lacto-N-fucopentaose I | 21973-26-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: lacto-N-fucopentaose I
• 英文别名: α-L-Fucp(1->2)-β-D-Galp(1->3)-β-D-GlcpNAc(1->3)-β-D-Galp(1->4)-D-Glcp；α-L-Fuc-(1->2)-β-D-Gal-(1->3)-β-D-GlcNAc-(1->3)-β-D-Gal-(1->4)-D-Glc；lacto-neo-fucopentaose；α-L-Fuc-(1→2)-β-D-Gal-(1→3)-β-D-GlcNAc-(1→3)-β-D-Gal-(1→4)-D-Glc；Fuc(α1,2)Gal(β1,3)GlcNAc(β1,3)Gal(β1,4)Glc；Fuc(α1-2)Gal(β1-3)GlcNAc(β1-3)Gal(β1-4)Glc；Lnfp I；N-[(2S,3R,4R,5S,6R)-2-[(2R,3S,4S,5R,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-[(2R,3S,4R,5R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxyoxan-4-yl]oxy-4-[(2R,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• CAS: 21973-26-2；125276-00-8；125276-01-9
• 化学式: C₃₂H₅₅NO₂₅
• 分子量: 853.78
• InChiKey: FZIVHOUANIQOMU-YIHIYSSUSA-N

物化性质

• 沸点：
  1211.2±65.0 °C(Predicted)
• 密度：
  1.74±0.1 g/cm3(Predicted)
• 碰撞截面：
  269.6 Ų [M+Li]+ [CCS Type: DT, Method: stepped-field]

计算性质

• 辛醇/水分配系数(LogP)：
  -9
• 重原子数：
  58
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  416
• 氢给体数：
  16
• 氢受体数：
  25

反应信息

• 作为反应物：
  描述：

  lacto-N-fucopentaose I 在 sodium cyanoborohydride 作用下， 以 甲醇 、 乙醇 、 水 、 溶剂黄146 为溶剂， 反应 1.08h， 生成
  参考文献：
  名称：

  High-performance liquid chromatography/electrospray ionization ion-trap mass spectrometry for analysis of oligosaccharides derivatized by reductive amination and N,N-dimethylation

  摘要：

  Milk oligosaccharides derivatized by reductive amination with benzylamine followed by N,N-dimethylation (DMBA-oligosaccharides), were analyzed by high-performance liquid chromatography/electro spray ionization ion-trap mass spectrometry (HPLC/ESI-ITMS). Separation of DMBA-oligosaccharides was achieved on a graphitized carbon column eluted with aqueous acetonitrile and the DMBA-oligosaccharides were detected by positive-ion mode ESI-ITMS allowing sample amounts down to similar to 30 fmol of single DMBA-oligosaccharides injected on the HPLC column. MS/MS operation of the mass spectrometer resulted in the detection of diagnostic fragments, mainly belonging to the Y-series, allowing differentiation between isomeric milk oligosaccharides. HPLC/ESI-ITMS/MS/MS experiments indicated the migration of fucose residues of the DMBA milk oligosaccharides to the modified reducing end glucose residue during analysis, a migration previously only observed for proton adduct ions. (c) 2007 Published by Elsevier Ltd.

  DOI：

  10.1016/j.carres.2007.04.020
• 作为产物：
  描述：

  6-deoxy-L-galactose 、 lacto-N-tetraose 在 Pasteurella multocida inorganic pyrophosphatase 、 N-His_6-tagged Thermosynechococcus elongatus BP-1 recombinant protein 、 recombinant L-fucokinase/GDP-fucose pyrophosphorylase 、 5’-三磷酸腺苷 、 Guanosine 5'-triphosphate 、 magnesium chloride 作用下， 以 aq. buffer 为溶剂， 以95%的产率得到lacto-N-fucopentaose I
  参考文献：
  名称：

  The one-pot multienzyme (OPME) synthesis of human blood group H antigens and a human milk oligosaccharide (HMOS) with highly active Thermosynechococcus elongatus α1–2-fucosyltransferase

  摘要：

  通过使用一锅多酶（OPME）的细菌α1-2-岩藻糖基转移酶，LNFP I和人类血液H型抗原被高效地合成。

  DOI：

  10.1039/c5cc10646j

文献信息

• Congruent Strategies for Carbohydrate Sequencing. 1. Mining Structural Details by MS<i>ⁿ</i>
  作者：David Ashline、Suddham Singh、Andy Hanneman、Vernon Reinhold

  DOI：10.1021/ac050724z

  日期：2005.10.1

  Excessive fragmentation is the property of small oligomers where collisional energy within a smaller number of oscillators dissipates through extensive fragmentation. The procedures discussed in this report are unified into a singular strategy using an ion trap mass spectrometer with the sensitivity expected for electron multiplier detection. Although a small set of structures have been discussed, the

  该报告是三份系列报告中的第一份，主要针对建立一致的碳水化合物测序策略。这些报告分为（i）通过MSn分解解释小低聚物结构所有方面的分析考虑因素；（ii）使用离子片段库和相关工具进行高通量分析的数据库支持；以及（iii）用于分析的结论算法。从MSn拆卸途径定义寡糖拓扑结构。这份第一份报告的分析性贡献探索了通过离子阱质谱法暴露的结构细节的局限性，其中样品制备为甲基衍生物，并作为金属离子加合物进行了分析。这项数据挖掘工作着眼于将小寡聚物的片段与立体特异性聚糖结构相关联，结果归因于金属离子加合和分析物构象的结合。容易的糖苷裂解引入了一个不稳定性点（吡喃糖基-1-烯），该点在碰撞激活后会引发随后的环断裂。产物质量和离子强度随残基间键合，支化位置和单体立体化学而变化。过度碎片化是小型低聚物的特性，少数振荡器中的碰撞能量会通过大量碎片化消散。使用离子阱质谱仪将本报告中讨论的程序统一为单一策略，其灵敏度可预
• Characterization of<i>Helicobacter pylori</i>α1,2-Fucosyltransferase for Enzymatic Synthesis of Tumor-Associated Antigens
  作者：Daniel B. Stein、Yu-Nong Lin、Chun-Hung Lin

  DOI：10.1002/adsc.200800435

  日期：2008.10.6

  Helicobacter pylori catalyzes the fucosylation of acceptor oligosaccharides at the C2-OH of terminal Galβ units. The enzyme from strain NCTC11639 was evaluated for its ability to synthesize cancer-associated antigens. The α1,2-FucT was determined to be active over a pH range between 4.0 and 8.0 with the optimum occurring at pH 5.0. Although a divalent metal ion cofactor was not required for catalysis, enhancement

  来自幽门螺杆菌的α1,2-岩藻糖基转移酶（α1,2-FucT）催化末端Galβ单元的C2-OH上受体寡糖的岩藻糖基化。评价了来自菌株NCTC11639的酶合成癌症相关抗原的能力。经测定，α1,2-FucT在4.0至8.0的pH范围内具有活性，最适在pH 5.0时发生。尽管催化不需要二价金属离子辅助因子，但在添加Mn 2+后可检测到酶活性的增强。。详细的底物特异性分析表明，α1,2-FucT可以催化多种寡糖底物的岩藻糖基化。与包含2型结构（Galβ1-4GlcNAc）的聚糖相比，优选地，所述α1,2-FucT包含岩藻糖基化的1型结构（Galβ1-3GlcNAc）的聚糖。发现路易斯A三糖[Galβ1-3（Fucα1-4）GlcNAc]是最好的受体。唯一的例外是Lewis x五糖LNFP III [Galβ1-4（Fucα1-3）GlcNAcβ1-3Galβ1-4Glc]优于Lewis a类似物LNFP
• Detection of Oligosaccharides Labeled with Cyanine Dyes Using Matrix-Assisted Laser Desorption/Ionization Mass Spectrometry
  作者：Akihiko Kameyama、Yuko Kaneda、Hidenori Yamanaka、Hiroshi Yoshimine、Hisashi Narimatsu、Yasuro Shinohara

  DOI：10.1021/ac049897z

  日期：2004.8.1

  The sensitivity of oligosaccharides in mass spectrometry lags far behind that of peptides. This is a critical factor in realizing the high-throughput analysis of posttranslational modifications in proteomics. We here described that hydrazide derivatives of cyanine dyes (Cy3, Cy5) with a positive charge made excellent labeling reagents for the detection of oligosaccharides by matrix-assisted laser desorption/ionization mass spectrometry. Cy3-labeled standard N-glycan could be detected at 200 amol on the MALDI target plate in reflectron mode without any purification procedures after the labeling reaction, which may meet the level of sensitivity required in proteome research. Despite the general recognition that the production of signals of oligosaccharides under MALDI conditions would be highly dependent on the matrix, most of the known N-glycans from chicken ovalbumin could be detected upon Cye derivatization nearly independent of the kind of matrix tested (e.g., nor-harman, 2,5-dihydroxybenzoic acid and α-cyano-4-hydroxycinnamic acid) without spoiling the signal strength. Postsource decay afforded simple spectra mainly consisting of Y-type fragment ions, thus simplifying the sequence analysis. In-source decay afforded a similar fragmentation pattern only when acidic matrixes were used. In addition, this derivatization technique was successfully applied to the profiling of N-glycans of gel-separated glycoproteins.

  寡糖的质谱灵敏度远远落后于肽。这是实现蛋白质组翻译后修饰高通量分析的关键因素。我们在此描述了带有正电荷的花青染料（Cy3、Cy5）的酰肼衍生物是用于通过基质辅助激光解吸/电离质谱检测低聚糖的优异标记试剂。 Cy3标记的标准N-聚糖可在MALDI靶板上以反射模式检测到200 amol，标记反应后无需任何纯化步骤，可满足蛋白质组研究所需的灵敏度水平。尽管普遍认为 MALDI 条件下寡糖信号的产生高度依赖于基质，但大多数已知的来自鸡卵清蛋白的 N-聚糖可以在 Cye 衍生化时检测到，几乎独立于所测试的基质类型（例如，也不是-harman、2,5-二羟基苯甲酸和 α-氰基-4-羟基肉桂酸）而不破坏信号强度。源后衰变提供了主要由 Y 型碎片离子组成的简单光谱，从而简化了序列分析。仅当使用酸性基质时，源内衰变才提供类似的碎片模式。此外，这种衍生化技术还成功应用于凝胶分离糖蛋白的 N-聚糖分析。
• Tandem mass spectrometric analysis of fixed-charge derivatized oligosaccharides
  作者：B. Domon、D. R. Mueller、W. J. Richter

  DOI：10.1002/oms.1210291204

  日期：1994.12

  AbstractVarious derivatives of a set of three isomeric (linear and branched) pentasaccharides (LNF‐1, LNF‐2 and LNF‐3) were prepared and investigated by high‐performance tandem mass spectrometry in order to compare their collision‐induced dissociation (CID) behaviour. The fast atom bombardment tandem mass spectra of [M + H]+ ions of peracetylated derivatives mainly display fragments containing the non‐reducing terminus (B‐type ions) and allow a straightforward assignment of sugar sequence and branching together with the identification of some interglycosidic linkages. Permethylated derivatives, which better accommodate the mass range of tandem mass spectrometers in the case of larger oligosaccharides, yield similar results, i.e. predominance of B ions, but the necessary information has to be retrieved from incomplete Bi and Yi ion series. By contrast, CID of permethyl or peracetyl derivatives carrying a preformed charge due to prior reductive amination of the oligosaccharides with trimethyl(p‐aminophenyl)ammonium chloride yields exclusively fragment ions comprising the reducing end. In this case, the four distinct series of fragments observed involve charge‐remote fragmentation processes. As a consequence, the spectral patterns are not significantly affected by the nature of the sugar O‐substituents additionally introduced (i.e. methyl or acetyl).
• Novel substrate specificities of two lacto-N-biosidases towards β-linked galacto-N-biose-containing oligosaccharides of globo H, Gb5, and GA1
  作者：Aina Gotoh、Toshihiko Katoh、Yuta Sugiyama、Shin Kurihara、Yuji Honda、Haruko Sakurama、Taiho Kambe、Hisashi Ashida、Motomitsu Kitaoka、Kenji Yamamoto、Takane Katayama

  DOI：10.1016/j.carres.2015.03.005

  日期：2015.5

  We describe the novel substrate specificities of two independently evolved lacto-N-biosidases (LnbX and LnbB) towards the sugar chains of globo-and ganglio-series glycosphingolipids. LnbX, a non-classified member of the glycoside hydrolase family, isolated from Bifidobacterium longum subsp. longum, was shown to liberate galacto-N-biose (GNB: Gal beta 1-3GalNAc) and 2'-fucosyl GNB (a type-4 trisaccharide) from Gb5 pentasaccharide and globo H hexasaccharide, respectively. LnbB, a member of the glycoside hydrolase family 20 isolated from Bifidobacterium bifidum, was shown to release GNB from Gb5 and GA1 oligosaccharides. This is the first report describing enzymatic release of beta-linked GNB from natural substrates. These unique activities may play a role in modulating the microbial composition in the gut ecosystem, and may serve as new tools for elucidating the functions of sugar chains of glycosphingolipids. (C) 2015 Elsevier Ltd. All rights reserved.