4-methoxyphenyl O-[methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate]-(1->3)-O-2,4,6-tri-O-acetyl-β-D-galactopyranoside | 1254303-60-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-methoxyphenyl O-[methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate]-(1->3)-O-2,4,6-tri-O-acetyl-β-D-galactopyranoside
• 英文别名: 4-methoxyphenyl O-[methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate]-(1-3)-O-2,4,6-tri-O-acetyl-β-D-galactopyranoside
• CAS: 1254303-60-0
• 化学式: C₃₂H₄₀O₁₉
• 分子量: 728.658
• InChiKey: ILSLURYTZKFHKI-KDUCXOHCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  51.0
• 可旋转键数：
  13.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  230.25
• 氢给体数：
  0.0
• 氢受体数：
  19.0

反应信息

• 作为反应物：
  描述：

  4-methoxyphenyl O-[methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate]-(1->3)-O-2,4,6-tri-O-acetyl-β-D-galactopyranoside 在 ammonium cerium (IV) nitrate 、 水 作用下， 以 乙腈 为溶剂， 以69%的产率得到
  参考文献：
  名称：

  Synthesis of the glycosaminoglycan–protein linkage tetraosyl peptide moieties of betaglycan, which serve as a hexosamine acceptor for enzymatic glycosyl transfer

  摘要：

  Betaglycan, also known as TGF-beta type III receptor, is a membrane-anchored proteoglycan, which has two glycosaminoglycan (GAG) attachment sites (Lopez-Casillas, F.; Payne, H. M.; Andres, J. L.; Massague, J. J. Cell Biol. 1994, 124, 557-568). Chondroitin sulfate (CS) or heparan sulfate (HS) can attach to the first site, Ser(535), whereas only CS attaches to the second, Ser(546). Although the mechanism behind the assembly of CS and HS is not fully understood, it has been reported that the assembly of HS requires not only a cluster of acidic residues but also hydrophobic residues located near the Ser-Gly attachment sites (Esko, J. D. Zhang, L Curr. Opin. Struct. Biol. 1996, 6, 663-670). To further understand the effects of amino acids close to the Ser residues of the GAG-attachment sites on the glycosyltransferases, two tetraosyl peptides derived from the CS attachment sites of betaglycan, GLcA-Gal-Gal-Xyl-SerGlyAspAsnGly (1) and GLcA-Gal-Gal-Xyl-SerGlyAspAsnGlyPheProGly (2), were synthesized, and used as donor substrates for beta 1,4-N-acetylgalactosaminyltransferase-I (alpha 4GaINAcT-I) and alpha 1,4-N-acetylglucosaminyltransferase-I (beta 4GlcNAcT-I). Both the chemically synthesized linkage region tetrasaccharides were far better acceptors for beta 4GalNAcT-I than for alpha 4GlcNAcT-1 in vitro, although they also showed appreciable acceptor activity for alpha 4GlcNAcT-I. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2010.06.019
• 作为产物：
  描述：

  3,4,6-三邻乙酰基-alpha-D-吡喃葡萄糖 1,2-(原酸甲酯) 、 p-methoxyphenyl 2,4,6-tri-O-acetyl-β-D-galactopyranoside 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 0.83h， 以24%的产率得到4-methoxyphenyl O-[methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate]-(1->3)-O-2,4,6-tri-O-acetyl-β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of the glycosaminoglycan–protein linkage tetraosyl peptide moieties of betaglycan, which serve as a hexosamine acceptor for enzymatic glycosyl transfer

  摘要：

  Betaglycan, also known as TGF-beta type III receptor, is a membrane-anchored proteoglycan, which has two glycosaminoglycan (GAG) attachment sites (Lopez-Casillas, F.; Payne, H. M.; Andres, J. L.; Massague, J. J. Cell Biol. 1994, 124, 557-568). Chondroitin sulfate (CS) or heparan sulfate (HS) can attach to the first site, Ser(535), whereas only CS attaches to the second, Ser(546). Although the mechanism behind the assembly of CS and HS is not fully understood, it has been reported that the assembly of HS requires not only a cluster of acidic residues but also hydrophobic residues located near the Ser-Gly attachment sites (Esko, J. D. Zhang, L Curr. Opin. Struct. Biol. 1996, 6, 663-670). To further understand the effects of amino acids close to the Ser residues of the GAG-attachment sites on the glycosyltransferases, two tetraosyl peptides derived from the CS attachment sites of betaglycan, GLcA-Gal-Gal-Xyl-SerGlyAspAsnGly (1) and GLcA-Gal-Gal-Xyl-SerGlyAspAsnGlyPheProGly (2), were synthesized, and used as donor substrates for beta 1,4-N-acetylgalactosaminyltransferase-I (alpha 4GaINAcT-I) and alpha 1,4-N-acetylglucosaminyltransferase-I (beta 4GlcNAcT-I). Both the chemically synthesized linkage region tetrasaccharides were far better acceptors for beta 4GalNAcT-I than for alpha 4GlcNAcT-1 in vitro, although they also showed appreciable acceptor activity for alpha 4GlcNAcT-I. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2010.06.019