N_α-(Fluoren-9-ylmethoxycarbonyl)-N_(im)-(tert-butyloxycarbonyl)-L-histidine pentafluorophenyl ester | 109053-20-5

• 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: N_α-(Fluoren-9-ylmethoxycarbonyl)-N_(im)-(tert-butyloxycarbonyl)-L-histidine pentafluorophenyl ester
• 英文别名: N_α-(9-fluorenylmethoxycarbonyl)-N_im-tert-butoxycarbonyl-L-histidine pentafluorophenyl ester；tert-Butyl (S)-4-(2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-oxo-3-(perfluorophenoxy)propyl)-1H-imidazole-1-carboxylate；tert-butyl 4-[(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-oxo-3-(2,3,4,5,6-pentafluorophenoxy)propyl]imidazole-1-carboxylate
• CAS: 109053-20-5
• 化学式: C₃₂H₂₆F₅N₃O₆
• 分子量: 643.567
• InChiKey: LRGNPXMUMGUURS-QFIPXVFZSA-N

物化性质

• 密度：
  1.42±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  46
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  109
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  N_α-(Fluoren-9-ylmethoxycarbonyl)-N_(im)-(tert-butyloxycarbonyl)-L-histidine pentafluorophenyl ester 在 吡啶 、 ammonium hydroxide 、 2-氯-1,3,2-苯并二氧磷杂环己烷-4-酮 、 碘 、 金刚烷酰氯 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 13.75h， 生成 Thymidin-3'-yl N⁶-L-histidyl-6-aminohexyl phosphate
  参考文献：
  名称：

  Synthesis and characterization of imidazoyl-linked synthons and 3'-conjugated thymidine derivatives

  摘要：

  The synthesis of the phosphoramidites and H-phosphonates of imidazoyl derivatives, including histidine and imidazoleacetic acid, blocked at the imidazole and amino groups and connected by a hexane linker arm, are described. These synthons have been used to synthesize novel 3'-conjugated thymidine derivatives using 5'-(dimethoxytrityl)thymidine. These synthons are being used to prepare oligonucleotides with terminal imidazole groups on the automatic synthesizer.

  DOI：

  10.1021/jo00069a022
• 作为产物：
  描述：

  五氟苯酚 、 N_α-(Fluoren-9-ylmethoxycarbonyl)-N_(im)-(tert-butyloxycarbonyl)-L-histidine 在 吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 N_α-(Fluoren-9-ylmethoxycarbonyl)-N_(im)-(tert-butyloxycarbonyl)-L-histidine pentafluorophenyl ester
  参考文献：
  名称：

  Synthesis and characterization of imidazoyl-linked synthons and 3'-conjugated thymidine derivatives

  摘要：

  The synthesis of the phosphoramidites and H-phosphonates of imidazoyl derivatives, including histidine and imidazoleacetic acid, blocked at the imidazole and amino groups and connected by a hexane linker arm, are described. These synthons have been used to synthesize novel 3'-conjugated thymidine derivatives using 5'-(dimethoxytrityl)thymidine. These synthons are being used to prepare oligonucleotides with terminal imidazole groups on the automatic synthesizer.

  DOI：

  10.1021/jo00069a022

文献信息

• α-Ketocarbonyl Peptides:  A General Approach to Reactive Resin-Bound Intermediates in the Synthesis of Peptide Isosteres for Protease Inhibitor Screening on Solid Support
  作者：Alexandra Papanikos、Jörg Rademann、Morten Meldal

  DOI：10.1021/ja003690f

  日期：2001.3.1

  highly reactive terminal ketocarbonyls were prone to aldol-type dimerization and could be transferred into stable moieties by oxime formation, reduction to the alcohol, or reductive amination, respectively. The alpha-ketocarbonyl peptides were efficient in nucleophilic addition of C-nucleophiles such as phosphono-ylides and allylsilanes.

  α-酮羰基肽是通过金属离子催化的转氨作用从固体支持物上的肽前体生成的。反应在 2 小时内完成，乙醛酸盐作为亲电子试剂，铜 (II) 离子作为催化剂，在 pH 5.5-6.0 的醋酸水溶液缓冲液中。各种天然存在的 α-氨基酸底物产生了一组不同的差异功能化酮。高度反应性的末端酮羰基易于发生羟醛型二聚反应，并且可以分别通过肟形成、还原为醇或还原胺化而转化为稳定的部分。α-酮羰基肽在 C-亲核试剂的亲核加成中是有效的，例如膦酰基内酯和烯丙基硅烷。
• Autoxidation of Ascorbic Acid Catalyzed by the Copper(II) Bound to L-Histidine Oligopeptides, (His)iGly and Acetyl-(His)iGly (i=9, 19, 29). Relationship between Catalytic Activity and Coordination Mode.
  作者：Jun-ichi UEDA、Akira HANAKI、Keiichiro HATANO、Terumi NAKAJIMA

  DOI：10.1248/cpb.48.908

  日期：——

  Spectroscopic and kinetic studies on the autoxidation of ascorbic acid catalyzed by copper complexes of histidine oligopeptides, (His)iGly (i=4, 9, 19, 29), and their acetyl derivatives, Ac-(His)iGly (i=9, 19) have been carried out at pH 4.4 and 25 degrees C under dioxygen. The reaction was monitored at 260 nm using a stopped-flow spectrophotometric technique. The reaction fitted the "Michaelis- Menten"

  组氨酸寡肽（His）iGly（i = 4、9、19、29）及其乙酰基衍生物Ac-（His）iGly（i = 9， 19）已经在pH 4.4和25℃在双氧下进行。使用停止流分光光度法在260 nm处监测反应。该反应符合“ Michaelis-Menten”机理，抗坏血酸盐被“ Ping-Pong”机理氧化。与寡肽（i＞或＝ 9）络合的Cu（II）相对于含水Cu（II）使反应增强约两倍。催化活性取决于与组氨酸残基的数目有关的分子量和铜结合位点的配位方式。圆二色性（CD）实验的结果表明存在两种类型的Cu（II）。包含在至少六个组氨酸残基组成的咪唑簇中的具有催化活性的Cu（II），在520和630 nm处显示dd跃迁带，并且易于分解，可增强自氧化作用。Ac-（His）19Gly可能容纳约三个活性Cu（II）离子。与末端H2N-XY-His-部分紧密配合的Cu（II），其中X和Y表示氨基酸，抑制自氧化作用，并在480和550
• Synthesis and characterisation of highly glycosylated glycopeptides with Tn-antigenic structures corresponding to human glycophorin AN
  作者：Gunther Klich、Hans Paulsen、Bernd Meyer、Morten Meldal、Klaus Bock

  DOI：10.1016/s0008-6215(96)00337-0

  日期：1997.3

  Two highly glycosylated O-glycopeptides corresponding to human glycophorin AN with Tn-antigenic structures were synthesised. The first glycopeptide has two glycosylated clusters with three and six adjacent 2-acetamido-2-deoxy-D-galactose (GalNAc) glycosylation sites and represents the N-terminal octadecapeptide from Leu-1 to Lys-18. The second glycopeptide, a decapeptide from His-9 to Lys-18, contains

  合成了两个具有人糖蛋白AN的具有Tn抗原结构的高度糖基化的O-糖肽。第一糖肽具有两个具有三个和六个相邻的2-乙酰氨基-2-脱氧-D-半乳糖（GalNAc）糖基化位点的糖基化簇，并且代表从Leu-1至Lys-18的N-末端八肽。第二个糖肽，即从His-9到Lys-18的十肽，包含6个相邻的GalNAc糖基化位点作为紧密簇。通过使用含碳水化合物的结构单元Fmoc-Ser（Ac3GalN3）-Pfp和Fmoc-Thr（Ac3GalN3）-Pfp实现固相合成。合成的物质通过NMR光谱技术表征。使用的主要技术是同核TOCSY和NOESY以及用于13C，1H相关性的HMQC和HMBC。
• A Solid-Phase Approach to Mouse Melanocortin Receptor Agonists Derived from a Novel Thioether Cyclized Peptidomimetic Scaffold
  作者：Jon Bondebjerg、Zhimin Xiang、Rayna M. Bauzo、Carrie Haskell-Luevano、Morten Meldal

  DOI：10.1021/ja0123913

  日期：2002.9.1

  The solid-phase synthesis of a novel thioether cyclized peptidomimetic scaffold, displaying functionality at the i to i+3 positions, is reported. The thioether bridge is formed on-bead by an intramolecular reaction between a chloroacetylated reduced peptide bond and the free thiol from a cysteine. The crude products were obtained in moderate to very high purity. A series of 19 compounds were prepared and tested for agonist activity at the mouse melanocortin receptors 1, 3, 4, and 5 (mMC1-5R). From these results, several compounds were identified as having low micromolar agonist activity at the mMC1R and mMC4R. The former is involved in skin pigmentation and animal coat coloration. The latter is involved in the regulation of appetite and food intake and is currently a drug target for potential treatment of obesity. The most potent compound 1n with the pharmacophore motif "His-DPhe-Arg-Trp" was identified as having an EC50 value of 165 nM at mMC1R, 7600 nM at mMC3R, 650 nM at mMC4R, and 335 nM at mMC5R. In addition, some of the compounds showed moderate selectivity for the mMC1R.
• ATHERTON, ERIC;CAMERON, LINDA R.;SHEPPARD, ROBERT C., TETRAHEDRON, 44,(1988) N 3, 843-857
  作者：ATHERTON, ERIC、CAMERON, LINDA R.、SHEPPARD, ROBERT C.

  DOI：——

  日期：——