o-chloro-p-nitrophenyl β-maltotetraoside | 145072-72-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: o-chloro-p-nitrophenyl β-maltotetraoside
• CAS: 145072-72-6
• 化学式: C₃₀H₄₄ClNO₂₃
• 分子量: 822.125
• InChiKey: WOQXBWUIUQFCGE-HTLWHAQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -7.1
• 重原子数：
  55.0
• 可旋转键数：
  13.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  379.97
• 氢给体数：
  13.0
• 氢受体数：
  23.0

反应信息

• 作为反应物：
  描述：

  o-chloro-p-nitrophenyl β-maltotetraoside 在 human salivary α-amylase 、 sodium chloride 、 calcium chloride 作用下， 以 phosphate buffer 为溶剂， 生成 (2R,3R,4S,5S,6R)-2-[(2R,3S,4R,5R,6S)-6-(2-氯-4-硝基苯氧基)-4,5-二羟基-2-(羟基甲基)四氢吡喃-3-基]氧基-6-(羟基甲基)四氢吡喃-3,4,5-三醇 、 2-氯-4-硝基苯基-beta-D-葡糖-吡喃糖苷 、 2-氯-4-硝基苯基-β-D-麦芽三糖糖苷
  参考文献：
  名称：

  Examination of the active sites of human salivary α-amylase (HSA)

  摘要：

  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.

  DOI：

  10.1016/s0008-6215(00)00221-4
• 作为产物：
  描述：

  trideca-O-acetyl-α-maltotetraosyl bromide 在 吡啶 、 sodium methylate 、 silver carbonate 作用下， 以 甲醇 为溶剂， 反应 26.5h， 生成 o-chloro-p-nitrophenyl β-maltotetraoside
  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

• 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.
• Chemoenzymatic preparation of 2-chloro-4-nitrophenyl β-maltooligosaccharide glycosides using glycogen phosphorylase b
  作者：Lili Kandra、Gyöngyi Gyémánt、András Lipták

  DOI：10.1016/s0008-6215(98)00324-3

  日期：1999.1

  In the present work, we aimed to develop a new chemoenzymatic procedure for the synthesis of beta-maltooligosaccharide glycosides. The primer in the enzymatic reaction was 2-chloro-4-nitrophenyl beta-maltoheptaoside (G(7)-CNP), which was synthesised from beta-cyclodextrin (beta-CD) using a very convenient chemical method [E. Farkas, L. Janossy, J. Harangi, L. Kandra, A. Liptak, Carbohydr. Res., 303 (1997) 407-415]. Shorter chain length CNP-maltooligosaccharides in the range of dp 3-6 were prepared using rabbit skeletal muscle glycogen phosphorylase b (EC 2.4.1.1). Detailed enzymological investigations revealed that the conversion of G(7)-CNP was highly dependent on the conditions of phosphorolysis. A 100% conversion of G(7)-CNP was achieved during 10 min in 1 M phosphate buffer (pH 6.8) at 30 degrees C with the tetramer glycoside (77%) as the main product. Phosphorolysis at 10 degrees C for 10 min resulted in 89% conversion and G(4), G(5)-, and G(6)-CNP oligomers were detected in the ratio of 39:26:34%, respectively. The reaction pattern was investigated using an HPLC system. The preparative scale isolation of G(3-->6)-CNP glycosides was achieved by size-exclusion column chromatography (SEC) on Toyopearl HW-40 matrix. The productivity of the synthesis was improved by yields of up to 70-75%. (C) 1999 Elsevier Science Ltd. All rights reserved.