4-methoxyphenyl O-(2,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3-di-O-(4-methylbenzoyl)-β-D-xylopyranoside | 475101-60-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 4-methoxyphenyl O-(2,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3-di-O-(4-methylbenzoyl)-β-D-xylopyranoside
• 英文别名: 4-methoxyphenyl O-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3-di-O-(4-methylbenzoyl)-β-D-xylopyranoside；4-methoxyphenyl O-(2,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1-4)-2,3-di-O-(4-methylbenzoyl)-β-D-xylopyranoside；Gal2Ac4Ac6Ac(b1-4)[Bz(4-Me)(-2)][Bz(4-Me)(-3)]Xyl(b)-O-Ph(4-OMe)；[(2S,3R,4S,5R)-5-[(2S,3R,4S,5R,6R)-3,5-diacetyloxy-6-(acetyloxymethyl)-4-hydroxyoxan-2-yl]oxy-2-(4-methoxyphenoxy)-3-(4-methylbenzoyl)oxyoxan-4-yl] 4-methylbenzoate
• CAS: 475101-60-1
• 化学式: C₄₀H₄₄O₁₆
• 分子量: 780.78
• InChiKey: MXPHTMYXMZLYPY-CPXTWNBBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  56
• 可旋转键数：
  18
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  198
• 氢给体数：
  1
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  4-methoxyphenyl O-(2,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3-di-O-(4-methylbenzoyl)-β-D-xylopyranoside 在 (1,5-cyclooctadiene)(MePh₂P)2Ir*PF₆ 三氟甲磺酸三甲基硅酯 、 氢气 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.75h， 生成 4-methoxyphenyl 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-xylopyranoside
  参考文献：
  名称：

  Synthetic Approach Toward the Partial Sequences of Betaglycan in the Linkage Region on Solid Support and in Solution Phase

  摘要：

  We have synthesized, for the first time, the partial sequence of the betaglycan composed of the tetraosyl hexapeptide, which was directly usable as a probe for enzymatic glycosyl transfer. Stepwise elongation afforded the corresponding tetraosyl trichloroacetimidate. The common glycosyl dipeptide:[beta-D-GlcA-(1 -> 3)-beta-D-Gal-(1 -> 3)-beta-D-Gal-(1 -> 4)-beta-D- Xyl-(1 -> O)-Ser-Gly] was synthesized by glycosylation of the corresponding tetraosyl trichloroacetimidate and Ser-Gly moiety. The glycosyl dipeptide was coupled with other core peptide parts in solution phase and on a solid support. These glycosyl hexapeptides were then transformed into the desired target compounds.

  DOI：

  10.1080/07328300701296810
• 作为产物：
  描述：

  tetra-O-acetyl-β-D-xylopyranose 在 (1,5-cyclooctadiene)(MePh₂P)2Ir*PF₆ 吡啶 、 甲醇 、 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 camphor-10-sulfonic acid 、 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 生成 4-methoxyphenyl O-(2,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3-di-O-(4-methylbenzoyl)-β-D-xylopyranoside
  参考文献：
  名称：

  Synthetic Approach Toward the Partial Sequences of Betaglycan in the Linkage Region on Solid Support and in Solution Phase

  摘要：

  We have synthesized, for the first time, the partial sequence of the betaglycan composed of the tetraosyl hexapeptide, which was directly usable as a probe for enzymatic glycosyl transfer. Stepwise elongation afforded the corresponding tetraosyl trichloroacetimidate. The common glycosyl dipeptide:[beta-D-GlcA-(1 -> 3)-beta-D-Gal-(1 -> 3)-beta-D-Gal-(1 -> 4)-beta-D- Xyl-(1 -> O)-Ser-Gly] was synthesized by glycosylation of the corresponding tetraosyl trichloroacetimidate and Ser-Gly moiety. The glycosyl dipeptide was coupled with other core peptide parts in solution phase and on a solid support. These glycosyl hexapeptides were then transformed into the desired target compounds.

  DOI：

  10.1080/07328300701296810

文献信息

• Synthesis of betaglycan-type tetraosyl hexapeptide: a possible precursor regulating enzymatic elongation toward heparin
  作者：Jun-ichi Tamura、Akihiro Yamaguchi、Junko Tanaka

  DOI：10.1016/s0960-894x(02)00327-x

  日期：2002.8

  Tetraosyl hexapeptide, a part of the sequence of betaglycan: beta-D-GlcA-(1-->3)-beta-D-Gal-(1-->3)-beta-D-Gal-(1-->4)-beta-D-Xyl-(1-->O-SerGlyTrpProAspGly (1), which was designed as a probe for glycan elongation toward heparin, was synthesized in a stereocontrolled manner. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Synthesis of the glycosaminoglycan–protein linkage tetraosyl peptide moieties of betaglycan, which serve as a hexosamine acceptor for enzymatic glycosyl transfer
  作者：Jun-ichi Tamura、Tomomi Nakamura-Yamamoto、Yuko Nishimura、Shuji Mizumoto、Jun Takahashi、Kazuyuki Sugahara

  DOI：10.1016/j.carres.2010.06.019

  日期：2010.10

  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.