bis[Boc-Leu-Cys-OMe] | 204383-31-3

• 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
• 英文名称: bis[Boc-Leu-Cys-OMe]
• 英文别名: methyl (6S,9R,14R)-14-((S)-2-((tert-butoxycarbonyl)amino)-4-methylpentanamido)-6-isobutyl-9-(methoxycarbonyl)-2,2-dimethyl-4,7-dioxo-3-oxa-11,12-dithia-5,8-diazapentadecan-15-oate；Leu-Cystine-OMe；Boc-Leu-Cys(1)-OMe.Boc-Leu-Cys(1)-OMe；methyl (2R)-3-[[(2R)-3-methoxy-2-[[(2S)-4-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoyl]amino]-3-oxopropyl]disulfanyl]-2-[[(2S)-4-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoyl]amino]propanoate
• CAS: 204383-31-3
• 化学式: C₃₀H₅₄N₄O₁₀S₂
• 分子量: 694.912
• InChiKey: MUAGPMZYUKRQJF-CMOCDZPBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  46
• 可旋转键数：
  23
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  238
• 氢给体数：
  4
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  bis[Boc-Leu-Cys-OMe] 在 4-二甲氨基吡啶 、 sodium acetate 、 溶剂黄146 、 三苯基膦 作用下， 以 甲醇 、 水 、 二甲基亚砜 为溶剂， 反应 1.67h， 生成 methyl N-((tert-butoxycarbonyl)-L-leucyl)-S-([¹⁸F]trifluoromethyl)-L-cysteinate
  参考文献：
  名称：

  未修饰肽与 5-18F-(三氟甲基)二苯并噻吩三氟甲磺酸盐的 18F-三氟甲基化

  摘要：

  5-(三氟甲基)-二苯并噻吩三氟甲磺酸盐的 18F 标记，通常称为 Umemoto 试剂，已通过卤素交换 18F-氟化与 18F-氟化物，然后与 Oxone 和三氟甲磺酸酐氧化环化来完成。这种新的 18F 试剂允许在硫醇半胱氨酸残基处对未修饰的肽进行直接化学选择性 18F 标记。

  DOI：

  10.1021/jacs.7b10227
• 作为产物：
  描述：

  N,N'-双(叔丁氧羰基)-L-胱氨酸 在 盐酸 、 氯化亚砜 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 为溶剂， 反应 5.25h， 生成 bis[Boc-Leu-Cys-OMe]
  参考文献：
  名称：

  不含内含肽的表达蛋白连接

  摘要：

  具有功能化 C 末端（例如 C 末端硫酯）的蛋白质是通过表达的蛋白质连接合成较大蛋白质的关键。它们通常是通过与内含肽重组融合而制成的。虽然功能强大，但内含肽融合方法存在过早水解和与变性条件的相容性低的问题。为了完全绕过用于表达蛋白连接的酶的参与，我们在这里展示了重组蛋白中的半胱氨酸在其 N 侧酰胺处被小分子氰化试剂化学活化，以进行亲核酰基取代，包括一些胺L-和D-氨基酸和肼。得到的蛋白酰肼可进一步用于表达蛋白的连接。我们通过成功合成泛素偶联物、泛素样蛋白质偶联物、具有 C 端翻译后修饰的组蛋白 H2A、主动水解 RNA 的 RNAse H 和艾塞那肽，证明了这种活化的半胱氨酸定向蛋白连接 (ACPL) 方法的多功能性是一种商业治疗肽。该技术非常简单但非常有用，在很大程度上扩展了蛋白质化学的合成能力，因此将使新的研究成为可能。

  DOI：

  10.1021/jacs.0c00252

文献信息

• Synthesis Of A New Series Of Cyclic Pseudopeptides Containing Pyridine As Backbone Modifier
  作者：Hai Huang、Lin-Jing Mu、Jin-Pei Cheng、Jian-Ming Lu、Xu-Bo Hu

  DOI：10.1080/00397919808004529

  日期：1998.12

  Abstract A new class of cyclic pseudo-peptides which contains pyridine and cystine in the backbone structure was synthesized by a simple three-step preparation. The structures of products were characterized by spectroscopic and conventional analytical methods.

  摘要 通过简单的三步制备方法合成了一类新的主链结构中含有吡啶和胱氨酸的环状假肽。通过光谱和常规分析方法对产物的结构进行表征。
• The role of the disulfide bond in amyloid-like fibrillogenesis in a model peptide system
  作者：Apurba Kumar Das、Michael G. B. Drew、Debasish Haldar、Arindam Banerjee

  DOI：10.1039/b509083k

  日期：——

  Three terminally protected short peptides Bis[Boc-D-Leu1-Cys2-OMe] 1, Bis[Boc-Leu1-Cys2-OMe] and Bis[Boc-Val1-Cys2-OMe] 3 exhibit amyloid-like fibrillar morphology. Single crystal X-ray diffraction analysis of peptide 1 clearly demonstrates that it adopts an overall extended backbone molecular conformation that self-assembles to form an intermolecular hydrogen-bonded antiparallel supramolecular beta-sheet

  三个末端保护的短肽Bis [Boc-D-Leu1-Cys2-OMe] 1，Bis [Boc-Leu1-Cys2-OMe]和Bis [Boc-Val1-Cys2-OMe] 3表现出淀粉样原纤维形态。肽1的单晶X射线衍射分析清楚地表明，它采用了整体扩展的骨架分子构象，该构象自组装以在晶体中形成分子间氢键合的反平行超分子β-折叠结构。扫描电子显微镜（SEM）图像，透射电子显微镜（TEM）图像和刚果红结合研究生动地证明了肽1、2和3的淀粉样样原纤维形成。但是，在肽1、2和3的二硫键还原后3，三个新生成的肽Boc-D-Leu1-Cys2-OMe 4，
• Cystinophanes, a Novel Family of Aromatic-Bridged Cystine Cyclic Peptides:  Synthesis, Crystal Structure, Molecular Recognition, and Conformational Studies
  作者：Darshan Ranganathan、V. Haridas、Isabella L. Karle

  DOI：10.1021/ja9734915

  日期：1998.4.1

  and CD studies have shown these cystinophanes to adopt a β-turn-like structure in solution. X-ray crystal structure of a representative member (3a) containing two aromatic rings has shown a collapsed ring conformation with a near parallel face-to-face orientation of aromatic ringsa feature also suggested by NMR studies. The propensity of cystinocyclophanes to adopt β-turn-type conformation is attributed

  一个新的芳香桥连胱氨酸环肽（胱氨酸）家族已通过一步法合成，包括 1,3 芳香族（Ph 或 Pyr 单元）二羰基二氯与简单的 l-胱氨酸二甲酯缩合，以提供胱氨酸26、39 和 52 元环分别通过 2+2、3+3 和 4+4 环化，或与胱氨酸双肽（H2N-Xaa-Cyst-Xaa-NH2）导致各种1+1 基于胱氨酸的肽环烷。1H NMR 和 CD 研究表明这些胱氨酸在溶液中采用β-转角结构。包含两个芳环的代表性成员 (3a) 的 X 射线晶体结构已显示塌陷的环构象，芳环的面对面取向几乎平行，核磁共振研究也表明了这一特征。Cysinocyclophanes 采用 β 转角型构象的倾向归因于 S-S 键的存在以及需要保持其扭转角的接近正交值。胱氨酸的潜力...
• Ferrocenyl-Bearing Cyclopseudopeptides as Redox-Switchable Cation Receptors
  作者：Hai Huang、Linjing Mu、Jiaqi He、Jin-Pei Cheng

  DOI：10.1021/jo030105v

  日期：2003.10.1

  A family of ferrocenyl-bearing cyclopseudopeptides (1-10) designed for redox-switchable receptors of cations was synthesized. Circular dichroism (CD) and cyclic valtammetry (CV) studies of cation binding properties in both the reduced (K-1) and oxidized (K-2) forms revealed that the binding preference is mainly governed by the charges and radius of the guest cation as well as by the suitability of the host to accommodate the guest. Particularly worth mentioning is the fact that some synthesized cyclopseudopeptides showed high binding affinity and selectivity toward alkaline-earth ions. For example, the K-1 of compound 2 binding with Ca2+ is 4.37 x 10(6) mol(-1).L and its Ca2+/K+ selectivity is 3.1 x 10(1):1, both values are much greater than those of an excellent natural ionophore, valinomycin (1 x 10(5) mol(-1).L and 0.33:1, respectively). The linear relationship between the shifts of half-wave potentials (DeltaE(1/2)) and the radius/charge [r/(+)] ratios suggests that the sensitivity of electrochemical responses to cation complexation be dominated by repulsion factors between the redox center and the incoming cation guest.
• Self-Assembling, Cystine-Derived, Fused Nanotubes Based on Spirane Architecture:  Design, Synthesis, and Crystal Structure of Cystinospiranes
  作者：Darshan Ranganathan、Manoj P. Samant、Isabella L. Karle

  DOI：10.1021/ja0101734

  日期：2001.6.1

  A novel family of cystine-based spirobicyclic peptides (cystinospiranes) has been synthesized by a single-step procedure involving condensation of pentaerythritol-derived tetrachloride with either the simple L-cystine dimethyl ester or its C,C'-extended bispeptides leading to a variety of 19-membered spirobicyclic peptides or its N,N'-extended bispeptides affording the ring-expanded 25-membered cystinospiranes. The design is flexible with respect to the ring size that can be adjusted depending upon the length of the N,N'-extended cystine bispeptide, and the choice of an amino acid, as illustrated here with the preparation of a large number of cystinospiranes containing a wide variety of amino acids. X-ray crystal structure of the parent spirane (5a) revealed nanotube formation by vertical stacking of relatively flat spirobicyclic molecules through contiguous NH- - -O=C hydrogen bonding. The fused pair of parallel nanotubes is open-ended, hollow, and extends to infinity. Crystallographic parameters are the following: C33H52N4O16S4, space group C2, a = 42.181(3) Angstrom, b = 5.1165(7) Angstrom, c = 11.8687(9) Angstrom, beta = 106.23(1)degrees.