(L)-Trt-Val-OH | 47522-06-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: (L)-Trt-Val-OH
• 英文别名: Tr-Val-OH；Trt-Val-OH；N-trityl-L-valine；N-Trityl-L-valin；(2S)-3-methyl-2-(tritylazaniumyl)butanoate
• CAS: 47522-06-5
• 化学式: C₂₄H₂₅NO₂
• 分子量: 359.468
• InChiKey: RULPGAAHRDHJOK-QFIPXVFZSA-N

物化性质

• 熔点：
  157-158 °C
• 沸点：
  502.9±38.0 °C(Predicted)
• 密度：
  1.125±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (L)-Trt-Val-OH 在 magnesium 、 1,2-二溴乙烷 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 乙酸乙酯 、 乙腈 为溶剂， 反应 22.0h， 生成 7-methyl-6-[(tert-butyloxycarbonyl)amino]-3-isopropyl-1-octen-5-one
  参考文献：
  名称：

  Stabilized Analogs of Thymopentin. 1. 4,5-Ketomethylene Pseudopeptides

  摘要：

  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.

  DOI：

  10.1021/jm950803a
• 作为产物：
  描述：

  L-缬氨酸 在 甲醇 、 三乙胺 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 (L)-Trt-Val-OH
  参考文献：
  名称：

  Efficient Synthesis ofN-Triphenylmethyl α-Amino Acids

  摘要：

  已开发出一种通过其三苯甲基酯2合成N-三苯甲基（trityl）α-氨基酸3的新型一锅合成方法。

  DOI：

  10.1055/s-1989-27195

文献信息

• A Stereocontrolled Synthesis of Monofluoro Ketomethylene Dipeptide Isosteres
  作者：Robert V. Hoffman、Junhua Tao

  DOI：10.1021/jo981334y

  日期：1999.1.1

  A simple, stereocontrolled synthesis of monofluoro ketomethylene dipeptide isosteres has been developed. N-Tritylated ketomethylene dipeptide isosteres, prepared from N-tritylated amino acids, are converted to their Z-TMS enol ethers and fluorinated with Selectfluor. There is cooperative stereocontrol between the N-tritylamine group and the alkyl group at C-2. The method is short (six steps), diastereoselective

  已经开发了简单的立体控制的单氟酮亚甲基二肽等排体的合成。由N-三苯甲基化的氨基酸制备的N-三苯甲基化的酮亚甲基二肽等位基因被转化为其Z-TMS烯醇醚并用Selectfluor进行氟化。N-三苯甲基胺基和C-2处的烷基之间存在协同立体控制。该方法很短（六个步骤），非对映选择性（85-> 95％）和对映选择性（> 95％）。
• Synthesis of a Protected Heptapeptide Related to the Histidine Analogue of Hypertensin II
  作者：DIMITRIOS THEODOROPOULOS

  DOI：10.1038/1841634a0

  日期：1959.11

  HYPERTENSIN II or isoleucine hypertensin II, a pressor peptide with the amino-acid sequence Asp.Arg.Val.Tyr.Is.His.Pro.Phe. has been synthesized along classical lines by two groups of investigators1.

  高血压素II或异亮氨酸高血压素II是一种具有氨基酸序列Asp.Arg.Val.Tyr.Is.His.Pro.Phe的升压肽，已被两个研究组按照经典方法合成。
• Efficient Synthesis of<i>N</i>-Triphenylmethyl α-Amino Acids
  作者：Manfred Mutter、René Hersperger

  DOI：10.1055/s-1989-27195

  日期：——

  A new one-pot synthesis of N-triphenylmethyl(trityl) α-amino acids 3 via their trityl ester 2 has been developed.

  已开发出一种通过其三苯甲基酯2合成N-三苯甲基（trityl）α-氨基酸3的新型一锅合成方法。
• Prodrugs
  申请人：MEDIVIR AB

  公开号：US20030186924A1

  公开（公告）日：2003-10-02

  A method for treatment of HBV and HIV infections comprising administering the compound or salt of formula Ig 1

  一种治疗HBV和HIV感染的方法，包括给予化合物或公式Ig1的盐。
• Antiviral methods employing double esters of 2', 3'-dideoxy-3'-fluoroguanosine
  申请人：Zhou Xiao-Xiong

  公开号：US20060122383A1

  公开（公告）日：2006-06-08

  A method for treatment of HBV and HIV infections comprising administering the compound or salt of formula Ig

  一种治疗HBV和HIV感染的方法，包括给予化合物或公式Ig的盐。