α-(carbobenzyloxy)nitroarginyl-ε-(carbobenzyloxy)lysylaspartic acid β-benzyl ester | 72210-37-8

• 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: α-(carbobenzyloxy)nitroarginyl-ε-(carbobenzyloxy)lysylaspartic acid β-benzyl ester
• 英文别名: Z-Arg(NO2^G)-Lys(Z)-Asp(Bzl)-OH；Z-Arg(NO2)-Lys(Z)-Asp(OBzl)-OH；Cbz-Arg(NO2)(NO2)-Lys(Cbz)(Cbz)-Asp(OBn)(OBn)-OH；(2S)-2-[[(2S)-2-[[(2S)-5-[[amino(nitramido)methylidene]amino]-2-(phenylmethoxycarbonylamino)pentanoyl]amino]-6-(phenylmethoxycarbonylamino)hexanoyl]amino]-4-oxo-4-phenylmethoxybutanoic acid
• CAS: 72210-37-8
• 化学式: C₃₉H₄₈N₈O₁₂
• 分子量: 820.857
• InChiKey: BFBSQXVXZGSJDB-CPCREDONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  59
• 可旋转键数：
  27
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  295
• 氢给体数：
  7
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  α-(carbobenzyloxy)nitroarginyl-ε-(carbobenzyloxy)lysylaspartic acid β-benzyl ester 在 N-甲基吗啉 作用下， 反应 12.05h， 生成 thymopentin
  参考文献：
  名称：

  Becu, Fr.; Becu, Chr.; Anteunis, M. J. O., Bulletin des Societes Chimiques Belges, 1991, vol. 100, # 1, p. 15 - 23

  摘要：

  DOI：
• 作为产物：
  描述：

  Boc-Lys(Z)-OCOOEt 在 N-甲基吗啉 、 TFA-anisole 、 氯甲酸乙酯 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 12.0h， 生成 α-(carbobenzyloxy)nitroarginyl-ε-(carbobenzyloxy)lysylaspartic acid β-benzyl ester
  参考文献：
  名称：

  Effects of synthetic thymopoietin II Fragments on E-rosette forming cells of a rheumatoid arthritis patient.

  摘要：

  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。

  DOI：

  10.1248/cpb.29.2322

文献信息

• Stabilized Analogs of Thymopentin. 1. 4,5-Ketomethylene Pseudopeptides
  作者：Joseph I. DeGraw、Ronald G. Almquist、Charles K. Hiebert、William T. Colwell、Jac Crase、Takeshi Hayano、Amrit K. Judd、Linda Dousman、R. Lane Smith、William R. Waud、Itsuo Uchida

  DOI：10.1021/jm950803a

  日期：1997.7.1

  The pentapeptide, thymopentin (Arg(1)-Lys(2)-Asp(3)-Val(4)-Tyr(5)) is known for its activity as an immunomodulating drug, but with limited half-life in plasma. In this first paper of a series of three studies, the synthesis of analogs stabilized at the peptide bond between the C-terminal amino acids via insertion of a ketomethylene moiety is described. N-Blocked pseudopeptides containing Val(k)Phe, Ala(k)Phe, and Val(k)Val units were prepared and attached to chloromethyl Merrifield resin via the carboxy terminal. Removal of the N-BOC group by trifluoroacetic acid was followed by sequential coupling with N-BOC dipeptides of aspartic acid to yield resin-bound N-BOC pseudotetrapeptides. Removal of N-BOC and coupling with N-BOC-r-N-tosylarginine followed by total cleavage of blocking groups and resin by HF afforded the target pseudopentapeptides. The analogs were found to compete favorably with thymopentin for binding to CEM cells, but binding was reduced by about 20-30% on average. All analogs showed significant enhancement of half-life versus thymopentin in mouse serum, but most showed only modest improvement in human serum. Insertion of proline or norleucine at position 2 in the chain caused a substantial increase in half-life (3-4-fold), while N-methylnorleucine conferred complete stability in the analogs.
• BECU, FR.;BECU, CHR.;ANTEUNIS, M. J. O., BULL. SOC. CHIM. BELG. , 100,(1991) N, C. 15-23
  作者：BECU, FR.、BECU, CHR.、ANTEUNIS, M. J. O.

  DOI：——

  日期：——