Fmoc-Met-H | 211929-83-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: Fmoc-Met-H
• 英文别名: Fmoc-Met；9H-fluoren-9-ylmethyl N-[(2S)-4-(methylsulfanyl)-1-oxobutan-2-yl]carbamate；9H-fluoren-9-ylmethyl N-[(2S)-4-methylsulfanyl-1-oxobutan-2-yl]carbamate
• CAS: 211929-83-8
• 化学式: C₂₀H₂₁NO₃S
• 分子量: 355.458
• InChiKey: XCABZTKGNAMBJK-AWEZNQCLSA-N

物化性质

• 沸点：
  556.5±50.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 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-Met-H 在 copper(ll) sulfate pentahydrate 、 盐酸羟胺 、 chloroamine-T 、 sodium carbonate 、 sodium ascorbate 作用下， 以 水 、 叔丁醇 为溶剂， 反应 6.0h， 生成
  参考文献：
  名称：

  一种方便的一锅法合成Nα-氨基甲酸酯保护的3-氨基烷基异恶唑5-羧酸及其在制备异恶唑连接的拟肽中的用途

  摘要：

  的Cu（I）催化的[3 + 2]的在原位产生环加成Ñ α -Fmoc /的Boc / Z保护的氨基酸与丙炔酸已经导致了一类新的3,5-二取代的异恶唑轴承氨基酸衍生物烷基氧化腈。本文所述的点击化学方案可有效提供异恶唑嵌入的氨基酸。这些非天然的合成子在N-和C-末端上进行链延伸，以获得带有3，5-二取代的异恶唑的二和三肽类似物。

  DOI：

  10.1007/s10989-011-9256-x
• 作为产物：
  描述：

  Fmoc-L-蛋氨酸 在 草酰氯 、 二甲基亚砜 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 以25%的产率得到Fmoc-Met-H
  参考文献：
  名称：

  Synthesis of 9-fluorenylmethoxycarbonyl-protected amino aldehydes

  摘要：

  9-Fluorenylmethoxycarbonyl-protected amino aldehydes could be efficiently prepared in good yields by using two methods: (i) NaBH4 reduction of Fmoc-protected mixed anhydrides, followed by the Swern oxidation of the alcohols; and (ii) LiAlH4 reduction of Fmoc-protected amino acid Weinreb amides. Both methods afforded comparable overall synthetic yields (70-80%). (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00183-9

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。
• [EN] INHIBITORS<br/>[FR] INHIBITEURS
  申请人：BERGEN TEKNOLOGIOVERFOERING AS

  公开号：WO2019123331A1

  公开（公告）日：2019-06-27

  The present invention relates to compounds having the formula [Co-enzyme A or analogue thereof]-Z1-Z2-Z3-Z4, wherein Z1 is a linker, Z2 and Z3 are peptides or peptide-based moieties, and Z4 is a C-terminal group. The invention also provides pharmaceutical compositions comprising compounds of the invention, and their uses for the treatment of cancer, wound healing and nerve regeneration, inter alia.

  本发明涉及具有以下式的化合物[辅酶A或其类似物]-Z1-Z2-Z3-Z4，其中Z1是连接剂，Z2和Z3是肽或基于肽的基团，Z4是一个C-末端基团。该发明还提供了包括本发明化合物的药物组合物，以及其用于治疗癌症、伤口愈合和神经再生等疾病的用途。
• Discovery of a Novel Class of Potent HCV NS4B Inhibitors: SAR Studies on Piperazinone Derivatives
  作者：Ramesh Kakarla、Jian Liu、Devan Naduthambi、Wonsuk Chang、Ralph T. Mosley、Donghui Bao、Holly M. Micolochick Steuer、Meg Keilman、Shalini Bansal、Angela M. Lam、William Seibel、Sandra Neilson、Phillip A. Furman、Michael J. Sofia

  DOI：10.1021/jm4012643

  日期：2014.3.13

  HTS screening identified compound 2a (piper-azinone derivative) as a low micromolar HCV genotype 1 (GT-1) inhibitor. Resistance mapping studies suggested that this piperazinone chemotype targets the HCV nonstructural protein NS4B. Extensive SAR studies were performed around 2a and the amide function and the C-3/C-6 cis stereochemistry of the piperazinone core were essential for HCV activity. A 10-fold increase in GT-1 potency was observed when the chiral phenylcyclopropyl amide side chain of 2a was replaced with p-fluorophenylisoxazole-carbonyl moiety (67). Replacing the C-6 nonpolar hydrophobic moiety of 67 with a phenyl moiety (95) did not diminish the GT-1 potency. A heterocyclic thiophene moiety (103) and an isoxazole moiety (108) were incorporated as isosteric replacements for the C-6 phenyl moiety (95), resulting in significant improvement in GT-1b and la potency. However, the piperazonone class of compounds lacks GT-2 activity and, consequently, were not pursued further into development.
• Synthesis of <i>C</i>-Protected α-Amino Aldehydes of High Enantiomeric Excess from Highly Epimerizable <i>N</i>-Protected α-Amino Aldehydes
  作者：Andrew G. Myers、Boyu Zhong、Daniel W. Kung、Mohammad Movassaghi、Brian A. Lanman、Soojin Kwon

  DOI：10.1021/ol006427s

  日期：2000.10.1

  [GRAPHICS]A new procedure for the preparation of C-protected alpha-amino aldehydes of high enantiomeric excess is illustrated using five differently substituted alpha-(KFmoc)amino aldehydes as starting materials. Highly epimerization-prone substrates were converted to the corresponding morpholino nitrile-protected alpha-amino aldehydes with minimal racemization (products greater than or equal to 89% ee). Morpholino nitrile derivatives of phenylglycinal were crystallized and subjected to X-ray structural analysis, allowing for definitive determination of the stereochemistry of amino nitrile formation. A rationale for the stereoselectivity of amino nitrile formation is presented.
• Synthesis, biological activity and structure–activity relationship of endomorphin-1/substance P derivatives
  作者：Pegah Varamini、Waleed M. Hussein、Friederike M. Mansfeld、Istvan Toth

  DOI：10.1016/j.bmc.2012.09.003

  日期：2012.11

  Endomorphins have been shown to produce potent analgesia in various rodent models of pain. However, their central administration led to the development of tolerance and physical dependence. Conjugation of C-terminal substance P (SP) fragments to opioids and opioid peptides was previously shown to produce hybrid peptides with strong analgesic activity, with low or no propensity to develop tolerance. In this study, four peptides (2-5) comprised of endomorphin-1 (1) and C-terminal fragments of SP (four or five amino acids, SP8-11 (2) or SP7-11 (4), respectively), with an overlapping Phe residue, were synthesized. To overcome low metabolic stability and poor membrane permeability of the peptide, the N-terminus of 2 and 4 was further modified with a C10-carbon lipoamino acid (C10LAA) achieving 3 and 5, respectively. LAA-modification of the hybrid peptides resulted in a significant increase in metabolic stability and membrane permeability compared to peptides 1,2 and 4. Compound 5 showed potent mu-opioid receptor binding affinity (K-i mu = 3.87 +/- 0.51 nM) with dose-dependent agonist activity in the nanomolar range (IC50 = 45 +/- 13 nM). In silico modeling was used to investigate the binding modes and affinities of compounds 1-5 in the active site of mu-opioid receptors. The docking scores were in agreement with the K-i mu values obtained in the receptor binding affinity studies. The more active LAA-modified hybrid peptide showed a lower total interaction energy and higher negative value of MolDock score. (C) 2012 Elsevier Ltd. All rights reserved.