Fmoc-Cys(Trt)-H | 505076-77-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: Fmoc-Cys(Trt)-H
• 英文别名: Fmoc-Cys(Trt)-OH；9-fluorenylmethoxycarbonyl-Cys(trityl)-OH；(R)-(9H-Fluoren-9-yl)methyl (1-oxo-3-(tritylthio)propan-2-yl)carbamate；9H-fluoren-9-ylmethyl N-[(2R)-1-oxo-3-tritylsulfanylpropan-2-yl]carbamate
• CAS: 505076-77-7
• 化学式: C₃₇H₃₁NO₃S
• 分子量: 569.724
• InChiKey: FEFWRXFCWGLFQX-SSEXGKCCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  42
• 可旋转键数：
  11
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  80.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Fmoc-Cys(Trt)-H 在 吡啶 、 3 A molecular sieve 、 碘 、 sodium cyanoborohydride 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.67h， 生成
  参考文献：
  名称：

  Synthesis of thiol-modified peptide nucleic acids designed for post-assembly conjugation reactions

  摘要：

  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.

  DOI：

  10.1016/j.tet.2006.01.065
• 作为产物：
  描述：

  (R)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-tritylsulfanyl-propionic acid isobutyl ester 在 lithium aluminium tetrahydride 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.17h， 生成 Fmoc-Cys(Trt)-H
  参考文献：
  名称：

  Synthesis of thiol-modified peptide nucleic acids designed for post-assembly conjugation reactions

  摘要：

  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.

  DOI：

  10.1016/j.tet.2006.01.065

文献信息

• 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。
• Enhancement of the helical content and stability induced in a linear oligopeptide by an<b><i>i, i</i>+</b>4 intramolecularly double stapled, overlapping, bicyclic [31, 22, 5]-(<i>E</i>)ene motif
  作者：Daniela Mazzier、Cristina Peggion、Claudio Toniolo、Alessandro Moretto

  DOI：10.1002/bip.22438

  日期：2014.1

  Two consecutive i, i+4 intramolecular, side chain‐to‐side chain, macrocyclizations of different type carried out on a preformed, partially helical peptide result in a largely predominant, double stapled, overlapping, bicyclic [31,22,5]‐(E)ene motif. A detailed ECD and NMR conformational study revealed a significant enhancement of the original helical content and stability, accompanied by an increase

  在一个预先形成的部分螺旋肽上进行两个连续的i，i +4分子内，侧链到侧链的不同类型的大环化反应，从而形成主要占主导地位的双钉，重叠，双环[31,22,5]- （E）ene主题。一项详细的ECD和NMR构象研究表明，原始螺旋含量和稳定性显着提高，并且α-螺旋量比3 10-螺旋量增加。©2013 Wiley Periodicals，Inc.生物高分子（Pept Sci）102：115-123，2014年。
• [EN] BICYCLE TOXIN CONJUGATES AND USES THEREOF<br/>[FR] CONJUGUÉS DE TOXINES BICYCLIQUES ET LEURS UTILISATIONS
  申请人：BICYCLETX LTD

  公开号：WO2020201753A1

  公开（公告）日：2020-10-08

  The present invention relates to Bicycle toxin conjugates, or pharmaceutically acceptable salts thereof, or pharmaceutical compositions thereof, and uses thereof for preventing or treating a disease, disorder, or condition characterised by overexpression of EphA2 in diseased tissue, such as cancer.

  本发明涉及自行车毒素共轭物，或其药用盐，或其药用组合物，以及用于预防或治疗由疾病组织中EphA2过表达所特征的疾病、紊乱或状况的用途，如癌症。
• Therapeutic peptidomimetic macrocycles
  申请人：Nash Huw M.

  公开号：US20090275519A1

  公开（公告）日：2009-11-05

  The present invention provides biologically active peptidomimetic macrocycles for the treatment of cell proliferative disorders such as cancer and immunoproliferative disease.