N-乙酰基葡萄糖胺六聚寡糖1-4 | 13319-33-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: N-乙酰基葡萄糖胺六聚寡糖1-4
• 英文名称: N,N',N'',N'',N'''',N'''''-hexaacetyl chitohexaose
• 英文别名: β-hexa-N-acetylchitohexose；hexa-N-acetylchitohexaose；chitin hexamer；(GlcNAc)6；(GlcNAc)₆；AcChitosan；beta-D-GlcpNAc-(1->4)-beta-D-GlcpNAc-(1->4)-beta-D-GlcpNAc-(1->4)-beta-D-GlcpNAc-(1->4)-beta-D-GlcpNAc-(1->4)-beta-D-GlcpNAc；N-[(2R,3R,4R,5S,6R)-5-[(2S,3R,4R,5S,6R)-3-acetamido-5-[(2S,3R,4R,5S,6R)-3-acetamido-5-[(2S,3R,4R,5S,6R)-3-acetamido-5-[(2S,3R,4R,5S,6R)-3-acetamido-5-[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,4-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• CAS: 13319-33-0
• 化学式: C₄₈H₈₀N₆O₃₁
• 分子量: 1237.18
• InChiKey: GVTXKCFKWGVHBK-YZIYJOPFSA-N

物化性质

• 沸点：
  1648.3±65.0 °C(Predicted)
• 密度：
  1.62±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -13.3
• 重原子数：
  85
• 可旋转键数：
  22
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  559
• 氢给体数：
  20
• 氢受体数：
  31

反应信息

• 作为反应物：
  描述：

  N-乙酰基葡萄糖胺六聚寡糖1-4 、 氨基硫脲 在 N-甲基吗啉氧化物 作用下， 以 水 为溶剂， 反应 1.5h， 生成
  参考文献：
  名称：

  Preparation and cell culture behavior of self-assembled monolayers composed of chitohexaose and chitosan hexamer

  摘要：

  Chitohexaose and chitosan hexamer were site-selectively modified at each reducing end with thiosemicarbazide, followed by self-assembly chemisorption of the S-derivatives on a gold substrate via. S-Au bonding. Quartz crystal microbalance analysis and X-ray photoelectron spectroscopy suggested successful formation of self-assembled monolayers (SAMs) consisting of chitin and chitosan with sugar densities 0.39 and 0.35 chains nm(-2), respectively. As-prepared SAMs were very hydrophilic (with water contact angles 12-13 degrees) and flat at the nanometer scale (RMS approximate to 1.7 nm). Mouse fibroblasts (NIH-3T3) preferentially adhered to both SAMs, while fewer cells were attached to the more hydrophobic, intact gold substrate. The fixed carbohydrates induced good proliferation of NIH-3T3 cells, while surface treatment with free sugars had almost no positive effects. This architectural design of water-soluble oligosaccharide-SAMs is expected to provide a new approach for functional development of carbohydrate-decorated biointerfaces. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carbpol.2010.04.015
• 作为产物：
  描述：

  chitotriose 在 phosphate buffer 作用下， 反应 106.0h， 生成 N-乙酰基葡萄糖胺六聚寡糖1-4
  参考文献：
  名称：

  糖苷酶催化的寡糖合成：米曲霉的β - N-乙酰基己糖胺酶制备N-乙酰基壳寡糖，spenta- N-乙酰基壳五糖和六-N-乙酰基己糖

  摘要：

  使用来自米曲霉的粗β - N-乙酰基己糖胺酶，三-N-乙酰基壳三糖（GlcNAc）3（1，n = 1）和四-N-乙酰基壳四糖（GlcNAc）4（1，n = 2）分别充当两个糖基供体和糖基受体，得到含有大量相应的五糖和六糖[分别为1（n = 3）和1（n = 4）]的产物混合物，可以通过木炭-Celite色谱法轻松分离和纯化该混合物。

  DOI：

  10.1016/0957-4166(95)00370-5

文献信息

• Enzymic synthesis of useful chito-oligosaccharides utilizing transglycosylation by chitinolytic enzymes in a buffer containing ammonium sulfate
  作者：Taichi Usui、Hidenori Matsui、Kiyoshi Isobe

  DOI：10.1016/0008-6215(90)80046-6

  日期：1990.8

  aoside in a buffer medium containing ammonium sulfate, converting the tetrasaccharide into hexa-N-acetylchitohexaose (39.6%) and di-N-acetylchitobiose (55.7%) as the major products. Sugar-chain elongation from di-N-acetylchitobiose as the initial substrate to hexa-N-acetyl-chitohexaose and hepta-N-acetylchitoheptaose was also efficiently induced through lysozyme catalysis in the presence of ammonium

  从里氏木霉KDR-11的培养滤液中纯化的几丁质酶有效地催化了含有硫酸铵的缓冲液中四-N-乙酰壳聚糖四糖苷的转糖基化反应，将四糖转化为六-N-乙酰壳聚糖六糖（39.6％）和二-N-乙酰壳聚糖二糖（55.7％）为主要产品。在高浓度（30％）的硫酸铵存在下，通过溶菌酶催化，还可以有效地诱导糖基从二氮杂乙酰基壳二糖作为初始底物到六氮杂乙酰基壳六糖和七氮杂乙酰基庚庚糖的延伸。在这种情况下，向反应体系中添加硫酸铵导致六聚体和七聚体的产量显着增加，这是理想的生物活性寡糖。
• Purification and Characterization of A Novel Chitinase Isozyme from Yam Tuber
  作者：Yasuyuki ARAKANE、Daizo KOGA

  DOI：10.1271/bbb.63.1895

  日期：1999.1

  A new chitinase isozyme (Chitinase A), which had only one optimum pH toward a long substrate, glycolchitin, was purified from the peel of yam tuber by CTAB (hexadecyl trimethyl ammonium bromide) treatment and ammonium sulfate fractionation, followed by column chromatography on DEAE-Cellulofine A-500, chromatofocusing, and gel filtration on Sephacryl S-100. The molecular weight was 28,000 by SDS-PAGE. The isoelectric point was 3.6. The optimum pH was 4.0 toward both a polymer substrate, glycolchitin, and an oligosaccharide substrate, GlcNAc5. The optimum temperature was 60°C. Chitinase A was stable between pH 6 and 11 and below 45°C. Kinetic analysis was done using a series of N-acetylchitooligosaccharides (GlcNAcn, n=2 to 6) and glycolchitin as the substrates. Chitinase A hydrolyzed N-acetylchitooligosaccharides in an endo/random fashion except the disaccharide, and released the monosaccharide from all hydrolyzed oligosaccharides. This enzyme preferred oligosaccharides with the longer chain lengths. Chitinase A was inhibited 76% by 55 μM allosamidin, which is known to be a specific inhibitor of insect chitinases.

  一种新的几丁质酶同工酶（几丁质酶A）从山药块茎的果皮中纯化出来，它对长基质（乙二醇几丁质）只有一个最佳pH值，通过CTAB（十六烷基三甲基溴化铵）处理和硫酸铵分级，然后在DEAE-Cellulofine A-500上进行柱色谱、色谱聚焦和Sephacryl S-100凝胶过滤。SDS-PAGE的分子量为28,000。等电点为3.6。对聚合物基质（乙二醇几丁质）和寡糖基质（GlcNAc5）的最佳pH值均为4.0。最佳温度为60°C。几丁质酶A在pH 6至11和45°C以下稳定。使用一系列N-乙酰基几丁糖寡糖（GlcNAcn，n=2至6）和乙二醇几丁质作为底物进行动力学分析。几丁质酶A以内切/随机方式水解N-乙酰基几丁糖寡糖（二糖除外），并从所有水解的寡糖中释放出单糖。这种酶更喜欢具有较长链长的寡糖。几丁质酶A被55μM的异胍抑制76%，已知异胍是昆虫
• The behavior of chitin towards anhydrous hydrogen fluoride. Preparation of β-(1→4)-linked 2-acetamido-2-deoxy-d-glucopyranosyl oligosaccharides
  作者：Claude Bosso、Jacques Defaye、Alain Domard、Andrée Gadelle、Christian Pedersen

  DOI：10.1016/s0008-6215(00)90099-5

  日期：1986.11

  Abstract Fluorohydrolysis of chitin in anhydrous hydrogen fluoride led to β-(1→4)-linked 2-acetamido-2-deoxy- d -glucopyranosyl oligosaccharides in almost quantitative yield. The average d.p. depended on both reaction time and temperature, and was conveniently monitored by 13 C-n.m.r. spectroscopy and gel-exclusion chromatography. Preparative fractionation of oligosaccharides of chitin (d.p. 2–10)

  摘要甲壳素在无水氟化氢中的氟水解几乎可以定量获得β-（1→4）-连接的2-乙酰氨基-2-脱氧-d-吡喃葡萄糖基寡糖。平均dp取决于反应时间和温度，可以方便地通过13 Cn.mr光谱和凝胶排阻色谱法进行监测。几丁质寡糖的制备级分（dp 2-10）可通过凝胶排阻色谱法在Bio-Gel P-4中方便地实现。
• Enzymatic Synthesis of Sialyl Lactosamine Grafted Chitooligosaccharides
  作者：Jun Yan、Jianghua Li、Zhifei Hu、Xiaoyao Ma、Yun Li、Xihuan Hu、Jinfeng Ye、Wei Wang、Renzhong Wan、Hongzhi Cao

  DOI：10.1002/cjoc.202300004

  日期：——

  An efficient enzymatic assembly strategy was developed for the concise synthesis of structurally well-defined sialylated chitooligosaccharides. Two enzyme modules for the β-1,3-N-acetyl-glucosaminylation and β-1,4-galactosylation were applied for the grafting N-acetyl lactosamine (LacNAc) unit(s) onto the chitooligosaccharides. The LacNAc grafted chitooligosaccharides were further modified with α-2

  开发了一种有效的酶组装策略，用于简明合成结构明确的唾液酸化壳寡糖。β-1,3- N-乙酰基-葡糖胺化和 β-1,4-半乳糖基化的两个酶模块用于将N-乙酰乳糖胺 (LacNAc) 单元接枝到壳寡糖上。LacNAc 接枝壳寡糖通过两个酶促唾液酸化模块用 α-2,3- 或 α-2,6- 唾液酸化进一步修饰，生成总共 20 种唾液酸化壳寡糖。用合成的唾液酸化壳寡糖对流感病毒诱导的细胞病变进行的抑制研究表明，唾液酸键和链长都有助于结合偏好和抑制效力。