di-tert-butyl 2,2'-((((2R,2'R)disulfanediylbis(3-methoxy-3-oxopropane-1,2-diyl))bis(azanediyl))bis(carbonyl))(2S,2'S)bis(pyrrolidine-1-carboxylate) | 219655-51-3

• 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: di-tert-butyl 2,2'-((((2R,2'R)disulfanediylbis(3-methoxy-3-oxopropane-1,2-diyl))bis(azanediyl))bis(carbonyl))(2S,2'S)bis(pyrrolidine-1-carboxylate)
• 英文别名: Pro-Cystine-OMe；Boc-Pro-Cys(1)-OMe.Boc-Pro-Cys(1)-OMe；tert-butyl (2S)-2-[[(2R)-1-methoxy-3-[[(2R)-3-methoxy-2-[[(2S)-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carbonyl]amino]-3-oxopropyl]disulfanyl]-1-oxopropan-2-yl]carbamoyl]pyrrolidine-1-carboxylate
• CAS: 219655-51-3
• 化学式: C₂₈H₄₆N₄O₁₀S₂
• 分子量: 662.826
• InChiKey: FEQMXHISRHZZIH-MUGJNUQGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  44
• 可旋转键数：
  17
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  221
• 氢给体数：
  2
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  di-tert-butyl 2,2'-((((2R,2'R)disulfanediylbis(3-methoxy-3-oxopropane-1,2-diyl))bis(azanediyl))bis(carbonyl))(2S,2'S)bis(pyrrolidine-1-carboxylate) 在 盐酸 、 乙酸乙酯 作用下， 生成 NH=Pro-Cys(OMe)-SS-Cys(OMe)-Pro=NH
  参考文献：
  名称：

  A cystine-bearing pseudo-cyclopeptide as a new amphi-receptor

  摘要：

  A conformationally constrained cyclic peptide was designed and synthesized as a novel amphi-receptor. It binds to cations or anions through the carbonyl or amino groups, respectively. The stability of the cation complexes relies largely on the polarizability of the cation, whereas the stability of the anion complexes relies on the strength of the H-bond as well as the polarizability of the anion. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00238-1
• 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 di-tert-butyl 2,2'-((((2R,2'R)disulfanediylbis(3-methoxy-3-oxopropane-1,2-diyl))bis(azanediyl))bis(carbonyl))(2S,2'S)bis(pyrrolidine-1-carboxylate)
  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

• ¹⁸F-Trifluoromethylation of Unmodified Peptides with 5-¹⁸F-(Trifluoromethyl)dibenzothiophenium Trifluoromethanesulfonate
  作者：Stefan Verhoog、Choon Wee Kee、Yanlan Wang、Tanatorn Khotavivattana、Thomas C. Wilson、Veerle Kersemans、Sean Smart、Matthew Tredwell、Benjamin G. Davis、Véronique Gouverneur

  DOI：10.1021/jacs.7b10227

  日期：2018.2.7

  18F-labeling of 5-(trifluoromethyl)-dibenzothiophenium trifluoromethanesulfonate, commonly referred to as the Umemoto reagent, has been accomplished applying a halogen exchange 18F-fluorination with 18F-fluoride, followed by oxidative cyclization with Oxone and trifluoromethanesulfonic anhydride. This new 18F-reagent allows for the direct chemoselective 18F-labeling of unmodified peptides at the thiol cysteine

  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。
• 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。
• 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.