N-(9-fluorenylmethyloxycarbonyl)-O-[2-acetamido-3,4-di-O-acetyl-2-deoxy-6-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-galactopyranosyl]-L-threonine phenacylester | 875484-89-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-(9-fluorenylmethyloxycarbonyl)-O-[2-acetamido-3,4-di-O-acetyl-2-deoxy-6-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-galactopyranosyl]-L-threonine phenacylester
• CAS: 875484-89-2
• 化学式: C₅₃H₆₀N₂O₂₂
• 分子量: 1077.06
• InChiKey: LNXFNBWBAIFGLI-QDHAIGGTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.92
• 重原子数：
  77.0
• 可旋转键数：
  21.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  305.52
• 氢给体数：
  2.0
• 氢受体数：
  22.0

反应信息

• 作为反应物：
  描述：

  N-(9-fluorenylmethyloxycarbonyl)-O-[2-acetamido-3,4-di-O-acetyl-2-deoxy-6-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-galactopyranosyl]-L-threonine phenacylester 在 锌 作用下， 以 水 、 溶剂黄146 为溶剂， 反应 2.0h， 以89%的产率得到N-(9-fluorenylmethyloxycarbonyl)-O-[2-acetamido-3,4-di-O-acetyl-2-deoxy-6-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-galactopyranosyl]-L-threonine
  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：

  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 吡啶 、 乙醚 、 二氯甲烷 、 甲苯 为溶剂， 反应 55.0h， 生成 N-(9-fluorenylmethyloxycarbonyl)-O-[2-acetamido-3,4-di-O-acetyl-2-deoxy-6-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-galactopyranosyl]-L-threonine phenacylester
  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