Boc-Phe-Gly-NH-CH2C6H5 | 100571-96-8

• 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: Boc-Phe-Gly-NH-CH2C6H5
• 英文别名: Boc-L-Phe-Gly-NHBn；tert-butyl N-[(2S)-1-[[2-(benzylamino)-2-oxoethyl]amino]-1-oxo-3-phenylpropan-2-yl]carbamate
• CAS: 100571-96-8
• 化学式: C₂₃H₂₉N₃O₄
• 分子量: 411.501
• InChiKey: WORYBFIJICRNEW-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  30
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  96.5
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Boc-Phe-Gly-NH-CH2C6H5 、 三氟乙酸 在 水 、 苯甲醚 作用下， 反应 0.67h， 生成 (S)-2-Amino-N-(benzylcarbamoyl-methyl)-3-phenyl-propionamide; compound with trifluoro-acetic acid
  参考文献：
  名称：

  Synthesis and opioid activity of dermorphin tetrapeptides bearing D-methionine S-oxide at position 2

  摘要：

  Eight new dermorphin tetrapeptides, X-Tyr-D-MetO-Phe-aa-Y (X = H, H2N = C(NH); aa = Gly, 2-aminoethanol, sarcosine; Y = NH2, NH-alkyl), were prepared and tested for opioid activity. They show dose-related naloxone-reversible opioid effects in vitro and in vivo. H-Tyr-D-MetO-Phe-Gly-NH2 (I) (guinea pig ileum IC50 = 13.6 nM; tail-flick ED50 = 1.97 pmol/mouse, icv, and 0.65 mumol/kg, sc), though less effective in the periphery, has central activities higher than those of dermorphin H-Tyr-D-Ala-Phe-Gly-Tyr-Pro-Ser-NH2. Following intracerebroventricular or subcutaneous administrations in mice, I is about respectively 1500 and 17 times as potent an analgesic as morphine.

  DOI：

  10.1021/jm00156a003
• 作为产物：
  描述：

  Boc-Phe-Gly-OBzl 在 palladium on activated charcoal 氢气 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 30.0h， 生成 Boc-Phe-Gly-NH-CH2C6H5
  参考文献：
  名称：

  Synthesis and opioid activity of dermorphin tetrapeptides bearing D-methionine S-oxide at position 2

  摘要：

  Eight new dermorphin tetrapeptides, X-Tyr-D-MetO-Phe-aa-Y (X = H, H2N = C(NH); aa = Gly, 2-aminoethanol, sarcosine; Y = NH2, NH-alkyl), were prepared and tested for opioid activity. They show dose-related naloxone-reversible opioid effects in vitro and in vivo. H-Tyr-D-MetO-Phe-Gly-NH2 (I) (guinea pig ileum IC50 = 13.6 nM; tail-flick ED50 = 1.97 pmol/mouse, icv, and 0.65 mumol/kg, sc), though less effective in the periphery, has central activities higher than those of dermorphin H-Tyr-D-Ala-Phe-Gly-Tyr-Pro-Ser-NH2. Following intracerebroventricular or subcutaneous administrations in mice, I is about respectively 1500 and 17 times as potent an analgesic as morphine.

  DOI：

  10.1021/jm00156a003

文献信息

• An Alkanesulfonamide “Safety-Catch” Linker for Solid-Phase Synthesis
  作者：Bradley J. Backes、Jonathan A. Ellman

  DOI：10.1021/jo981990y

  日期：1999.4.1

  An alkanesulfonamide "safety-catch" linker has been developed for tethering carboxylic acids to support. Acylation of the sulfonamide support provides a support-bound N-acylsulfonamide that is stable to both basic and strongly nucleophilic reaction conditions. At the end of a solid-phase synthesis sequence, treatment with iodoacetonitrile provides N-cyanomethyl derivatives that can be cleaved by nucleophiles under mild reaction conditions to release the target compounds. Coupling conditions have been developed to load Boc- and Fmoc-amino acids to the alkanesulfonamide resin with high loading efficiencies and minimal racemization. A number of support-bound amino acids incorporating diverse side-chain functionality have been subjected to a short synthesis sequence, followed by iodoacetonitrile activation and nucleophilic displacement to provide dipeptide products. All 20 of the proteinogenic amino acids, when suitably protected, are compatible with the loading and activation steps. Finally, displacement with various nucleophiles including amines, a-amino acid methyl esters, and a-amino acid coumarin derivatives is demonstrated.
• Synthesis and opioid activity of dermorphin tetrapeptides bearing D-methionine S-oxide at position 2
  作者：Severo Salvadori、Mauro Marastoni、Gianfranco Balboni、Gian Pietro Sarto、Roberto Tomatis

  DOI：10.1021/jm00156a003

  日期：1986.6

  Eight new dermorphin tetrapeptides, X-Tyr-D-MetO-Phe-aa-Y (X = H, H2N = C(NH); aa = Gly, 2-aminoethanol, sarcosine; Y = NH2, NH-alkyl), were prepared and tested for opioid activity. They show dose-related naloxone-reversible opioid effects in vitro and in vivo. H-Tyr-D-MetO-Phe-Gly-NH2 (I) (guinea pig ileum IC50 = 13.6 nM; tail-flick ED50 = 1.97 pmol/mouse, icv, and 0.65 mumol/kg, sc), though less effective in the periphery, has central activities higher than those of dermorphin H-Tyr-D-Ala-Phe-Gly-Tyr-Pro-Ser-NH2. Following intracerebroventricular or subcutaneous administrations in mice, I is about respectively 1500 and 17 times as potent an analgesic as morphine.