N-tert-butoxycarbonyl O-[2-azido-4,6-O-benzylidene-2-deoxy-3-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-α-D-galactopyranosyl]-L-threonine tert-butylester | 875484-84-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-tert-butoxycarbonyl O-[2-azido-4,6-O-benzylidene-2-deoxy-3-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-α-D-galactopyranosyl]-L-threonine tert-butylester
• CAS: 875484-84-7
• 化学式: C₆₀H₇₂N₄O₁₄
• 分子量: 1073.25
• InChiKey: IIVAPGOEOURGRT-AOGDTROPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.23
• 重原子数：
  78.0
• 可旋转键数：
  22.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  205.69
• 氢给体数：
  1.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  N-tert-butoxycarbonyl O-[2-azido-4,6-O-benzylidene-2-deoxy-3-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-α-D-galactopyranosyl]-L-threonine tert-butylester 在 palladium on activated charcoal 、 氢气 作用下， 以 乙醇 为溶剂， 反应 48.0h， 生成 (2S,3R)-3-[(2S,3R,4R,5R,6R)-3-Amino-5-hydroxy-6-hydroxymethyl-4-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-2-tert-butoxycarbonylamino-butyric acid tert-butyl 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：

  苯基2,3,4,6-四-O-苯甲基-1-硫代-Β-D-半乳糖皮蒽 在 4 A molecular sieve 、 溴 、 DMTST 作用下， 以 乙醚 、 二氯甲烷 、 甲苯 为溶剂， 反应 49.25h， 生成 N-tert-butoxycarbonyl O-[2-azido-4,6-O-benzylidene-2-deoxy-3-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-α-D-galactopyranosyl]-L-threonine tert-butylester
  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