176486-63-8

Usage

Uses

Used in Pharmaceutical Industry:
(2S,4R)-FMOC-4-AMINO-1-BOC-PYRROLIDINE-2-CARBOXYLIC ACID is used as a key intermediate in the synthesis of pharmaceutical compounds, specifically for the preparation of NS3-serine protease inhibitors of hepatitis C virus. These inhibitors play a crucial role in the development of antiviral drugs targeting the hepatitis C virus, as they help to block the viral replication process and reduce the viral load in infected individuals.
Used in Peptide Synthesis:
In the field of peptide chemistry, (2S,4R)-FMOC-4-AMINO-1-BOC-PYRROLIDINE-2-CARBOXYLIC ACID serves as a building block for the synthesis of various peptides and peptide-based drugs. The compound's protected functional groups allow for the stepwise assembly of peptide chains, enabling the creation of complex peptide structures with specific biological activities.
Used in Research and Development:
(2S,4R)-FMOC-4-AMINO-1-BOC-PYRROLIDINE-2-CARBOXYLIC ACID is also utilized in research and development settings, where it can be employed to study the structure-activity relationships of peptides and their analogs. This knowledge can be applied to the design and development of novel therapeutic agents with improved pharmacological properties and reduced side effects.

InChI:InChI=1/C25H28N2O6/c1-25(2,3)33-24(31)27-13-15(12-21(27)22(28)29)26-23(30)32-14-20-18-10-6-4-8-16(18)17-9-5-7-11-19(17)20/h4-11,15,20-21H,12-14H2,1-3H3,(H,26,30)(H,28,29)/t15-,21+/m1/s1

Upstream product

• 82911-69-1 N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide 
• 132622-69-6 (2S,4R)-4-amino-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid 
• 185304-19-2 (2S,4R)-2-benzyl 1-tert-butyl 4-azidopyrrolidine-1,2-dicarboxylate 

Downstream Products

• 862120-41-0 Fmoc-4-amino-2-(1-ethoxycarbonyl-2-vinyl-cyclopropylcarbamoyl)-pyrrolidine-1-carbocyclic acid tert-butyl ester 
• 943134-39-2 (2S,4R)-1-(2-aminoacetyl)-4-benzoylamino-pyrrolidine-2-carboxylic acid 
• 1029683-82-6 C₈₃H₈₂N₁₈O₁₄ 
• 1029683-86-0 C₉₇H₁₀₂N₂₂O₁₈ 
• 1029683-80-4 C₈₃H₈₂N₁₈O₁₄ 
• 1029683-84-8 C₉₇H₁₀₂N₂₂O₁₈ 
• 1029683-83-7 C₈₂H₈₄N₁₆O₁₄ 
• 1029683-87-1 C₉₆H₁₀₄N₂₀O₁₈ 
• 1029683-81-5 C₈₃H₈₂N₁₆O₁₆ 
• 1029683-85-9 C₉₇H₁₀₂N₂₀O₂₀ 
• 1315589-60-6 2-((2S,4R)-4-amino-2-(hydroxymethyl)pyrrolidin-1-yl)-N-(4-((4-((5-methyl-1H-pyrazol-3-yl)amino)pyrrolo[2,1-f][1,2,4]triazin-2-yl)thio)phenyl)acetamide 
• 1558041-05-6 methyl 2-((2S,4R)-1-(benzofuran-3-carbonyl)-4-(1-benzyl-3-ethyl-1H-pyrazole-5-carboxamido)pyrrolidine-2-carboxamido)acetate 
• 1558041-33-0 N-((3R,5S)-1-(benzofuran-3-carbonyl)-5-(ethylcarbamoyl)pyrrolidin-3-yl)-1-methyl-3-phenyl-1H-pyrazole-5-carboxamide 
• 132622-69-6 (2S,4R)-4-amino-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid 

Relevant academic research and scientific papers

INHIBITORS OF PLASMA KALLIKREIN AND USES THEREOF

Provided herein are compounds that inhibit pKal, a serine protease whose activity is responsible for proteolytically cleaving kininogen and generating the potent vasodilator and pro-inflammatory peptide bradykinin, which can lead to painful and debilitating inflammatory attacks (e.g., edema). Also provided are pharmaceutical compositions and kits comprising the compounds, and methods of treating pKal-related diseases and disorders (e.g., edema) with the compounds in a subject, by administering the compounds and/or compositions described herein.

Discovery of subnanomolar arginine-glycine-aspartate-based αvβ3/αvβ5 integrin binders embedding 4-aminoproline residues

The embodiment of 4-aminoproline residues (Amp) into the arginine-glycine-aspartate (RGD) sequence led to the discovery of a novel class of high-affinity αvβ3/αvβ 5 integrin binders [IC50h(αvβ 3) 0.03-5.12 nM; IC50h(αvβ 5) 0.88-154 nM]. A total of eight cyclopeptides of type cyclo-[-Arg-Gly-Asp-Amp-], 5-12, were assembled by a standard solid-phase peptide synthesis protocol that involved the C2-carboxyl and C4-amino functionalities of the proline scaffolds, leaving the Nα- nuclear site untouched. Functionalization of this vacant proline site with either alkyl or acyl substituents proved feasible, with significant benefit to the integrin binding capabilities of the ligands. Notably, six out of eight cyclopeptide inhibitors, 5-7 and 9-11, showed moderate yet significant selectivity toward the αvβ3 receptor. The three-dimensional structure in water was determined by NMR techniques and molecular dynamics calculations. Docking studies to the X-ray crystal structure of the extracellular segment of integrin αvβ3 complexed with reference compound 1 were also performed on selected analogues to highlight the structural features required for potent ligand binding affinity.

NOVEL PEPTIDES AS NS3-SERINE PROTEASE INHIBITORS OF HEPATITIS C VIRUS

The present invention discloses novel peptide compounds which have HCV protease inhibitory activity as well as methods for preparing such compounds. In another embodiment, the invention discloses pharmaceutical compositions comprising such peptides as well as methods of using them to treat disorders associated with the HCV protease.