N^α-tert-butyl-oxycarbonyl-N^ε-benzyloxycarbonyl-L-lysyl-N^G-nitro-L-arginine benzyl ester | 59658-49-0

• 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: N^α-tert-butyl-oxycarbonyl-N^ε-benzyloxycarbonyl-L-lysyl-N^G-nitro-L-arginine benzyl ester
• 英文别名: benzyl ester of N^α-t-butyloxycarbonyl-N^ε-benzykoxycarbonyl-L-lysyl-N^G-nitro-L-arginine；Boc-Lys(Z)-Arg(NO2)-OBzl；benzyl (2S)-5-[[amino(nitramido)methylidene]amino]-2-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-6-(phenylmethoxycarbonylamino)hexanoyl]amino]pentanoate
• CAS: 59658-49-0
• 化学式: C₃₂H₄₅N₇O₉
• 分子量: 671.751
• InChiKey: XTPLXFDGGIPSCI-UIOOFZCWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.29
• 重原子数：
  48.0
• 可旋转键数：
  18.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  223.11
• 氢给体数：
  6.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  N^α-tert-butyl-oxycarbonyl-N^ε-benzyloxycarbonyl-L-lysyl-N^G-nitro-L-arginine benzyl ester 在 钯 氢气 、 三氟乙酸 作用下， 以 甲醇 、 氯仿 、 水 、 溶剂黄146 、 乙酸乙酯 为溶剂， 反应 2.08h， 生成 N-tert-butyloxycarbonyl-L-threonyl-L-lysyl-L-arginine
  参考文献：
  名称：

  Shvachkin, Yu. P.; Tikhonov, Yu. N.; Babichev, V. N., Journal of General Chemistry of the USSR, 1985, vol. 55, # 1, p. 178 - 181

  摘要：

  DOI：
• 作为产物：
  描述：

  N-Boc-N'-Cbz-L-赖氨酸 在 N-乙基吗啉 作用下， 以 氯仿 为溶剂， 反应 1.17h， 生成 N^α-tert-butyl-oxycarbonyl-N^ε-benzyloxycarbonyl-L-lysyl-N^G-nitro-L-arginine benzyl ester
  参考文献：
  名称：

  Nawrocka, Eleonora; Siemion, Ignacy Z.; Herman, Zbigniew S., Polish Journal of Chemistry, 1988, vol. 62, # 1-3, p. 263 - 268

  摘要：

  DOI：

文献信息

• Synthesis of the octadecapeptide corresponding to positions 32 to 49 of the revised amino acid sequence of thymopoietin II and its effect on low E-rosette forming cells of an aged patient with chronic renal failure.
  作者：TAKASHI ABIKO、HIROSHI SEKINO

  DOI：10.1248/cpb.30.3271

  日期：——

  The octadecapeptide, H-Arg-Lys-Asp-Val-Tyr-Val-Glu-Leu-Tyr-Leu-Gln-Ser-Leu-Thr-Ala-Leu-Lys-Arg-OH, corresponding to positions 32 to 49 of the revised amino acid sequence of bovine thymopoietin II was synthesized by the azide condensation of three fragments, (32-36), (37-41) and (42-49), followed by deprotection with hydrogen fluoride in the presence of anisole-thioanisole-o-cresol. The in vitro addition of the synthetic thymopoietin II (32-49) significantly restored the low E-rosette forming capacity of cells from an aged patient with chronic renal failure to normal levels. The in vitro effect of [Gln38, Thr43, Val47]-thymopoietin II (32-49) on the low E-rosette forming capacity of cells from the aged patient with chronic renal failure was also compared with that of the synthetic thymopoietin II (32-49). The [Gln38, Thr43, Val47]-thymopoietin II (32-49) was approximately equipotent with the synthetic thymopoietin II (32-49) at a concentration of 100 μg/ml.

  十八肽H-Arg-Lys-Asp-Val-Tyr-Val-Glu-Leu-Tyr-Leu-Gln-Ser-Leu-Thr-Ala-Leu-Lys-Arg-OH，对应于牛胸腺生成素II修订后的氨基酸序列的第32至49位，通过三个片段(32-36)、(37-41)和(42-49)的叠氮化物缩合合成，随后在茴香硫醚-邻甲酚存在下用氢氟酸脱保护。体外添加合成的胸腺生成素II(32-49)显著恢复了来自慢性肾衰竭老年患者的细胞的低E玫瑰花形成能力至正常水平。[Gln38, Thr43, Val47]胸腺生成素II(32-49)对来自慢性肾衰竭老年患者的细胞的低E玫瑰花形成能力的影响也与合成的胸腺生成素II(32-49)进行了比较。在100 μg/ml的浓度下，[Gln38, Thr43, Val47]胸腺生成素II(32-49)与合成的胸腺生成素II(32-49)大致等效。
• Effects of synthetic thymopoietin II Fragments on E-rosette forming cells of a rheumatoid arthritis patient.
  作者：TAKASHI ABIKO、IKUKO ONODERA、HIROSHI SEKINO

  DOI：10.1248/cpb.29.2322

  日期：——

  An octadecapeptide, H-Arg-Lys-Asp-Val-Tyr-Val-Gln-Leu-Tyr-Leu-Gln-Thr-Leu-Thr-Ala-Val-Lys-Arg-OH, corresponding to the C-terminal portion of thymopoietin II was synthesized using protecting groups removable by hydrogen fluoride treatment. The in vitro addition of the synthetic octadecapeptide was able to restore the low E-rosette forming capacity of cells in a rheumatoid arthritis patient to normal levels. The in vitro effects of pentapeptide (positions 32-36), nonapeptide (positions 33-41) and decapeptide (positions 32-41) fragments of thymopoietin on the low E-rosette forming capacity of cells of a rheumatoid arthritis patient were also compared with that of the synthetic octadecapeptide. The relative potency of the pentapeptide was 10.56 and that of the decapeptide was 25.43 based on the octadecapeptide (100.00) as a standard, but the nonapeptide was ineffective.

  一种十八肽，H-Arg-Lys-Asp-Val-Tyr-Val-Gln-Leu-Tyr-Leu-Gln-Thr-Leu-Thr-Ala-Val-Lys-Arg-OH，对应于胸腺生成素II的C端部分，通过使用氢氟酸处理可去除的保护基团进行合成。体外添加这种合成的十八肽能够将类风湿关节炎患者细胞的低E玫瑰花结形成能力恢复到正常水平。还比较了胸腺生成素的三肽（位置32-36）、九肽（位置33-41）和十肽（位置32-41）片段对类风湿关节炎患者低E玫瑰花结形成细胞的体外效应与合成十八肽的效应。基于十八肽（100.00）作为标准，三肽的相对效力为10.56，十肽为25.43，但九肽无效。
• NAWROCKA, ELEONORA;SIEMION, IGNACY Z.;HERMAN, ZBIGNIEW S.;LASKAWIEC, GRZE+, POL. J. CHEM., 62,(1988) N-3, C. 263-268
  作者：NAWROCKA, ELEONORA、SIEMION, IGNACY Z.、HERMAN, ZBIGNIEW S.、LASKAWIEC, GRZE+

  DOI：——

  日期：——
• Synthesis of miniluliberin
  作者：Yu. P. Shvachkin、Yu. N. Tikhonov

  DOI：10.1007/bf00575203

  日期：1983.11