Boc-S-苄基-L-半胱氨醇 | 139428-96-9

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 氨基醇类衍生物
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: Boc-S-苄基-L-半胱氨醇
• 中文别名: N-叔丁氧羰基-S-苄基-L-半胱氨醇
• 英文名称: Boc-Cys(Bn)-ol
• 英文别名: NH-Boc-S-benzyl-(R)-cysteinol；N-tert-butoxycarbonyl-S-benzyl-(R)-cysteinol；Boc-S-Benzyl-L-cysteinol；tert-butyl N-[(2R)-1-benzylsulfanyl-3-hydroxypropan-2-yl]carbamate
• CAS: 139428-96-9
• 化学式: C₁₅H₂₃NO₃S
• 分子量: 297.419
• InChiKey: MEZQRZMTIJTPIY-CYBMUJFWSA-N

物化性质

• 熔点：
  56-58 °C
• 沸点：
  442.9±40.0 °C(Predicted)
• 密度：
  1.135±0.06 g/cm3(Predicted)
• 溶解度：
  溶于水或1%醋酸

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  83.9
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 危险性防范说明：
  P264,P280,P302+P352,P305+P351+P338,P332+P313,P337+P313,P362
• 危险性描述：
  H315,H319

反应信息

• 作为反应物：
  描述：

  Boc-S-苄基-L-半胱氨醇 在 sodium hydroxide 、 偶氮二甲酸二异丙酯 、 碘 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 6.5h， 生成 (S)-1-((S)-2-Amino-3-benzylsulfanyl-propyldisulfanylmethyl)-2-benzylsulfanyl-ethylamine; compound with trifluoro-acetic acid
  参考文献：
  名称：

  Potent and systemically active aminopeptidase N inhibitors designed from active-site investigation

  摘要：

  Derivatives of amino acids bearing various zinc-coordinating moieties (SH, COOH, CONHOH, and PO3H2) were synthesized and tested for their ability to inhibit aminopeptidase N (APN). Among them, beta-amino thiols were found to be the most efficient with IC50's in the 11-50 nM range. These results suggest that the S1 subsite of APN is a deep but not very large hydrophobic pocket, optimally fitting side chains of moderate bulk endowed with some degree of freedom. The iv administration of the inhibitors, alone, did not induce antinociceptive responses on the hot plate test in mice. However, in presence of 10 mg/kg acetorphan, a prodrug of the neutral endopeptidase inhibitor thiorphan, these compounds gave a large increase in the jump latency time with ED50's of 2 and 2.4 mg/kg for the disulfides of methioninethiol [H2NCH(CH2CH2SCH3)CH2S]2 and S-oxomethioninethiol [H2NCH(CH2CH2S(O)CH3)CH2S]2, respectively. These results show that the disulfide forms of beta-amino thiols are efficient prodrugs of aminopeptidase N inhibitors capable of crossing the blood-brain barrier.

  DOI：

  10.1021/jm00085a013
• 作为产物：
  描述：

  S-苄基-(L)-半胱氨酸甲酯 在 lithium aluminium tetrahydride 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 Boc-S-苄基-L-半胱氨醇
  参考文献：
  名称：

  Synthesis and photophysics of benzazole based triazoles with amino acid-derived pendant units. Multiparametric optical sensors for BSA and CT-DNA in solution

  摘要：

  Herein we report the synthesis of a series of amino acid-derived triazoles by an organocatalytic cycloaddition reaction between azides and carbonyl compounds, catalyzed by a simple amine.These compounds present absorption maxima located in the UV-B ascribed to fully spin and symmetry allowed electronic transitions and a main fluorescence emission in the UV-A (similar to 380 nm) with a relatively large Stokes shift (5700 cm(-1)). No significant solvatochromism was observed in both ground and excited states. Unexpectedly, the benzoxazole derivatives presented much higher fluorescence quantum yield values (40-80%) of compared to the sulfur analogues (3-6%). In addition, the DNA binding assays indicated that these compounds presented strong interaction with CT-DNA, which could be attributed to pi-stacking and intermolecular hydrogen-bonding. The interaction of the benzazoles with bovine serum albumin (BSA) was also investigated, where a suppression mechanism was observed. In each case, docking was performed to better understand the observed interactions. (C) 2020 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molliq.2020.113092

文献信息

• Aminosulf(ox)ides as Ligands for Iridium(I)-Catalyzed Asymmetric Transfer Hydrogenation
  作者：Daniëlle G. I. Petra、Paul C. J. Kamer、Anthony L. Spek、Hans E. Schoemaker、Piet W. N. M. van Leeuwen

  DOI：10.1021/jo991700t

  日期：2000.5.1

  series of chiral N,S-chelates (6-22) was synthesized to serve as ligands in the iridium(I)-catalyzed reduction of ketones. Both formic acid and 2-propanol proved to be suitable as hydrogen donors. Sulfoxidation of an (R)-cysteine-based aminosulfide provided a diastereomeric ligand family containing a chiral sulfur atom. The two chiral centers of these ligands showed a clear effect of chiral cooperativity

  针对不对称酮的不对称转移加氢，开发了一类新型的高效催化剂。合成了一系列手性N，S-螯合物（6-22），用作铱（I）催化的酮还原中的配体。甲酸和2-丙醇均被证明适合作为氢供体。（R）-半胱氨酸基氨基硫化物的磺化氧化提供了包含手性硫原子的非对映体配体家族。这些配体的两个手性中心显示出明显的手性协同作用。另外，合成了在骨架中含有两个不对称碳原子的氨基硫化物。含亚砜的β-氨基醇和源自1的氨基硫化物 2-二取代的氨基醇在各种酮的还原中产生高的反应速率和中等至优异的对映选择性。通过选择最合适的氢供体，有利地影响了反应的对映选择性。在芳基-烷基酮的还原中，达到高达97％的对映选择性。
• New Synthetic Route to <font>γ</font>-Mercaptomethyl PNA Monomers
  作者：Soccorsa Pensato、Luca Domenico D'Andrea、Carlo Pedone、Alessandra Romanelli

  DOI：10.1080/00397910802219122

  日期：2008.7.24

  with an artificial base or by attaching fluorophores to a modified PNA backbone. The need to develop simple protocols to label PNAs encouraged us to design a new procedure for the synthesis of γ-mercaptomethyl-modified PNA. Here we propose a new strategy for the synthesis of modified PNAs, bearing amino acid side chains. The synthesis is straightforward and is an improvement to the procedures reported

  摘要 肽核酸 (PNA) 是一种寡核苷酸模拟物，广泛用作反义、反基因分子和生物技术工具。最近，已经开发了几种基于 PNA 的微阵列和其他生物传感器。用于 DNA 检测的 PNA 分子信标或发光探针的构建需要对 PNA 部分进行标记。标签通常通过柔性接头连接在 C 或 N 末端，或连接在 PNA 序列的中间，用人工碱基替换一个 PNA 碱基或通过将荧光团连接到修饰的 PNA 骨架。开发简单的协议来标记 PNA 的需要鼓励我们设计一种新的程序来合成 γ-巯基甲基修饰的 PNA。在这里，我们提出了一种合成带有氨基酸侧链的修饰 PNA 的新策略。
• Arylaminoethyl amides as noncovalent inhibitors of cathepsin S. Part 2: Optimization of P1 and N-aryl
  作者：Phillip B. Alper、Hong Liu、Arnab K. Chatterjee、KhanhLinh T. Nguyen、David C. Tully、Christine Tumanut、Jun Li、Jennifer L. Harris、Tove Tuntland、Jonathan Chang、Perry Gordon、Thomas Hollenbeck、Donald S. Karanewsky

  DOI：10.1016/j.bmcl.2005.12.056

  日期：2006.3

  A systematic study of anilines led to the discovery of a metabolically robust fluoroindoline replacement for the alkoxy aniline toxicophore in 1. Investigations of the PI pocket resulted in the discovery of a wide tolerance of functionality leading to the discovery of 11 as a potent and selective inhibitor of cathepsin S. (C) 2005 Elsevier Ltd. All rights reserved.
• Exploration of the P1 SAR of aldehyde cathepsin K inhibitors
  作者：John G. Catalano、David N. Deaton、Eric S. Furfine、Annie M. Hassell、Robert B. McFadyen、Aaron B. Miller、Larry R. Miller、Lisa M. Shewchuk、Derril H. Willard、Lois L. Wright

  DOI：10.1016/j.bmcl.2003.09.088

  日期：2004.1

  The synthesis and biological activity of a series of aldehyde inhibitors of cathepsin K are reported. Exploration of the properties of the S(1) subsite with a series of alpha-amino aldehyde derivatives substituted at the P(1) position afforded compounds with cathepsin K IC(50)s between 52 microM and 15 nM.
• One-Pot Synthesis of<b><i>N</i></b>-Protected β-Chiral Amino Alcohols
  作者：Csaba Somlai、Antal Péter、Péter Forgó、Botond Penke

  DOI：10.1081/scc-120020188

  日期：2003.6

  N-tert-butyloxycarbonyl-S-benzyl-cysteine, N-fluorenylmethyloxycarbonyl-alanine-, S-trityl-cysteine-, O-tert-butyl-serine- and O-tert-butyl-tyrosine were converted to the corresponding alcohols via sodium borohydride reduction of their in situ formed methyl esters. Enantiopurity of the products was checked by chiral HPLC method.