神经节苷酯GM1(牛脑)

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 鞘脂
• 中文名称: 神经节苷酯GM1(牛脑)
• 中文别名: 神经节苷酯GM1；神经节苷脂
• 英文名称: Asialoganglioside-GM1
• 英文别名: N-[(E,2S,3R)-1-[(2R,3R,4R,5S,6R)-5-[(2S,3R,4R,5R,6R)-5-[(2S,3R,4R,5R,6R)-3-acetamido-5-hydroxy-6-(hydroxymethyl)-4-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-hydroxyoctadec-4-en-2-yl]octadecanamide
• 化学式: C₆₂H₁₁₄N₂O₂₃
• 分子量: 1255.6
• InChiKey: VELGMVLNORPMAO-HMWOVMCASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  87
• 可旋转键数：
  45
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  395
• 氢给体数：
  15
• 氢受体数：
  23

反应信息

• 作为反应物：
  描述：

  cytidine monophospho-N-acetylneuraminic acid 、 神经节苷酯GM1(牛脑) 生成 cytidine 5'-monophosphate 、 ganglioside GM1(1-) 、 氢(+1)阳离子
  参考文献：
  名称：

  Human GM3 synthase: a new mRNA variant encodes an NH2-terminal extended form of the protein

  摘要：

  All human GM(3) synthase mRNA variants until now identified predict a protein of 362 amino acids having substrate activity highly restricted to lactosylceramide. In this report we describe the identification of a new GM3 synthase transcript containing an additional translation start codon, located upstream and in-frame with that up to now considered unique translation initiation site in the human GM3 synthase gene. In vitro expression studies showed that the new transcript produces a longer form of human GM3 synthase, that is efficiently translocated into the microsomal lumen and glycosylated. Moreover, stable cDNA transfection into mammalian cells gives rise to a threefold increase of GM3 synthase activity, associated to a broader substrate specificity. Although this transcript has been initially identified in the human placenta, RT-PCR analyses verified the expression of an identical mRNA also in undifferentiated HL60 cells, but not in the monocytic lineage. Altogether, these results are the first demonstration of the existence of a new isoform of human GM3 synthase, which could play an important role during HL60 cell differentiation. The functional relevance of the existence of two isoforms of GM3 synthase is also discussed. (c) 2006 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.bbaexp.2006.07.001

文献信息

• Human GM3 synthase: a new mRNA variant encodes an NH2-terminal extended form of the protein
  作者：Patrizia Berselli、Stefania Zava、Elena Sottocornola、Simona Milani、Bruno Berra、Irma Colombo

  DOI：10.1016/j.bbaexp.2006.07.001

  日期：2006.7

  All human GM(3) synthase mRNA variants until now identified predict a protein of 362 amino acids having substrate activity highly restricted to lactosylceramide. In this report we describe the identification of a new GM3 synthase transcript containing an additional translation start codon, located upstream and in-frame with that up to now considered unique translation initiation site in the human GM3 synthase gene. In vitro expression studies showed that the new transcript produces a longer form of human GM3 synthase, that is efficiently translocated into the microsomal lumen and glycosylated. Moreover, stable cDNA transfection into mammalian cells gives rise to a threefold increase of GM3 synthase activity, associated to a broader substrate specificity. Although this transcript has been initially identified in the human placenta, RT-PCR analyses verified the expression of an identical mRNA also in undifferentiated HL60 cells, but not in the monocytic lineage. Altogether, these results are the first demonstration of the existence of a new isoform of human GM3 synthase, which could play an important role during HL60 cell differentiation. The functional relevance of the existence of two isoforms of GM3 synthase is also discussed. (c) 2006 Elsevier B.V. All rights reserved.