Z-β²-HLys(Boc)-OH | 1027602-36-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Z-β²-HLys(Boc)-OH
• 英文别名: (S)-6-{[(tert-butoxy)carbonyl]amino}-2-{[(benzyloxycarbonyl)amino]methyl}-hexanoyl acid；(S)-2-[(benzyloxycarbonylamino)methyl]-6-(tert-butoxycarbonylamino)hexanoic acid；(2S)-6-[(2-methylpropan-2-yl)oxycarbonylamino]-2-(phenylmethoxycarbonylaminomethyl)hexanoic acid
• CAS: 1027602-36-3
• 化学式: C₂₀H₃₀N₂O₆
• 分子量: 394.468
• InChiKey: HBQLIKRBEZTXQM-INIZCTEOSA-N

物化性质

• 沸点：
  599.0±50.0 °C(Predicted)
• 密度：
  1.160±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  28
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  114
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Z-β²-HLys(Boc)-OH 在 三异丙基硅烷 、 四丁基氟化铵 、 三氟乙酸 作用下， 以 水 为溶剂， 生成 (R)-3-hydroxybutyryl-(S)-β²-HLys-(S)-β³-HTrp-2-phenylethylamide
  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：

  叔丁氧羰酰基6-氨基己酸 在 lithium hydroxide monohydrate 、 叠氮磷酸二苯酯 、 palladium 10% on activated carbon 、 氢气 、 双氧水 、 三乙胺 、 lithium chloride 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 水 、 乙酸乙酯 为溶剂， -78.0~20.0 ℃ 、101.33 kPa 条件下， 反应 53.5h， 生成 Z-β²-HLys(Boc)-OH
  参考文献：
  名称：

  反式六氢苯并恶唑烷酮在含有蛋白质侧链的 β2-氨基酸的对映选择性合成中

  摘要：

  描述了使用对映体纯反式六氢苯并恶唑烷酮作为手性助剂在两种对映体形式中含有蛋白质侧链（β2-h苯丙氨酸和β2-h赖氨酸）的两种β2-氨基酸的对映选择性合成。基于 X 射线衍射分析和化学关联方法分配绝对构型。

  DOI：

  10.1002/ejoc.201301834

文献信息

• Peptide Folding Induces High and Selective Affinity of a Linear and Small β-Peptide to the Human Somatostatin Receptor 4
  作者：Karl Gademann、Thierry Kimmerlin、Daniel Hoyer、Dieter Seebach

  DOI：10.1021/jm010816q

  日期：2001.7.1

  analysis, Figure 2) and there is high and specific nanomolar affinity for hsst(4) receptor (Table 1). In contrast, the isomer 2 bearing the Lys side chain in 3-, rather than in the 2-position, has a 1000-fold smaller affinity to hsst(4). The syntheses of the required Fmoc-protected beta-amino acids (8-11, 17) are described (Schemes 1-3). Coupling of the beta-amino acids was achieved by the manual solid-phase

  已知相邻残基（具有（S）构型）的2和3位侧链的β肽会折叠并形成一个转角（类似于α肽β转角）。因此，我们合成了适当取代的β-四肽衍生物，以模拟生长激素抑制素与人类受体hsst（1-5）的结合，后者已知会在含有氨基酸残基Thr，Lys，Trp，和Phe。N-乙酰基肽酰胺Ac-beta（3）-HThr-beta（2）-HLys-beta（3）-HTrp-beta（3）-HPhe-NH（2）（1）确实显示了有针对性的拟态模拟：Lys CH（2）基团位于Trp吲哚环的屏蔽锥中（通过NMR分析，图2），并且对hsst（4）受体具有很高的纳摩尔亲和力（表1）。相比之下，带有Lys侧链的异构体2位于3-位，而不是位于2位，与hsst（4）的亲和力小1000倍。描述了所需的Fmoc保护的β-氨基酸（8-11、17）的合成（方案1-3）。β-氨基酸的偶联是通过手动固相技术在Rink树脂上完成的。
• β2/β3-di- and α/β3-tetrapeptide derivatives as potent agonists at somatostatin sst4 receptors
  作者：Caroline Nunn、Magnus Rueping、Daniel Langenegger、Edi Schuepbach、Thierry Kimmerlin、Peter Micuch、Konstanze Hurth、Dieter Seebach、Daniel Hoyer

  DOI：10.1007/s00210-002-0673-4

  日期：2003.2

  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.
• <i>trans</i>-Hexahydrobenzoxazolidinones in the Enantioselective Synthesis of β²-Amino Acids Containing Proteinogenic Side Chains
  作者：Yamir Bandala、Gloria Reyes-Rangel、Arturo Obregón-Zúñiga、Carlos Cruz-Hernández、Gerardo Corzo、Eusebio Juaristi

  DOI：10.1002/ejoc.201301834

  日期：2014.4

  The use of enantiopure trans-hexahydrobenzoxazolidinones as chiral auxiliaries in the enantioselective synthesis of two β2-amino acids containing proteinogenic side chains (β2-hPhenylalanine and β2-hLysine), in both enantiomeric forms, is described. Absolute configurations were assigned on the basis of X-ray diffraction analysis and chemical correlation methods.

  描述了使用对映体纯反式六氢苯并恶唑烷酮作为手性助剂在两种对映体形式中含有蛋白质侧链（β2-h苯丙氨酸和β2-h赖氨酸）的两种β2-氨基酸的对映选择性合成。基于 X 射线衍射分析和化学关联方法分配绝对构型。