4-methylphenyl-2-azido-3,4-O-isopropylidene-2-deoxy-6-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-1-thio-β-D-galactopyranoside | 875484-87-0

• 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-methylphenyl-2-azido-3,4-O-isopropylidene-2-deoxy-6-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-1-thio-β-D-galactopyranoside
• CAS: 875484-87-0
• 化学式: C₃₀H₃₉N₃O₁₃S
• 分子量: 681.718
• InChiKey: NCSSJSZELWADBF-XUPQEWSSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.11
• 重原子数：
  47.0
• 可旋转键数：
  11.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  200.11
• 氢给体数：
  0.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  4-methylphenyl-2-azido-3,4-O-isopropylidene-2-deoxy-6-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-1-thio-β-D-galactopyranoside 在 4 A molecular sieve 、 溶剂黄146 、 DMTST 作用下， 以 乙醚 、 二氯甲烷 、 甲苯 为溶剂， 反应 7.0h， 生成 (2S,3R)-3-[(2S,3R,4R,5R,6R)-3-Azido-4,5-dihydroxy-6-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-pyran-2-yloxy]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-butyric acid 2-oxo-2-phenyl-ethyl ester
  参考文献：
  名称：

  Chemical synthesis of analogs of the glycopeptide contulakin-G, an analgetically active conopeptide from Conus geographus

  摘要：

  Cone snails are marine predators that use immobilizing venoms for catching prey. Chemical analysis of the venoms has revealed a variety of biologically active small and intermediate size peptides rich in post-translational modifications (modified amino acids, glycosylation). The glycopeptide contulakin-G(pGlu-Ser-Glu-Glu-Gly-Gly-Ser-Asn-Ala-[beta-D-Galp-(1 -> 3)-alpha-D-GalpNAc(I ->]Thr-Lys-Lys-Pro-Tyr-Ile-Leu-OH) is a potent analgesic from Conus geographus venom. The in vivo activity of synthetic contulakin-G was previously found to be significantly higher compared to that of a peptide lacking the glycan. In order to further investigate the importance of the glycan, we have now synthesized analogs of contulakin-G where the glycan chain O-linked to threonine has been altered either to beta-D-Galp-(1 -> 3)-P-D-GalpNAc-, alpha-D-Galp-(1 -> 3)-alpha-D-GalpNAc-, or beta-D-Galp-(1 -> 6)-alpha-D-GalP-NAc-. The glycopeptides were assembled on a Wang resin using commercially available Fmoc amino acids and synthetically prepared Fmoc-protected threonine derivatives carrying O-acetyl protected sugar chains. The final products were thoroughly characterized by NMR and mass spectroscopy. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2005.11.010
• 作为产物：
  描述：

  p-methylphenyl 2-deoxy-2-azido-1-thio-β-D-galactopyranoside 在 4 A molecular sieve 、 silver trifluoromethanesulfonate 、 对甲苯磺酸 作用下， 以 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 反应 2.0h， 生成 4-methylphenyl-2-azido-3,4-O-isopropylidene-2-deoxy-6-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-1-thio-β-D-galactopyranoside
  参考文献：
  名称：

  Chemical synthesis of analogs of the glycopeptide contulakin-G, an analgetically active conopeptide from Conus geographus

  摘要：

  Cone snails are marine predators that use immobilizing venoms for catching prey. Chemical analysis of the venoms has revealed a variety of biologically active small and intermediate size peptides rich in post-translational modifications (modified amino acids, glycosylation). The glycopeptide contulakin-G(pGlu-Ser-Glu-Glu-Gly-Gly-Ser-Asn-Ala-[beta-D-Galp-(1 -> 3)-alpha-D-GalpNAc(I ->]Thr-Lys-Lys-Pro-Tyr-Ile-Leu-OH) is a potent analgesic from Conus geographus venom. The in vivo activity of synthetic contulakin-G was previously found to be significantly higher compared to that of a peptide lacking the glycan. In order to further investigate the importance of the glycan, we have now synthesized analogs of contulakin-G where the glycan chain O-linked to threonine has been altered either to beta-D-Galp-(1 -> 3)-P-D-GalpNAc-, alpha-D-Galp-(1 -> 3)-alpha-D-GalpNAc-, or beta-D-Galp-(1 -> 6)-alpha-D-GalP-NAc-. The glycopeptides were assembled on a Wang resin using commercially available Fmoc amino acids and synthetically prepared Fmoc-protected threonine derivatives carrying O-acetyl protected sugar chains. The final products were thoroughly characterized by NMR and mass spectroscopy. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2005.11.010