonreducing end is dominant. The benzylidene group was also recognisable by subsites (- 3) and ( - 4). The binding modes of the benzylidene derivatives indicated a favourable interaction between the Bnl group and subsite (- 3) and an unfavourable one with subsite (- 4). Thus, subsite (- 4) must be more hydrophylic than hydrophobic. As compared with the action of porcine pancreatic alpha -amylase (PPA) on the same substrates, the results showed differences in the three-dimensional structure of active sites of HSA and PPA. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Synthesis of chromogenic substrates of α-amylases on a cyclodextrin basis
  作者：Erzsébet Farkas、Lóránt Jánossy、János Harangi、Lili Kandra、András Lipták

  DOI：10.1016/s0008-6215(97)00187-0

  日期：1997.10

  transformed into 4-nitrophenyl and 2-chloro-4-nitrophenyl β-glycosides. From the 4-nitrophenyl glycosides 4,6-O-benzylidene derivatives were prepared, which were used together with the free glycosides as substrates of porcine pancreatic α-amylase. One-pot acetylation and subsequent partial acetolysis of cyclodextrins resulted in the peracetylated maltooligomers (dp 3–8), which were transformed into 4-nitrophenyl

  摘要一锅乙酰化和随后部分乙酰化的α-，β-和γ-环糊精分别导致结晶的过乙酰化麦芽六糖，-庚糖和-八糖。β-环糊精的长时间乙酰水解得到乙酰化的麦芽低聚糖的混合物，从中分离出过乙酰化的麦芽三糖，-四糖和-戊糖。将乙酰化的低聚糖转化为α-乙酰溴衍生物，然后转化为4-硝基苯基和2-氯-4-硝基苯基β-糖苷。由4-硝基苯基糖苷制备4，6-O-亚苄基衍生物，其与游离糖苷一起用作猪胰腺α-淀粉酶的底物。一锅乙酰化并随后部分环糊精乙酰化，导致过乙酰化的麦芽低聚体（dp 3-8），