(R)-Z-β²-HTrp(Boc)-OH | 468721-37-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (R)-Z-β²-HTrp(Boc)-OH
• 英文别名: (R)-3-{[(benzyloxy)carbonyl]amino}-2-({1-[(tert-butoxy)carbonyl]-1H-indol-3-yl}methyl)propionic acid；(2R)-2-[[1-[(2-methylpropan-2-yl)oxycarbonyl]indol-3-yl]methyl]-3-(phenylmethoxycarbonylamino)propanoic acid
• CAS: 468721-37-1
• 化学式: C₂₅H₂₈N₂O₆
• 分子量: 452.507
• InChiKey: PKVZYEDFPMOKOV-GOSISDBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  33
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  107
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (R)-Z-β²-HTrp(Boc)-OH 生成 3-[(R)-2-{(S)-5-tert-Butoxycarbonylamino-1-[((R)-2-hydroxy-propylcarbamoyl)-methyl]-pentylcarbamoyl}-3-(2-naphthalen-2-yl-acetylamino)-propyl]-indole-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  β2/β3-di- and α/β3-tetrapeptide derivatives as potent agonists at somatostatin sst4 receptors

  摘要：

  Four linear beta(2)/beta(3)-di- and alpha/beta(3)-tetrapeptides (1-4) were investigated as somatostatin sst(4) receptor agonists on recombinant human and mouse somatostatin receptors. Human somatostatin receptor subtypes 1-5 (sst(1-5)), and mouse somatostatin receptor subtypes 1,3,4 and 5, were characterised using the agonist radioligands [I-125]LTT-SRIF-28, [I-125][Tyr(10)]CST14 and [I-125]CGP 23996 in stably transfected Chinese hamster lung fibroblast (CCL39) cells. The peptides bound selectively to sst4 receptors with nanomolar affinity (pK(d)=5.4-7.8). The peptides were investigated on second messenger systems both as agonists, and as antagonists to SRIF-14-mediated effects in CCL39 cells expressing mouse sst(4) receptors, via measurement of inhibition of forskolin-stimulated adenylate cyclase activity, and stimulation of luciferase expression. The peptides showed full agonism or pronounced partial agonism (40 to 100% relative intrinsic activity) in both inhibition of forskolin-stimulated adenylate cyclase activity (pEC(50)=5.5-6.8), and luciferase expression (pEC(50)=5.5-6.5). The agonist potential was confirmed since antagonism was very difficult to establish. The data show that beta(2)/beta(3)-di- and alpha/beta(3)-tetrapeptide derivatives have agonist potential at recombinant somatostatin sst(4) receptors. Therefore, they may be used to elucidate physiological and biochemical effects mediated by sst(4), and may also have potential as therapeutic agents.

  DOI：

  10.1007/s00210-002-0673-4
• 作为产物：
  描述：

  (S)-3-[(2R)-2-({[(benzyloxy)carbonyl]amino}methyl)-3-{1-[(tert-butoxy)carbonyl]-2,3-dihydroindol-3-yl}-1-oxopropyl]-4-isopropyloxazolidin-2-one 在 lithium hydroxide 、 双氧水 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 3.5h， 生成 (R)-Z-β²-HTrp(Boc)-OH
  参考文献：
  名称：

  β-肽合成用β2-同色氨酸衍生物的制备

  摘要：

  鉴于色氨酸的 1H-indol-3-yl 侧链在肽和蛋白质中的突出作用，重要的是有适当保护的同系物 H-β2HTrpOH 和 H-β3HTrpOH（图）可用于掺入 β-肽。β2-HTrp 结构单元特别重要，因为 β2-氨基酸残基会导致 β-肽链折叠成不寻常的 12/10 螺旋或发夹弯。描述了通过琥珀酸衍生物的 Curtius 降解（方案 1）制备 Fmoc 和 Zβ2-HTrp(Boc)OH（方案 2-4）。为此，(S)-4-isopropyl-3-[(N-Boc-indol-3-yl)propionyl]-1,3-oxazolidin-2-one 烯醇化物用 BrCH2CO2Bn 烷基化（方案 3）。随后的氢解、Curtius 降解和 Evans 辅助基团的去除得到所需的 (R)-Hβ2-HTrpOH 衍生物（方案 4）。

  DOI：

  10.1002/1522-2675(200206)85:6<1567::aid-hlca1567>3.0.co;2-t