Acetylglucosamine | 24667-51-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Acetylglucosamine
• 英文别名: β-D-galactopyranosyl-(1->3)-[(α-L-fucopyranosyl)-(1->4)]-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1->3)-β-D-galactopyranosyl-(1->4)-D-glucopyranose sodium salt；β-D-Galp(1->3)-[α-L-Fucp(1->4)]-β-D-GlcpNAc(1->3)-β-D-Galp(1->4)-D-Glcp；β-D-Gal-(1->3)-[α-L-Fuc-(1->4)]-β-D-GlcNAc-(1->3)-β-D-Gal-(1->4)-D-Glc；lacto-N-fucopentaose II (LNF II)；Lewis A pentasaccharide；lacto-N-fucopentaose II；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-6-(hydroxymethyl)-4-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5-[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-3-yl]acetamide
• CAS: 24667-51-4
• 化学式: C₃₂H₅₅NO₂₅
• 分子量: 853.78
• InChiKey: DUKURNFHYQXCJG-JEOLMMCMSA-N

物化性质

• 沸点：
  1191.1±65.0 °C(Predicted)
• 密度：
  1.74±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -9.6
• 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：

  Acetylglucosamine 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：

  O-(2,3,4-tri-O-acetyl-α-L-fucopyranosyl)-(1<*>4)-O-<(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1<*>3)>-(2-acetamido-6-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1<*>3)-O-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1<*>4)-1,2,3,6-tetra-O-acetyl-α/β-D 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 48.0h， 以100%的产率得到Acetylglucosamine
  参考文献：
  名称：

  Toepfer, Alexander; Schmidt, Richard R., Journal of Carbohydrate Chemistry, 1993, vol. 12, # 7, p. 809 - 822

  摘要：

  DOI：

文献信息

• 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).
• Chemo-enzymatic supported synthesis of the 3-sulfated Lewisa pentasaccharide on a multimeric polyethylene glycol
  作者：Annie Malleron、Christine Le Narvor

  DOI：10.1016/j.carres.2008.01.005

  日期：2008.4

  The 3-sulfated Lewis(a) pentasaccharide was synthesized on multimeric-based polyethylene glycol support. Coupling of O-(2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl)-(1 -> 3)-4,6-di-O-acetyl-2-deoxy-2-phthalimido-beta-D-glucopyranosyl trichloroacetimidate with (2,6-di-O-acetyl-beta-D-galactopyranosyl)-(1 -> 4)-(2,3,6-tri-O-acetyl-beta-D-glucopyranoside) bound onto the polymer afforded lacto-N-tetraose, which was then regioselectively sulfated at the 3-OH position of the terminal galactose using the stannylene procedure. Fucosylation of the sulfated tetrasaccharide was performed using an immobilized fucosyltransferase FucTIII to give the title compound after cleavage. (C) 2008 Elsevier Ltd. All rights reserved.
• Toepfer, Alexander; Schmidt, Richard R., Journal of Carbohydrate Chemistry, 1993, vol. 12, # 7, p. 809 - 822
  作者：Toepfer, Alexander、Schmidt, Richard R.

  DOI：——

  日期：——
• High-performance liquid chromatography/electrospray ionization ion-trap mass spectrometry for analysis of oligosaccharides derivatized by reductive amination and N,N-dimethylation
  作者：Anders Broberg

  DOI：10.1016/j.carres.2007.04.020

  日期：2007.8

  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.