4-硝基苯基-alpha-D-麦芽糖苷 | 66068-37-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 4-硝基苯基-alpha-D-麦芽糖苷
• 英文名称: 4-nitrophenyl α-maltotetraoside
• 英文别名: p-nitrophenyl α-maltotetraoside；4-Nitrophenyl a-D-maltotetraoside；(2R,3R,4S,5S,6R)-2-[(2R,3S,4R,5R,6R)-6-[(2R,3S,4R,5R,6R)-6-[(2R,3S,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-(4-nitrophenoxy)oxan-3-yl]oxy-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 66068-37-9
• 化学式: C₃₀H₄₅NO₂₃
• 分子量: 787.68
• InChiKey: NPSLEEASXYBLOE-RVXWVMNCSA-N

物化性质

• 沸点：
  1123.2±65.0 °C(Predicted)
• 密度：
  1.79±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -6.9
• 重原子数：
  54
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  383
• 氢给体数：
  13
• 氢受体数：
  23

反应信息

• 作为反应物：
  描述：

  4-硝基苯基-alpha-D-麦芽糖苷 在 human salivary alpha-amylase 作用下， 以 various solvent(s) 为溶剂， 以29%的产率得到对硝基苯-α-D-葡萄糖吡喃苷
  参考文献：
  名称：

  Modified malto-oligosaccharides as inhibitors of human alpha-amylases

  摘要：

  DOI：

  10.1016/0008-6215(90)80118-m
• 作为产物：
  描述：

  maltotetraose 、 对硝基苯-α-D-葡萄糖吡喃苷 在 acetate buffer 作用下， 以 二甲基亚砜 为溶剂， 反应 4.0h， 生成 4-硝基苯基-alpha-D-麦芽糖苷 、 p-nitrophenyl 3¹-O-maltotriosyl-α-D-glucopyranoside
  参考文献：
  名称：

  Transglycosylation reaction of maltotriose-forming amylase from Streptomyces griseus

  摘要：

  A maltotriose-forming amylase from Streptomyces griseus produced predominantly p-nitrophenyl alpha-maltotetraoside through a transglycosylation reaction from maltotetraose as a donor and p-nitrophenyl alpha-D-glucopyranoside as an acceptor in an organic co-solvent. With p-nitrophenyl beta-D-glucopyranoside acceptor, the enzyme catalyzed the formation of an alpha-(1 drop 3)-linked tetrasaccharide (p-nitrophenyl 3(1)-O-alpha-maltotriosyl-beta-D-glucopyranoside in a yield of 16%, based on the acceptor added with its isomer p-nitrophenyl beta-maltotetraoside. This was also the case for the formation of o-chloro-p-nitrophenyl 3(1)-O-alpha-maltotriosyl-beta-D-glucopyranoside with o-chloro-p-nitrophenyl beta-D-glucopyranoside acceptor. The results shows that the anomeric configuration of the aryl group in the glucosyl accepters had an effect on the position of transglycosylation.

  DOI：

  10.1016/0008-6215(93)84154-x

文献信息

• 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）
• The action of germinated barley alpha-amylases on linear maltodextrins
  作者：Alex.W. MacGregor、Joan E. Morgan、E.Ann MacGregor

  DOI：10.1016/0008-6215(92)85080-j

  日期：1992.4

  The actions of barley alpha-amylase isozymes 1 and 2 (EC 3.2.1.1) on malto-oligosaccharides and their p-nitrophenyl glycosides were similar, but not identical. For each isozyme, transglycosylation occurred with small substrates that were hydrolysed with difficulty, whereas the rates of hydrolysis increased with increase in the size of the substrate for both the malto-oligosaccharides and the p-nitrophenyl glycosides. A p-nitrophenyl group was found to mimic a glucose residue to a large extent. The differences in action of the isozymes are believed to be caused by differences at more than one subsite of the active site. A lysine-arginine substitution is postulated to account for some of the observed variations.
• Ono, Mitsunori; Suzuki, Nobuo; Hirano, Shigeo, Chemistry Letters, 1991, # 3, p. 395 - 398
  作者：Ono, Mitsunori、Suzuki, Nobuo、Hirano, Shigeo、Itoh, Isamu、Masuta, Nobuhito

  DOI：——

  日期：——
• Transglycosylation reaction of maltotriose-forming amylase from Streptomyces griseus
  作者：Taichi Usui、Takeomi Murata、Yoshihiko Yabuuchi、Koichi Ogawa

  DOI：10.1016/0008-6215(93)84154-x

  日期：1993.12

  A maltotriose-forming amylase from Streptomyces griseus produced predominantly p-nitrophenyl alpha-maltotetraoside through a transglycosylation reaction from maltotetraose as a donor and p-nitrophenyl alpha-D-glucopyranoside as an acceptor in an organic co-solvent. With p-nitrophenyl beta-D-glucopyranoside acceptor, the enzyme catalyzed the formation of an alpha-(1 drop 3)-linked tetrasaccharide (p-nitrophenyl 3(1)-O-alpha-maltotriosyl-beta-D-glucopyranoside in a yield of 16%, based on the acceptor added with its isomer p-nitrophenyl beta-maltotetraoside. This was also the case for the formation of o-chloro-p-nitrophenyl 3(1)-O-alpha-maltotriosyl-beta-D-glucopyranoside with o-chloro-p-nitrophenyl beta-D-glucopyranoside acceptor. The results shows that the anomeric configuration of the aryl group in the glucosyl accepters had an effect on the position of transglycosylation.
• Modified malto-oligosaccharides as inhibitors of human alpha-amylases
  作者：Kaoru Omichi、Sumihiro Hase、Tokuji Ikenaka

  DOI：10.1016/0008-6215(90)80118-m

  日期：1990.12