Bis(Fmoc)-cystine | 622832-88-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: Bis(Fmoc)-cystine
• CAS: 622832-88-6
• 化学式: C₃₆H₃₂N₂O₈S
• 分子量: 652.725
• InChiKey: DYEYXZLGIBSQFL-ACHIHNKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  47.0
• 可旋转键数：
  12.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  151.26
• 氢给体数：
  4.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  Bis(Fmoc)-cystine 、 Lys(Boc)-Phe-Trp(Boc)-Trp(Boc)-NH2 在 2-fluoro-1-ethylpyridinium tetrafluoroborate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  Design and synthesis of dimeric HIV-1 integrase inhibitory peptides

  摘要：

  Dimers of known HIV-1 integrase inhibitory hexapeptide H-His-Cys-Lys-Phe-Trp-Trp-NH2 containing different lengths of cross linkers in the place of cysteine residue, were designed, and synthesized. The inhibitory potency of these dimeric peptides is consistently higher than the lead hexapeptide. The dimeric peptide with djenkolic acid linker exhibited IC50 values of 5.3 and 6.5 muM, for 3'-end processing and strand transfer, respectively. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00679-6
• 作为产物：
  描述：

  (Boc-cys-OH)2 在 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 5.0h， 生成 Bis(Fmoc)-cystine
  参考文献：
  名称：

  Design and synthesis of dimeric HIV-1 integrase inhibitory peptides

  摘要：

  Dimers of known HIV-1 integrase inhibitory hexapeptide H-His-Cys-Lys-Phe-Trp-Trp-NH2 containing different lengths of cross linkers in the place of cysteine residue, were designed, and synthesized. The inhibitory potency of these dimeric peptides is consistently higher than the lead hexapeptide. The dimeric peptide with djenkolic acid linker exhibited IC50 values of 5.3 and 6.5 muM, for 3'-end processing and strand transfer, respectively. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00679-6

文献信息

• Glycopeptide Self-Assembly Modulated by Glycan Stereochemistry through Glycan–Aromatic Interactions
  作者：Changdong He、Shuang Wu、Dangliang Liu、Changbiao Chi、Weilin Zhang、Ming Ma、Luhua Lai、Suwei Dong

  DOI：10.1021/jacs.0c06360

  日期：2020.10.7

  other results from spectroscopic, microscopic and rheological experiments, indicate an unusual carbohydrate-aromatic CH-π bonding that promotes glycopeptide self-assembly. These mechanistic findings, particularly evidences obtained at the angstrom scale, illuminate an intriguing role that carbohydrates can play in building supramolecules. Potential biomaterials exploiting the CH-π bond-based stabilization

  碳水化合物通常用于在自组装糖肽中提供亲水性和基于羟基的氢键，提供在生物医学研究中具有广泛适用性的多功能支架。然而，碳水化合物的立体化学如何影响自组装过程仍不清楚。在这里，我们建立了一个二聚体富含酪氨酸的糖肽系统，用于在位点和立体特异性糖基化的影响下探测相应的水凝胶化行为。在 Tyr4 和 Tyr4' 处带有单糖的 18 种糖型的比较表明，当聚糖部分含有轴向羟基时，具有 α-或 β-端基异构体的糖肽表现出相反的胶凝能力。含 β-半乳糖凝胶剂的高分辨率 X 射线晶体结构，以及其他光谱结果，显微和流变学实验表明，一种不寻常的碳水化合物-芳香族 CH-π 键可促进糖肽自组装。这些机械发现，特别是在埃尺度上获得的证据，阐明了碳水化合物在构建超分子中可以发挥的有趣作用。因此，可以开发利用基于 CH-π 键的稳定性的潜在生物材料，例如抗酶水凝胶。
• S-2,4,6-trimethoxybenzyl (Tmob): a novel cysteine protecting group for the N.alpha.-(9-fluorenylmethoxycarbonyl) (Fmoc) strategy of peptide synthesis
  作者：Mark C. Munson、Carlos Garcia-Echeverria、Fernando Albericio、George Barany

  DOI：10.1021/jo00037a013

  日期：1992.5

  The S-2,4,6-trimethoxybenzyl (Tmob) group can be introduced onto sulfhydryl functions from the corresponding alcohol, with acid catalysis, and is in turn removed rapidly by treatment with 30% trifluoroacetic acid-dichloromethane in the presence of phenol, thioanisole, and water (5% each) or 6% trifluoroacetic acid-dichloromethane in the presence of triethylsilane or triisopropylsilane (0.5%). The appropriate cysteine derivative was prepared and applied with other N(alpha)-Fmoc protected amino acids to the solid-phase syntheses of several model peptides. Acidolytic deblocking in the presence of cation scavengers and reducing agents gave the free thiol, whereas oxidative deblocking with iodine or thallium(III) trifluoroacetate provided an intramolecular disulfide. The chemistry of the S-Tmob group compares favorably to established chemistries with the acid-labile and oxidizable S-triphenylmethyl (trityl, Trt) group, as well as with the oxidizable S-acetamidomethyl (Acm) group.