chitotetraose

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: chitotetraose
• 英文别名: (GlcNAc)4；tetra-N-acetylchitotetraose；GlcNAc(b1-4)GlcNAc(b1-4)GlcNAc(b1-4)b-GlcNAc；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-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-2,4-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• 化学式: C₃₂H₅₄N₄O₂₁
• 分子量: 830.795
• InChiKey: PFZKWTWCVGDJQC-AOMJWMKZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -9
• 重原子数：
  57
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  383
• 氢给体数：
  14
• 氢受体数：
  21

反应信息

• 作为反应物：
  描述：

  chitotetraose 在 硫酸氢铵 、 phosphate buffer 、 acetate buffer 作用下， 反应 8.0h， 生成 N-乙酰基葡萄糖胺六聚寡糖1-4
  参考文献：
  名称：

  在含硫酸铵的缓冲液中利用几丁质分解酶的转糖基作用，对有用的壳寡糖进行酶促合成。

  摘要：

  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。

  DOI：

  10.1016/0008-6215(90)80046-6
• 作为产物：
  描述：

  在 吡啶 、 甲醇 、 sodium methylate 作用下， 生成 chitotetraose 、 N,N',N'',N'''-tetraacetyl-chitotetraose
  参考文献：
  名称：

  High-Efficiency Synthesis of Chitooligosaccharides

  摘要：

  固相合成壳寡糖的方法被描述如下：在合成NHCbz三氯乙亚胺酯供体6和14之后，使用Wang树脂作为载体进行固相合成。通过迭代的糖基化反应、催化氢化、乙酰化和脱乙酰化，分别得到了示例性的四乙酰化壳四糖1。

  DOI：

  10.2174/157017811794557877

文献信息

• Glycosidase-catalysed oligosaccharide synthesis: preparation of N-acetylchitooligosaccharides using the β-N-acetylhexosaminidase of Aspergillus oryzae
  作者：Suddham Singh、John Packwood、Christopher J. Samuel、P. Critchley、David H.G. Crout

  DOI：10.1016/0008-6215(95)00302-9

  日期：1995.12

  beta-N-acetylhexosaminidase of Jack bean (Canavalia ensiformis) or the beta-N-acetylhexosaminidase of A. oryzae, respectively. Di-N-acetylchitobiose [GlcNAc(beta 1-4)GlcNAc] is an efficient donor of 2-acetamido-2-deoxy-D-glucopyranosyl units in reactions catalysed by the N-acetylhexosaminidase of A. oryzae. Di-N-acetylchitobiose itself acts as acceptor to give tri-N-acetylchitotriose [GlcNAc(beta 1-4)GlcNAc(beta

  米曲霉的β-N-乙酰基己糖胺酶催化2-乙酰氨基-4-O-（2-乙酰氨基-2-脱氧-β-D-吡喃葡萄糖基）-2-脱氧-D-吡喃葡萄糖（二-N-乙酰基壳二糖）的形成）和对乙酰苯基2-乙酰氨基-2-脱氧β-D-吡喃葡萄糖苷中的2-乙酰氨基-6-O-（2-乙酰氨基-2-脱氧-β-D-吡喃葡萄糖基）-2-脱氧-D-吡喃葡萄糖和2-乙酰氨基-2-脱氧-D-吡喃葡萄糖。两种二糖的比例是时间依赖性的。在糖基供体消失时，（1-> 4）-与（1-> 6）异构体的比例最大（约9：1）。如果继续发展，该比率将变为（1-> 6）异构体的92：8。（1-> 4）-或（1-> 6）-异构体可以通过分别用Jack bean（Canavalia ensiformis）的β-N-乙酰基己糖苷酶或米曲霉的β-N-乙酰基己糖苷酶处理适当富集的二糖混合物来分离。在由米曲霉的N-乙酰基己糖胺酶催化的反应中，二-N-乙酰基壳二糖[Gl
• Purification, cDNA cloning, and characterization of LysM-containing plant chitinase from horsetail (<i>Equisetum arvense</i>)
  作者：Saki Inamine、Shoko Onaga、Takayuki Ohnuma、Tamo Fukamizo、Toki Taira

  DOI：10.1080/09168451.2015.1025693

  日期：2015.8.3

  Chitinase-A (EaChiA), molecular mass 36 kDa, was purified from the vegetative stems of a horsetail (Equisetum arvense) using a series of column chromatography. The N-terminal amino acid sequence of EaChiA was similar to the lysin motif (LysM). A cDNA encoding EaChiA was cloned by rapid amplification of cDNA ends and polymerase chain reaction. It consisted of 1320 nucleotides and encoded an open reading frame of 361 amino acid residues. The deduced amino acid sequence indicated that EaChiA is composed of a N-terminal LysM domain and a C-terminal plant class IIIb chitinase catalytic domain, belonging to the glycoside hydrolase family 18, linked by proline-rich regions. EaChiA has strong chitin-binding activity, however, no antifungal activity. This is the first report of a chitinase from Equisetopsida, a class of fern plants, and the second report of a LysM-containing chitinase from a plant.

  摘要：从一种铁线莲（Equisetum arvense）的营养茎中纯化出分子量为36 kDa的壳聚糖酶A（EaChiA），使用一系列柱层析技术。EaChiA的N末端氨基酸序列与赖氨酸基序（LysM）相似。通过快速扩增cDNA末端和聚合酶链反应克隆了编码EaChiA的cDNA。它由1320个核苷酸组成，编码一个361个氨基酸残基的开放阅读框。推测的氨基酸序列表明，EaChiA由一个N末端LysM结构域和一个C末端植物IIIb类壳聚糖酶催化结构域组成，属于18号糖苷水解酶家族，通过富含脯氨酸的区域连接。EaChiA具有强壳聚糖结合活性，但没有抗真菌活性。这是首次报道了来自蕨类植物Equisetopsida的壳聚糖酶，也是来自植物的第二份含有LysM的壳聚糖酶的报道。
• Synthesis of 3-<i>O</i>-β-<i>N</i>-Acetylglucosaminyl Cyclic Tetrasaccharide through a Lysozyme-catalyzed Transfer Reaction
  作者：Hikaru WATANABE、Hajime AGA、Tomohiko SONODA、Michio KUBOTA、Shigeharu FUKUDA、Masashi KURIMOTO、Yoshio TSUJISAKA

  DOI：10.1271/bbb.67.1182

  日期：2003.1

  Egg white lysozyme was found to catalyze the transfer of N-acetylglucosamine to cyclo→6)-α-D-Glcp-(1→3)-α-D-Glcp-(1→6)-α-D-Glcp-(1→3)-α-D-Glcp-(1→} (CTS). Structural analysis showed that the transfer product was3-O-β-N-acetylglucosaminyl CTS, cyclo→6)-α-D-Glcp-(1→3)-α-D-Glcp-(1→6)-[β-GlcNAc-(1→3)]-α-D-Glcp-(1→3)-α-D-Glcp-(1→}. This branched saccharide is anticipated to be a model compound of the sugar chains of glycoproteins.

  研究发现，卵清蛋白溶菌酶能够催化N-乙酰葡糖胺向环→6)-α-D-Glcp-(1→3)-α-D-Glcp-(1→6)-α-D-Glcp-(1→3)-α-D-Glcp-(1→}（CTS）的转移。结构分析显示，转移产物为3-O-β-N-乙酰葡糖胺酰CTS，环→6)-α-D-Glcp-(1→3)-α-D-Glcp-(1→6)-[β-GlcNAc-(1→3)]-α-D-Glcp-(1→3)-α-D-Glcp-(1→}。这种支链糖类有望成为糖蛋白糖链的模型化合物。
• 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。