叔丁氧羰基-(苄基)苏氨酰-琥珀酰亚胺 | 32886-43-4

• 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
• 中文名称: 叔丁氧羰基-(苄基)苏氨酰-琥珀酰亚胺
• 中文别名: BOC-O-苄基-N-二环己亚胺
• 英文名称: BOC-O-benzyl-L-threonine N-hydroxysuccinimide ester
• 英文别名: N-tBoc-O-benzyl-L-threonine N-hydroxysuccinimide ester；N-Boc-O-Bzl-L-threonine N-hydroxysuccinimide ester；Boc-L-Thr(Bzl)-ONSu；Boc-Thr(O-Bzl)-OSu；Boc-Thr(Bzl)-OSu；(2,5-dioxopyrrolidin-1-yl) (2S,3R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylmethoxybutanoate
• CAS: 32886-43-4
• 化学式: C₂₀H₂₆N₂O₇
• mdl: MFCD00037905
• 分子量: 406.436
• InChiKey: SNEHQGZSMYSVFT-DYVFJYSZSA-N

物化性质

• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  111
• 氢给体数：
  1
• 氢受体数：
  7

安全信息

• WGK Germany：
  3
• 储存条件：
  -20°C

反应信息

• 作为反应物：
  描述：

  叔丁氧羰基-(苄基)苏氨酰-琥珀酰亚胺 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 1,4-二氧六环 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 Boc-L-Thr(Bzl)-L-Ala-L-Hmb-L-Amp-ONSu
  参考文献：
  名称：

  Cyclic Peptides. XXII. Synthesis of [2-Amino-2,3-dehydrobutanoic Acid⁴]AM-Toxin I

  摘要：

  为了研究2,3-脱氢丙氨酸（ΔAla）残基侧链在环状十四肽植物毒素AM-toxin I中第4位对苹果叶片坏死活性所起的作用，我们采用两种不同的方法合成了[2-氨基-2,3-脱氢丁酸4] AM-toxin I。该类似物没有毒性，表明ΔAla残基侧链在失去活性的情况下无法处理。

  DOI：

  10.1246/bcsj.59.2041
• 作为产物：
  描述：

  N-羟基丁二酰亚胺 、 N-Boc-O-苄基-L-苏氨酸 在 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 生成 叔丁氧羰基-(苄基)苏氨酰-琥珀酰亚胺
  参考文献：
  名称：

  Conformational Changes Associated with Post-Translational Modifications of Pro¹⁴³ in Skp1 of Dictyostelium—A Dipeptide Model System

  摘要：

  Prolyl hydroxylation and subsequent glycosylation of the E3(SCF) ubiquitin ligase subunit Skp1 affects its conformation and its interaction with F-box proteins and, ultimately, O-2-sensing in the organism. Taking a reductionist approach to understand the molecular basis for these effects, a series of end-capped Thr-Pro dipeptides was synthesized, tracking the sequential post-translational modifications that occur in the protein. The conformation of the pyrrolidine ring in each compound was gauged via coupling constants ((3)J(H alpha,H beta)) and the electronegativity of the C gamma-substituents by chemical shifts (C-13). The equilibrium between the cis-trans conformations about the central prolyl peptide bond was investigated by integration of signals corresponding to the two species in the H-1 NMR spectra over a range of temperatures. These studies revealed an increasing preference for the trans-conformation in the order Pro < Hyp < [alpha-(1,4)GlcNAc]Hyp. Rates for the forward and reverse reactions, determined by magnetization transfer experiments, demonstrated a reduced rate for the trans-to-cis conversion and a significant increase in the cis-to-trans conversion upon hydroxylation of the proline residue in the dipeptide. NOE experiments suggest that the Thr side chain pushes the sugar away from the pyrrolidine ring. These effects, which depended on the presence of the N-terminal Thr residue, offer a mechanism to explain altered properties of the corresponding full-length proteins.

  DOI：

  10.1021/ja5033277

文献信息

• Aminoacyl−Anthraquinone Conjugates as Telomerase Inhibitors: Synthesis, Biophysical and Biological Evaluation
  作者：Giuseppe Zagotto、Claudia Sissi、Lorena Lucatello、Claudia Pivetta、Sergio A. Cadamuro、Keith R. Fox、Stephen Neidle、Manlio Palumbo

  DOI：10.1021/jm800160v

  日期：2008.9.25

  anticancer target. To inhibit enzyme activity by induction of G-quadruplex in human telomeres, we have synthesized a small library of 2,6- and 2,7-amino-acyl/ peptidyl anthraquinones with diverse connecting linkers, charge, lipophilicity and bulk. The test compounds modulated G-quadruplex stability to different extents and showed clear preference for quadruplex over duplex DNA. Telomerase inhibition correlated

  端粒酶-端粒复合物是潜在的抗癌靶标。为了通过在人端粒中诱导G-四链体来抑制酶的活性，我们合成了一个2,6-和2,7-氨基-酰基/肽基蒽醌的小文库，具有不同的连接接头，电荷，亲脂性和体积。测试化合物在不同程度上调节了G-四链体的稳定性，并且显示出对四链体的明显偏好高于双链体DNA。端粒酶抑制与G四联体稳定相关。SAR分析表明，连接子和蒽醌之间的连接类型，以及侧链的位置和氨基酸成分的性质在稳定G-四链体和产生端粒酶抑制作用中均起着重要作用。短期细胞毒活性差。然而，长时间暴露于有效的G-四链体结合剂后，细胞会衰老。这些结果有助于合理设计更有效的G-四链体稳定剂，可能具有癌细胞选择性的抗增殖作用。
• Synthesis of human thymopoietin(hTP) and examination of its immunological effect on the impaired blastogenic response of T-lymphocytes of uremic patients.
  作者：TAKASHI ABIKO、HIROSHI SEKINO

  DOI：10.1248/cpb.36.2506

  日期：——

  The octatetracontapeptide corresponding to the entire amino acid seuence of human thymopoietin (hTP) was synthesized by assembling ten peptide fragments in solution followed by deprotection with 1 M trifluoromethanesulfonic acid-thioanisole (molar ratio, 1 : 1) in trifluoroacetic acid in the presence of dimethylselenide and m-cresol. Finally, the deprotected peptide was incubated with dithiothreitol to reduce sulfoxide on the methionine side chain. The synthetic peptide was found to have a restoring effect on the impaired blastogenic response of T-lymphocytes isolated from uremic patients.

  对应于人胸腺生成素（hTP）全部氨基酸序列的八四肽是通过在溶液中组装十个肽片段，随后使用三氟甲磺酸-噻吩（摩尔比1:1）在三氟乙酸中并加入二甲基硒和间甲酚进行脱保护，最终将脱保护的肽与二硫苏糖醇孵育以还原蛋氨酸侧链上的亚砜来合成的。研究发现，合成肽对从尿毒症患者中分离的T淋巴细胞的受损增殖反应具有恢复作用。
• Artificial ribonucleases 6. Ribonuclease activity of tetrapeptides based on amino acids involved in the catalytic site of RNase T1
  作者：L. S. Koroleva、A. A. Donina、N. V. Tamkovich、N. A. Kovalev、M. A. Zenkova、V. N. Sil’nikov

  DOI：10.1007/s11172-006-0176-4

  日期：2005.11

  Tetrapeptides based on amino acids involved in the catalytic site of RNase T1 were synthesized. These peptides interact with a 96-mer fragment of HIV-1 RNA, which results in phosphodiester bonds splitting. The efficacy of RNA cleavage depends on the mutual arrangement of oppositely charged amino acids (Glu and Arg or Lys) in a peptide. The introduction of an additional cationic fragment (based on bis-quaternary salts of 1,4-diazabicyclooctane) into an RNase mimetic leads to a considerable increase in the efficiency of RNA depolymerization.

  基于RNase T1催化位点氨基酸的四肽已被合成。这些肽与HIV-1 RNA的96-mer片段相互作用，导致磷酸二酯键断裂。RNA切割的效力取决于相反电荷氨基酸（Glu和Arg或Lys）在肽中的相互排列。将附加的阳离子片段（基于1,4-二氮杂双环[4.2.0]辛烷的双季铵盐）引入模拟RNase的结构中，显著提高了RNA解聚的效率。
• Synthesis of a thymosin .BETA.4-like peptide, deacetyl-thymosin .BETA.4Xen, and its restorative effect on depressed lymphocyte blastogenic response to phytohemagglutinin(PHA) in uremic patients.
  作者：Takashi ABIKO、Hiroshi SEKINO

  DOI：10.1248/cpb.37.2467

  日期：——

  An analog of thymosin βXen4 isolated from ooxytes of Xenopus laevis, deacetyl-thymosin βXen4, was synthesized by assembling 6 peptide fragments, followed by deprotection with 1 M trifluoromethanesulfonic acid-thioanisole (molar ratio, 1 : 1) in trifluoroacetic acid in the presence of dimethylselenium. Finally, the deprotected peptide was incubated with dithiothreitol to reduce sulfoxide on the methionine side chain. The synthetic tritetracontapeptide was found to have a restoring effect on the impaired blastogenic response of T-lymphocytes isolated from uremic patients.

  将 6 个肽段组装起来，然后在二甲基硒存在下，用 1 M 三氟甲磺酸-硫代苯甲醚（摩尔比为 1:1）在三氟乙酸中进行脱保护，从而合成了从爪蟾卵巢中分离出来的胸腺肽 βXen4 类似物--脱乙酰胸腺肽 βXen4。最后，将脱保护的肽与二硫苏糖醇孵育，以还原蛋氨酸侧链上的亚砜。研究发现，合成的三四联肽对从尿毒症患者体内分离出来的 T 淋巴细胞受损的造血反应有恢复作用。
• Design and Synthesis of Optically Active Esters of γ-Amino-β-oxo Acids as Precursors for the Synthesis of Tetramic Acids Derived from L-Serine, L-Tyrosine, and L-Threonine
  作者：Dimitris Matiadis、Olga Igglessi-Markopoulou

  DOI：10.1002/ejoc.201000700

  日期：2010.11

  Tetramic acids bearing a hydroxyalkyl or hydroxybenzyl group at C-5 of the heterocyclic ring were successfully prepared. α-Amino acids appropriately protected and activated were used as acylating agents for the C-acylation of active methylene compounds. These novel synthesized intermediates, substituted γ-amino acids, were isolated in excellent yields and enantiomeric purities. Cyclization under basic

  成功制备了杂环C-5处带有羟基烷基或羟基苄基的四羧酸。α-氨基酸被适当保护和活化用作活性亚甲基化合物的 C-酰化的酰化剂。这些新的合成中间体，取代的 γ-氨基酸，以优异的产率和对映体纯度分离。在碱性条件下环化以高产率和对映体纯度提供所需产物。