不饱和的软骨素二寡糖 4-S 钠 | 51449-07-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 不饱和的软骨素二寡糖 4-S 钠
• 中文别名: 不饱和的软骨素二寡糖4-S钠
• 英文名称: ΔUA(1->3)GalNAc4(SO4)
• 英文别名: Chondroitin disaccharide deltadi-4S；(2R,3R,4S)-2-[(2R,3R,4S,5R)-2-acetamido-5,6-dihydroxy-1-oxo-4-sulfooxyhexan-3-yl]oxy-3,4-dihydroxy-3,4-dihydro-2H-pyran-6-carboxylic acid
• CAS: 51449-07-1
• 化学式: C₁₄H₂₁NO₁₄S
• 分子量: 459.385
• InChiKey: KRLLUAKFPATIPF-PGVXRSKGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.5
• 重原子数：
  30
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  255
• 氢给体数：
  7
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  5-甲基-2-苯基-1,2-二氢吡唑-3-酮 、 不饱和的软骨素二寡糖 4-S 钠 生成
  参考文献：
  名称：

  Determination of urinary oligosaccharides by high-performance liquid chromatography/electrospray ionization–tandem mass spectrometry: Application to Hunter syndrome

  摘要：

  The reaction of heparan sulfate (HS) and dermatan sulfate (DS) oligosaccharides with 1-phenyl-3-methyl-5-pyrazolone (PMP) yields hydrophobic derivatives that are amenable to separation by reversed-phase high-performance liquid chromatography (RP-HPLC) and analysis by electrospray ionization-tandem mass spectrometry (ESI-MS/MS). We describe here the development of an RP-HPLC-ESI-MS/MS assay for the measurement of di- to pentasaccharides derived from HS and DS in the urine of mucopolysaccharidosis (MPS) type II patients, as PMP derivatives. HPLC separation was performed on a 3-mu m Alltima C18-LL column (50 x 2.1 mm) using a gradient elution of up to 25% acetonitrile over 17 min, and an API-4000 mass spectrometer equipped with a turbo-ion-spray source was used in the negative ion multiple reaction monitoring mode for PMP-oligosaccharide determination. Using this method, we found that the derivatization kinetics of the oligosaccharides was influenced by the type of residue present at the reducing end (i.e., N-acetylglucosamine, N-acetylgalactosamine, or uronic acid). The elevation of each of the measured oligosaccharides in MPS II urine enabled complete discrimination of a cohort of MPS II patient urines from unaffected controls. This assay is rapid and reproducible and may be useful for the diagnosis of MPS II, and also for monitoring of disease progression and efficacy of therapy. (C) 2010 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.ab.2010.04.002

文献信息

• Determination of urinary oligosaccharides by high-performance liquid chromatography/electrospray ionization–tandem mass spectrometry: Application to Hunter syndrome
  作者：Timothy C. Nielsen、Tomas Rozek、John J. Hopwood、Maria Fuller

  DOI：10.1016/j.ab.2010.04.002

  日期：2010.7

  The reaction of heparan sulfate (HS) and dermatan sulfate (DS) oligosaccharides with 1-phenyl-3-methyl-5-pyrazolone (PMP) yields hydrophobic derivatives that are amenable to separation by reversed-phase high-performance liquid chromatography (RP-HPLC) and analysis by electrospray ionization-tandem mass spectrometry (ESI-MS/MS). We describe here the development of an RP-HPLC-ESI-MS/MS assay for the measurement of di- to pentasaccharides derived from HS and DS in the urine of mucopolysaccharidosis (MPS) type II patients, as PMP derivatives. HPLC separation was performed on a 3-mu m Alltima C18-LL column (50 x 2.1 mm) using a gradient elution of up to 25% acetonitrile over 17 min, and an API-4000 mass spectrometer equipped with a turbo-ion-spray source was used in the negative ion multiple reaction monitoring mode for PMP-oligosaccharide determination. Using this method, we found that the derivatization kinetics of the oligosaccharides was influenced by the type of residue present at the reducing end (i.e., N-acetylglucosamine, N-acetylgalactosamine, or uronic acid). The elevation of each of the measured oligosaccharides in MPS II urine enabled complete discrimination of a cohort of MPS II patient urines from unaffected controls. This assay is rapid and reproducible and may be useful for the diagnosis of MPS II, and also for monitoring of disease progression and efficacy of therapy. (C) 2010 Elsevier Inc. All rights reserved.