Fmoc-O-苄基-L-4-羟基脯氨酸 | 174800-02-3

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 脯氨酸类衍生物
• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 中文名称: Fmoc-O-苄基-L-4-羟基脯氨酸
• 中文别名: N-芴甲氧羰基-O-苄基-L-4-羟基脯氨酸
• 英文名称: (2S,4R)-1-(((9H-fluoren-9-yl)methoxy)carbonyl)-4-(benzyloxy)pyrrolidine-2-carboxylic acid
• 英文别名: (2S,4R)-1-(9H-fluoren-9-ylmethoxycarbonyl)-4-phenylmethoxypyrrolidine-2-carboxylic acid
• CAS: 174800-02-3
• 化学式: C₂₇H₂₅NO₅
• 分子量: 443.499
• InChiKey: XGFMHBUVVWZBFT-CLOONOSVSA-N

物化性质

• 沸点：
  640.0±55.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)
• 溶解度：
  溶于氯仿、二氯甲烷、乙酸乙酯、DMSO、丙酮等。

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

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

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  N-叔丁氧羰基-O-苄基-反式-4-羟基-L-脯氨酸	(2S,4R)-4-(benzyloxy)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid	54631-81-1	C17H23NO5	321.373
  9-芴甲基-N-琥珀酰亚胺基碳酸酯	N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide	82911-69-1	C19H15NO5	337.332
  氯甲酸-9-芴基甲酯	(fluorenylmethoxy)carbonyl chloride	28920-43-6	C15H11ClO2	258.704
  Boc-L-羟脯氨酸	(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid	13726-69-7	C10H17NO5	231.249

反应信息

• 作为反应物：
  描述：

  三氟乙酸 、 Fmoc-O-苄基-L-4-羟基脯氨酸 、 6-((S)-1-{[(E)-Allyloxycarbonylimino]-amino-methyl}-3-tert-butoxycarbonylamino-piperidin-2-yloxy)-hexanoic acid 、 alkaline earth salt of/the/ methylsulfuric acid 在 aminomethylated polystyrene resin 作用下， 以17%的产率得到
  参考文献：
  名称：

  Novel protocol for the solid-phase synthesis of peptidyl and peptidomimetic P1-argininal derivatives

  摘要：

  The design, synthesis and application of novel argininal aminals 1 tethered onto AM resin is described. Efficient solid-phase synthesis routes to a wide array of the title derivatives 2 have been implemented using this convenient technology. The resulting P-1-argininal targets serve as useful exploratory scaffolds for serine and cysteine protease inhibitor discovery. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00870-9
• 作为产物：
  描述：

  Boc-L-羟脯氨酸 在 盐酸 、 sodium hydride 、 碳酸氢钠 、 sodium iodide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 丙酮 为溶剂， 生成 Fmoc-O-苄基-L-4-羟基脯氨酸
  参考文献：
  名称：

  Capped dipeptide phenethylamide inhibitors of the HCV NS3 protease

  摘要：

  The N-terminal aminoacid of phenethylamide tripeptide inhibitors of the hepatitis C virus NS3 protease can be replaced with an a-hydroxy acid to obtain more 'drug like' inhibitors with low micromolar activity. The preferred S-configuration of the capping residue can be explained by molecular modeling studies. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.02.032

文献信息

• Macrocyclic inhibitors of the PD-1/PD-L1 and CD80(B7-1)/PD-L1 protein/protein interactions
  申请人：Bristol-Myers Squibb Company

  公开号：US09308236B2

  公开（公告）日：2016-04-12

  The present disclosure provides novel macrocyclic peptides which inhibit the PD-1/PD-L1 and PD-L1/CD80 protein/protein interaction, and thus are useful for the amelioration of various diseases, including cancer and infectious diseases.

  本公开提供了一种新型的大环肽，可以抑制PD-1/PD-L1和PD-L1/CD80蛋白质相互作用，因此对改善包括癌症和传染病在内的各种疾病有用。
• Peptides and their use as inhibitors of hepatitis c virus ns3 protease
  申请人：——

  公开号：US20040142876A1

  公开（公告）日：2004-07-22

  Compounds of formula (I), and pharmaceutically acceptable salts and esters thereof: (I); wherein Q, R2, X, Y and Z are as defined herein; are inhibitors of the hepatitis C virus (HCV) NS3 protease. 1

  式(I)的化合物及其药学上可接受的盐和酯：(I);其中Q，R2，X，Y和Z的定义如下; 是丙型肝炎病毒（HCV）NS3蛋白酶的抑制剂。
• MACROCYCLIC INHIBITORS OF THE PD-1/PD-L1 AND CD80(B7-1)/PD-L1 PROTEIN/PROTEIN INTERACTIONS
  申请人：Bristol-Myers Squibb Company

  公开号：US20140294898A1

  公开（公告）日：2014-10-02

  The present disclosure provides novel macrocyclic peptides which inhibit the PD-1/PD-L1 and PD-L1/CD80 protein/protein interaction, and thus are useful for the amelioration of various diseases, including cancer and infectious diseases.

  本公开提供了新型大环肽，其能够抑制PD-1/PD-L1和PD-L1/CD80蛋白质/蛋白质相互作用，因此可用于改善各种疾病，包括癌症和传染性疾病。
• Novel protocol for the solid-phase synthesis of peptidyl and peptidomimetic P1-argininal derivatives
  作者：Daniel V. Siev、John A. Gaudette、J.Edward Semple

  DOI：10.1016/s0040-4039(99)00870-9

  日期：1999.7

  The design, synthesis and application of novel argininal aminals 1 tethered onto AM resin is described. Efficient solid-phase synthesis routes to a wide array of the title derivatives 2 have been implemented using this convenient technology. The resulting P-1-argininal targets serve as useful exploratory scaffolds for serine and cysteine protease inhibitor discovery. (C) 1999 Elsevier Science Ltd. All rights reserved.
• INHIBITORS OF SERINE PROTEASES, PARTICULARLY HEPATITIS C VIRUS NS3 PROTEASE
  申请人：Tung Roger D.

  公开号：US20090143312A1

  公开（公告）日：2009-06-04

  The present invention relates to compounds, methods and pharmaceutical compositions for inhibiting proteases, particularly serine proteases, and more particularly HCV NS3 proteases. The compounds, and the compositions and methods that utilize them, can be used, either alone or in combination to inhibit viruses, particularly HCV virus.