N-芴甲氧羰基-N-甲基-N-in-叔丁氧羰基-L-色氨酸 | 197632-75-0

• 物质功能分类: 生物化工 - 生化试剂
• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 中文名称: N-芴甲氧羰基-N-甲基-N-in-叔丁氧羰基-L-色氨酸
• 中文别名: 芴甲氧羰基-N-甲基-N‘-叔丁氧羰基-L-色氨酸；N-芴甲氧羰基-N-甲基-N-IN-叔丁氧羰基-L-色氨酸；N-芴甲氧羰基-N-甲基-N'-叔丁氧羰基-L-色氨酸
• 英文名称: 1-[(1,1-dimethylethoxy)carbonyl]-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-N-methyl-L-tryptophan
• 英文别名: Fmoc-NMe-L-Trp(Boc)-OH；Nα-Fmoc-N(in)-Boc-N-methyl-L-tryptophan；Fmoc-L-NMe-Trp(Boc)-OH；Fmoc-N-Me-Trp(Boc)-OH；(2S)-2-[9H-fluoren-9-ylmethoxycarbonyl(methyl)amino]-3-[1-[(2-methylpropan-2-yl)oxycarbonyl]indol-3-yl]propanoic acid
• CAS: 197632-75-0
• 化学式: C₃₂H₃₂N₂O₆
• 分子量: 540.616
• InChiKey: YMZUDCKQUKFBIR-NDEPHWFRSA-N

物化性质

• 沸点：
  710.9±70.0 °C(Predicted)
• 密度：
  1.25

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  40
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  98.1
• 氢给体数：
  1
• 氢受体数：
  6

安全信息

• WGK Germany：
  3
• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H332,H335

制备方法与用途

用途

FMOC-N-ME-TRP(BOC)-OH是一种受保护的N-甲基色氨酸，用于生化试剂、多肽合成。

反应信息

• 作为反应物：
  描述：

  9H-fluoren-9-ylmethyl N-[[2-(3-formylphenyl)phenyl]methyl]carbamate 、 N-alpha-芴甲氧羰基-N-epsilon-叔丁氧羰基-L-赖氨酸 、 N-Fmoc-N'-Boc-L-鸟氨酸 、 N-芴甲氧羰基-N-甲基-N-in-叔丁氧羰基-L-色氨酸 在 N,N-二异丙基乙胺 、 哌啶 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成
  参考文献：
  名称：

  [EN] PEPTIDE MACROCYCLES AND USE THEREOF IN THE TREATMENT OF BACTERIAL INFECTIONS
  [FR] MACROCYCLES PEPTIDIQUES ET LEUR UTILISATION DANS LE TRAITEMENT D'INFECTIONS BACTÉRIENNES

  摘要：

  本发明提供了式（I）的化合物，其中R1，R2，R3，R4，R5，R6，R7，R8，R8'，R9，R9'，X1，X2，X3，X4，X5，X6，X7，X8，X9和X10如本文所述，以及其药学上可接受的盐。此外，本发明涉及式（I）化合物的制造，包含它们的制药组合物以及它们作为药物治疗Acinetobacter baumannii引起的疾病和感染的用途。

  公开号：

  WO2018189063A1
• 作为产物：
  描述：

  甲醇 、 氯甲酸-9-芴基甲酯 、 1-Boc-D-色氨酸 生成 N-芴甲氧羰基-N-甲基-N-in-叔丁氧羰基-L-色氨酸
  参考文献：
  名称：

  Solid phase synthesis of Fmoc N-methyl amino acids: Application of the Fukuyama amine synthesis

  摘要：

  N-Methyl amino acids and their Fmoc derivatives are synthesized in high yield and purity on solid support using the Fukuyama amine synthesis protocol. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)01774-7

文献信息

• [EN] PEPTIDE MACROCYCLES AGAINST ACINETOBACTER BAUMANNII<br/>[FR] MACROCYCLES PEPTIDIQUES CONTRE ACINETOBACTER BAUMANNII
  申请人：HOFFMANN LA ROCHE

  公开号：WO2017072062A1

  公开（公告）日：2017-05-04

  The present invention provides compounds of formula (I) wherein X1 to X8 and R1 to R8 are as described herein, as well as pharmaceutically acceptable salts thereof. Further the present invention is concerned with the manufacture of the compounds of formula (I), pharmaceutical compositions comprising them and their use as medicaments for the treatment of diseases and infections caused by Acinetobacter baumannii.

  本发明提供了式（I）的化合物，其中X1至X8和R1至R8如本文所述，以及其药学上可接受的盐。此外，本发明涉及制备式（I）的化合物，包括它们的药物组合物以及它们作为治疗由鲍曼不动杆菌引起的疾病和感染的药物的用途。
• PEPTIDE MACROCYCLES AGAINST ACINETOBACTER BAUMANNII
  申请人：Hoffmann-La Roche Inc.

  公开号：US20190321440A1

  公开（公告）日：2019-10-24

  The present invention provides compounds of formula (I) wherein X 1 , X 2 , R 1 to R 6 and A are as described herein, as well as pharmaceutically acceptable salts thereof. Further the present invention is concerned with the manufacture of the compounds of formula (I), pharmaceutical compositions comprising them and their use as medicaments for the treatment of diseases and infections caused by bacteria.

  本发明提供了如下式（I）的化合物，其中X1、X2、R1至R6和A如本文所述，并且其药用盐。此外，本发明涉及制备如下式（I）的化合物、包含它们的药物组合物以及将其用作治疗由细菌引起的疾病和感染的药物。
• [EN] GELATINASE INHIBITORS AND USE THEREOF<br/>[FR] INHIBITEURS DES GÉLATINASES ET LEUR UTILISATION
  申请人：IPROTEOS S L

  公开号：WO2017085034A1

  公开（公告）日：2017-05-26

  New gelatinase inhibitors, processes for their preparation, pharmaceutical compositions comprising them, and their use in therapy and/or prophylaxis of conditions wherein inhibition of gelatinases is useful such as epilepsy, schizophrenia, Alzheimer disease, autism (in particular associated to fragile X syndrome), mental retardation, mood disorders such as bipolar disorders, depression, vascular diseases such as ischemic stroke and atherosclerosis, inflammatory diseases such as multiple sclerosis, rheumatoid arthritis and inflammatory bowel disease, drug addiction, neuropathic pain, lung diseases such as asthma and chronic obstructive pulmonary disease, cancer and sepsis.

  新明胶酶抑制剂，其制备方法，包括它们的药物组合物，以及它们在治疗和/或预防明胶酶抑制对疾病有用的情况下的用途，如癫痫、精神分裂症、阿尔茨海默病、自闭症（尤其是与脆性X综合症相关）、智力障碍、情绪障碍如躁郁症、抑郁症、血管疾病如缺血性中风和动脉粥样硬化、炎症性疾病如多发性硬化、类风湿关节炎和炎症性肠病、药物成瘾、神经病性疼痛、肺部疾病如哮喘和慢性阻塞性肺病、癌症和败血症。
• Peptide macrocycles against Acinetobacter baumannii
  申请人：Hoffmann-La Roche Inc.

  公开号：US11505573B2

  公开（公告）日：2022-11-22

  The present invention provides compounds of formula (I) wherein X, L1 and R1 to R10 are as described herein, as well as pharmaceutically acceptable salts thereof. Further the present invention is concerned with the manufacture of the compounds of formula (I), pharmaceutical compositions comprising them and their use as medicaments for the treatment of diseases and infections caused by Acinetobacter baumannii.

  本发明提供了式 (I) 的化合物 其中 X、L1 和 R1 至 R10 如本文所述，以及其药学上可接受的盐类。此外，本发明还涉及式（I）化合物的制造、包含它们的药物组合物以及它们作为治疗鲍曼不动杆菌引起的疾病和感染的药物的用途。
• Investigation of the PDZ domain ligand binding site using chemically modified peptides
  作者：Kathleen A.P Novak、Naoaki Fujii、R.Kiplin Guy

  DOI：10.1016/s0960-894x(02)00345-1

  日期：2002.9

  Several chemically modified analogues to a tightly binding ligand for the second PDZ domain of MAGI-3 were synthesized and evaluated for their ability to compete with native peptide ligands. N-methyl scanning of the ligand backbone amides revealed the energetically important hydrogen bonds between the ligand backbone and the PDZ domain. Analogues to the ligand's conserved threonine/serine(-2) residue, involved in a side chain to side chain hydrogen bond with a conserved histidine in the PDZ domain, revealed that the interaction is highly sensitive to the steric structure around the hydroxyl group of this residue. Analogues of the ligand carboxy terminus revealed that the full hydrogen bond network of the GLGF loop is important in ligand binding. (C) 2002 Elsevier Science Ltd. All rights reserved.