Gal(b1-4)GlcNAc(b1-6)[Gal(b1-3)]GalNAc(a)-O-octyl | 390400-32-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Gal(b1-4)GlcNAc(b1-6)[Gal(b1-3)]GalNAc(a)-O-octyl
• 英文别名: N-[(2R,3R,4R,5S,6R)-2-[[(2R,3R,4R,5R,6S)-5-acetamido-3-hydroxy-6-octoxy-4-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]methoxy]-4-hydroxy-6-(hydroxymethyl)-5-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-3-yl]acetamide
• CAS: 390400-32-5
• 化学式: C₃₆H₆₄N₂O₂₁
• 分子量: 860.905
• InChiKey: OOTFRRGCRSTGGF-XBFXEEPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.5
• 重原子数：
  59
• 可旋转键数：
  20
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  355
• 氢给体数：
  13
• 氢受体数：
  21

反应信息

• 作为反应物：
  描述：

  Gal(b1-4)GlcNAc(b1-6)[Gal(b1-3)]GalNAc(a)-O-octyl 在 sodium citrate buffer 、 β-galactosidase 作用下， 反应 24.0h， 以5 mg的产率得到N-[(2S,3R,4R,5R,6R)-6-((2R,3R,4R,5S,6R)-3-Acetylamino-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxymethyl)-5-hydroxy-2-octyloxy-4-((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-acetamide
  参考文献：
  名称：

  Efficient synthesis of lactosaminylated core-2 O-glycans

  摘要：

  A series of lactosaminylated oligosaccharides found in mucin type O-glycans was synthesized using a generalized block strategy. The synthesis involved the addition of a protected lactosamine donor to a partially protected T-disaccharide derivative. The nonreducing galactose residues of the deblocked oligosaccharide products could be removed by beta -galactosidase from jack bean to produce the corresponding GlcNAc terminated compounds. A series of tri- to hexasaccharides was thus efficiently produced. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00550-9
• 作为产物：
  描述：

  在 palladium dihydroxide 氢气 作用下， 生成 Gal(b1-4)GlcNAc(b1-6)[Gal(b1-3)]GalNAc(a)-O-octyl
  参考文献：
  名称：

  Efficient synthesis of lactosaminylated core-2 O-glycans

  摘要：

  A series of lactosaminylated oligosaccharides found in mucin type O-glycans was synthesized using a generalized block strategy. The synthesis involved the addition of a protected lactosamine donor to a partially protected T-disaccharide derivative. The nonreducing galactose residues of the deblocked oligosaccharide products could be removed by beta -galactosidase from jack bean to produce the corresponding GlcNAc terminated compounds. A series of tri- to hexasaccharides was thus efficiently produced. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00550-9

文献信息

• Chemoenzymatic synthesis of sialylated oligosaccharides for their evaluation in a polysialyltransferase assay
  作者：Prabal Sengupta、Anup Kumar Misra、Misa Suzuki、Minoru Fukuda、Ole Hindsgaul

  DOI：10.1016/s0040-4039(03)01509-0

  日期：2003.8

  A series of sialylated β-d-Gal-(1→3)-α-d-GalNAc-octyl containing oligosaccharides representative of those found on mucin type complex O-glycans were synthesized by a chemoenzymatic approach for use in the kinetic characterization of recently cloned polysialyltransferases. Enzymatic incorporation of N-acetylneuraminic acid (sialic acid) into the synthetic acceptors was accomplished by 2,3-(N) and (

  通过化学酶法合成了一系列唾液酸化的β-d-Gal-（1→3）-α-d-GalNAc-辛基含寡糖，代表在粘蛋白型复合O-聚糖上发现的寡糖，用于近期的动力学表征克隆的聚唾液酸转移酶。的酶促掺入Ñ -acetylneuraminic氨酸（唾液酸）到合成受体是由2,3-（完成Ñ）和（ø）-sialyltransferases，得到目标化合物6 - 10在实际的产率。