Fmoc-Cys(Trt)-N(CH3)-OCH3 | 370857-83-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: Fmoc-Cys(Trt)-N(CH3)-OCH3
• 英文别名: 9H-fluoren-9-ylmethyl N-[(1R)-1-[methoxy(methyl)carbamoyl]-2-[(triphenylmethyl)sulfanyl]ethyl]carbamate；9H-fluoren-9-ylmethyl N-[(2R)-1-[methoxy(methyl)amino]-1-oxo-3-tritylsulfanylpropan-2-yl]carbamate
• CAS: 370857-83-3
• 化学式: C₃₉H₃₆N₂O₄S
• 分子量: 628.792
• InChiKey: BPQRFVRQWPPXIQ-BHVANESWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  46
• 可旋转键数：
  12
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  93.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Fmoc-Cys(Trt)-N(CH3)-OCH3 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 Fmoc-Cys(Trt)-H
  参考文献：
  名称：

  Synthesis of α, β-unsaturated γ-amino esters with unprecedented high (E)-stereoselectivity and their conformational analysis in peptides

  摘要：

  描述了一种温和、高效且无光学异构化的N保护α, β-不饱和γ-氨基酯的合成方法，该方法具有前所未有的高E型立体选择性。该方法与Boc、Fmoc及其他侧链保护基团相容。研究了单体和同源及混合二肽中乙烯基γ-氨基酯的晶体构象。此外，乙烯基同源二肽显示出β-折叠构象，而混合的α型和α,β-不饱和γ-杂合二肽在单晶中适应了不规则结构。

  DOI：

  10.1039/c1ob05732d
• 作为产物：
  描述：

  Fmoc-S-三苯甲基-L-半胱氨酸 、 N-甲基-N-甲氧基胺盐酸盐 在 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 33.0h， 生成 Fmoc-Cys(Trt)-N(CH3)-OCH3
  参考文献：
  名称：

  固相合成肽乙烯基砜作为半胱氨酸蛋白酶的潜在抑制剂和基于活性的探针。

  摘要：

  由2-氯三苯甲基树脂结合的酚氨基乙烯基乙烯基砜以高收率和纯度制备了肽乙烯基砜。该方法能够方便地合成在P（1）位置具有不同氨基酸的肽乙烯基砜。它还可以有效合成蛋白质组学实验中使用的含乙烯基砜，基于活性的半胱氨酸蛋白酶探针。

  DOI：

  10.1021/ol0275567

文献信息

• Rational Design of a DNA‐Scaffolded High‐Affinity Binder for Langerin
  作者：Gunnar Bachem、Eike‐Christian Wamhoff、Kim Silberreis、Dongyoon Kim、Hannes Baukmann、Felix Fuchsberger、Jens Dernedde、Christoph Rademacher、Oliver Seitz

  DOI：10.1002/anie.202006880

  日期：2020.11.16

  cells for improved therapeutic effect. Since langerin has low affinity for monovalent glycan ligands, highly multivalent presentation has previously been key for targeting. Aiming to reduce the amount of ligand required, we rationally designed molecularly defined high‐affinity binders based on the precise display of glycomimetic ligands (Glc2NTs) on DNA‐PNA scaffolds. Rather than mimicking langerin's

  郎格林结合剂可以将疫苗靶向郎格汉斯细胞，以提高治疗效果。由于兰格林对单价聚糖配体的亲和力较低，因此高度多价的呈递一直是靶向的关键。为了减少所需配体的数量，我们基于 DNA-PNA 支架上糖模拟配体 (Glc2NT) 的精确展示，合理设计了分子定义的高亲和力结合物。我们没有用 C3 对称支架来模仿 langerin 的同源三聚结构，而是开发了易于获取、易于设计的二价结合物。该方法考虑了桥接糖结合位点和统计重新结合的要求，作为加强单个结合位点相互作用并放大螯合提供的亲合力增强的手段。这比游离配体的亲和力净提高了 1150 倍，并为表达 langerin 的细胞特异性内化提供了纳摩尔粘合剂 (IC 50 = 300 nM)。
• General method for the synthesis of cyclic peptidomimetic compounds
  作者：Michael A Walker、Timothy Johnson

  DOI：10.1016/s0040-4039(01)01134-0

  日期：2001.8

  A number of cyclic peptides, wherein the i and i+1 residue side chains are joined by an alkyl linker and a Weinreb amide is present at the C-terminus, were synthesized. Using LiCl to solubilize these peptides in THF the C-terminus can be readily converted to an activated carbonyl such as an aldehyde or ketone. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Synthesis of thiol-modified peptide nucleic acids designed for post-assembly conjugation reactions
  作者：Martijn C. de Koning、Lene Petersen、Jimmy J. Weterings、Mark Overhand、Gijsbert A. van der Marel、Dmitri V. Filippov

  DOI：10.1016/j.tet.2006.01.065

  日期：2006.4

  Two orthogonally protected PNA monomers were prepared having the mercaptomethyl moiety attached to the PNA backbone. These building blocks were employed in solid-phase PNA synthesis and it was shown that Boc/S-p-methoxybenzyl protection scheme was only satisfactory for the introduction of N-terminal thiol modification while the Fmoc/S-butylthio protected monomer proved to be amenable to elongation. The mercaptomethyl modification did not influence the thermal stability of a PNA/RNA duplex. The feasibility of PNA-PNA native ligation was demonstrated. (c) 2006 Elsevier Ltd. All rights reserved.
• Solid-Phase Synthesis of Peptide Vinyl Sulfones as Potential Inhibitors and Activity-Based Probes of Cysteine Proteases
  作者：Gang Wang、Uttamchandani Mahesh、Grace Y. J. Chen、Shao Q. Yao

  DOI：10.1021/ol0275567

  日期：2003.3.1

  Peptide vinyl sulfones were prepared from 2-chlorotrityl resin-bound phenolic amino vinyl sulfones in high yield and purity. This method enables the convenient synthesis of peptide vinyl sulfones having different amino acids at the P(1) position. It also allows efficient synthesis of vinyl sulfone-containing, activity-based probes of cysteine proteases used in a proteomic experiment.

  由2-氯三苯甲基树脂结合的酚氨基乙烯基乙烯基砜以高收率和纯度制备了肽乙烯基砜。该方法能够方便地合成在P（1）位置具有不同氨基酸的肽乙烯基砜。它还可以有效合成蛋白质组学实验中使用的含乙烯基砜，基于活性的半胱氨酸蛋白酶探针。
• Synthesis of α, β-unsaturated γ-amino esters with unprecedented high (E)-stereoselectivity and their conformational analysis in peptides
  作者：Sachitanand M. Mali、Anupam Bandyopadhyay、Sandip V. Jadhav、Mothukuri Ganesh Kumar、Hosahudya N. Gopi

  DOI：10.1039/c1ob05732d

  日期：——

  Mild, efficient and racemization-free synthesis of N-protected α, β-unsaturated γ-amino esters with unprecedented high E- stereoselectivity is described. This method is found to be compatible with Boc-, Fmoc- and other side chain protecting groups. The crystal conformations of the vinylogous γ-amino esters in monomers and in homo- and mixed dipeptides are studied. Further, the vinylogous homo-dipeptide showed a β-sheet conformation, while mixed α- and α,β-unsaturated γ-hybrid dipeptide adapted an irregular structure in single crystals.

  描述了一种温和、高效且无光学异构化的N保护α, β-不饱和γ-氨基酯的合成方法，该方法具有前所未有的高E型立体选择性。该方法与Boc、Fmoc及其他侧链保护基团相容。研究了单体和同源及混合二肽中乙烯基γ-氨基酯的晶体构象。此外，乙烯基同源二肽显示出β-折叠构象，而混合的α型和α,β-不饱和γ-杂合二肽在单晶中适应了不规则结构。