(L)-Fmoc-α-Me-Lys-OH | 1202003-48-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: (L)-Fmoc-α-Me-Lys-OH
• 英文别名: (2S)-6-amino-2-(9H-fluoren-9-ylmethoxycarbonylamino)-2-methylhexanoic acid
• CAS: 1202003-48-2
• 化学式: C₂₂H₂₆N₂O₄
• 分子量: 382.459
• InChiKey: NQAYDUOQKALYFE-QFIPXVFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  102
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  二碳酸二叔丁酯 、 (L)-Fmoc-α-Me-Lys-OH 在 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 、 水 为溶剂， 生成 N6-[叔丁氧羰基]-N2-[芴甲氧羰基]-2-甲基-L-赖氨酸
  参考文献：
  名称：

  Enantioselective synthesis of (L)-Fmoc-α-Me-Lys(Boc)-OH via diastereoselective alkylation of oxazinone as a chiral auxiliary

  摘要：

  Benzyl (2R,3S)-(-)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate (4) was successively alkylated with methyl iodide and 1,4-diiodobutane using a base. In each alkylation step anti-alkylated product formed exclusively. The iodo group was displaced with azide, which served as a precursor for the side-chain amino function. Catalytic hydrogenation with concomitant cleavage of the chiral auxiliary afforded (L)-alpha-Me-Lys-OH (9) in a total of four steps in good yield. (L)-Fmoc-alpha-Me-Lys(Boc)-OH (16) was obtained from 9 via regioselective benzyloxycarbonylation. Alternately, (L)-Fmoc-alpha-Me-Lys(Boc)-OH (16) was obtained via Staudinger reduction of azide (8) in a total of six steps in good yield. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.09.148
• 作为产物：
  描述：

  (L)-Fmoc-α-Me-Lys(Cbz)-OH 在 palladium 10% on activated carbon 、 氢气 作用下， 以73%的产率得到(L)-Fmoc-α-Me-Lys-OH
  参考文献：
  名称：

  Enantioselective synthesis of (L)-Fmoc-α-Me-Lys(Boc)-OH via diastereoselective alkylation of oxazinone as a chiral auxiliary

  摘要：

  Benzyl (2R,3S)-(-)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate (4) was successively alkylated with methyl iodide and 1,4-diiodobutane using a base. In each alkylation step anti-alkylated product formed exclusively. The iodo group was displaced with azide, which served as a precursor for the side-chain amino function. Catalytic hydrogenation with concomitant cleavage of the chiral auxiliary afforded (L)-alpha-Me-Lys-OH (9) in a total of four steps in good yield. (L)-Fmoc-alpha-Me-Lys(Boc)-OH (16) was obtained from 9 via regioselective benzyloxycarbonylation. Alternately, (L)-Fmoc-alpha-Me-Lys(Boc)-OH (16) was obtained via Staudinger reduction of azide (8) in a total of six steps in good yield. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.09.148

文献信息

• [EN] ORAL PEPTIDE INHIBITORS OF INTERLEUKIN-23 RECEPTOR AND THEIR USE TO TREAT INFLAMMATORY BOWEL DISEASES<br/>[FR] PEPTIDES INHIBITEURS PAR VOIE ORALE DU RÉCEPTEUR DE L'INTERLEUKINE-23 ET LEUR UTILISATION DANS LE TRAITEMENT DES MALADIES INFLAMMATOIRES DE L'INTESTIN
  申请人：PROTAGONIST THERAPEUTICS INC

  公开号：WO2016011208A1

  公开（公告）日：2016-01-21

  The present invention provides novel peptide inhibitors of the interleukin-23 receptor, and related compositions and methods of using these peptide inhibitors to treat or prevent a variety of diseases and disorders, including inflammatory bowel disease. In a first aspect, the present invention provides a peptide inhibitor of an interleukin-23 receptor, or a pharmaceutically acceptable salt or solvate thereof, wherein the peptide inhibitor comprises an amino acid sequence of Formula (Xa). In another aspect, the present invention includes a pharmaceutical composition comprising a peptide inhibitor or a peptide dimer inhibitor of the present invention, and a pharmaceutically acceptable carrier.

  本发明提供了新型的干扰素-23受体肽抑制剂，以及相关的组合物和使用这些肽抑制剂来治疗或预防各种疾病和疾病的方法，包括炎症性肠病。在第一个方面，本发明提供了一种干扰素-23受体的肽抑制剂，或其药用盐或溶剂，其中该肽抑制剂包括式（Xa）的氨基酸序列。在另一个方面，本发明包括一种包含本发明的肽抑制剂或肽二聚体抑制剂的药物组合物，以及药用载体。
• TRIAZOLE MACROCYCLE SYSTEMS
  申请人：AILERON THERAPEUTICS, INC.

  公开号：US20160289274A1

  公开（公告）日：2016-10-06

  The present invention provides novel peptidomimetic macrocycles and methods for their preparation and use, as well as amino acid analogs and macrocycle-forming linkers, and kits useful in their production.
• US8637686B2
  申请人：——

  公开号：US8637686B2

  公开（公告）日：2014-01-28
• US9023988B2
  申请人：——

  公开号：US9023988B2

  公开（公告）日：2015-05-05
• Enantioselective synthesis of (L)-Fmoc-α-Me-Lys(Boc)-OH via diastereoselective alkylation of oxazinone as a chiral auxiliary
  作者：Satendra S. Chauhan

  DOI：10.1016/j.tetlet.2009.09.148

  日期：2009.12

  Benzyl (2R,3S)-(-)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate (4) was successively alkylated with methyl iodide and 1,4-diiodobutane using a base. In each alkylation step anti-alkylated product formed exclusively. The iodo group was displaced with azide, which served as a precursor for the side-chain amino function. Catalytic hydrogenation with concomitant cleavage of the chiral auxiliary afforded (L)-alpha-Me-Lys-OH (9) in a total of four steps in good yield. (L)-Fmoc-alpha-Me-Lys(Boc)-OH (16) was obtained from 9 via regioselective benzyloxycarbonylation. Alternately, (L)-Fmoc-alpha-Me-Lys(Boc)-OH (16) was obtained via Staudinger reduction of azide (8) in a total of six steps in good yield. (C) 2009 Elsevier Ltd. All rights reserved.