N-(9-fluorenylmethoxycarbonyl)-[O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-(1-3)-O-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1-3)-O-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1-4)-2,3-di-O-(4-methylbenzoyl)-β-D-xylopyranosyl]-L-serylglycine | 1254303-65-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-(9-fluorenylmethoxycarbonyl)-[O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-(1-3)-O-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1-3)-O-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1-4)-2,3-di-O-(4-methylbenzoyl)-β-D-xylopyranosyl]-L-serylglycine
• 英文别名: N-(9-fluorenylmethoxycarbonyl)-O-[(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-(1->3)-O-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->3)-O-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3-di-O-(4-methylbenzoyl)-β-D-xylopyranosyl]-L-serylglycine
• CAS: 1254303-65-5
• 化学式: C₇₈H₈₈N₂O₃₇
• 分子量: 1645.55
• InChiKey: IVCQZNYNHAQKJE-PYHCIOLESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.69
• 重原子数：
  117.0
• 可旋转键数：
  31.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  494.17
• 氢给体数：
  3.0
• 氢受体数：
  36.0

反应信息

• 作为反应物：
  描述：

  O-(tert-butyl)-L-aspartyl-L-asparaginylglycine methyl ester 、 N-(9-fluorenylmethoxycarbonyl)-[O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-(1-3)-O-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1-3)-O-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1-4)-2,3-di-O-(4-methylbenzoyl)-β-D-xylopyranosyl]-L-serylglycine 在 1-羟基苯并三唑 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以60.5 mg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：

  N-(9-fluorenylmethoxycarbonyl)-[O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-(1-3)-O-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1-3)-O-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1-4)-2,3-di-O-(4-methylbenzoyl)-β-D-xylopyranosyl]-L-serylglycine allyl ester 在 四(三苯基膦)钯 、 N-甲基苯胺 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以93%的产率得到N-(9-fluorenylmethoxycarbonyl)-[O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-(1-3)-O-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1-3)-O-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1-4)-2,3-di-O-(4-methylbenzoyl)-β-D-xylopyranosyl]-L-serylglycine
  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