• 1. An integrated digital microfluidic chip for multiplexed proteomic sample preparation and analysis by MALDI-MS?
  Hyejin Moon,Aaron R. Wheeler,Robin L. Garrell,Chang-Jin “CJ” Kim Lab Chip, 2006,6, 1213-1219
• 2. An aquatic host–guest complex between a supramolecular G-quadruplex and the anticancer drug doxorubicin?
  José M. Rivera,Mariana Martín-Hidalgo,Jean C. Rivera-Ríos Org. Biomol. Chem., 2012,10, 7562-7565
• 3. An artificial CO-releasing metalloprotein built by histidine-selective metallation?
  Inês S. Albuquerque,Hélia F. Jeremias,Miguel Chaves-Ferreira,Dijana Matak-Vinkovic,Omar Boutureira,Carlos C. Rom?o Chem. Commun., 2015,51, 3993-3996
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  Rongning Liang,Tanji Yin,Ruiqing Yao,Wei Qin RSC Adv., 2016,6, 73308-73312
• 5. An Aptamer Bio-barCode (ABC) assay using SPR, RNase H, and probes with RNA and gold-nanorods for anti-cancer drug screening
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• Solvents and Organic Chemicals Organic Compounds Organic acids and derivatives Carboxylic acids and derivatives Amino acids, peptides, and analogues Amino acids and derivatives

Research Briefing on (2S,3aR,7aS)-Octahydroindole-2-carboxylic Acid (CAS: 145438-94-4) and Its Recent Advances

The compound (2S,3aR,7aS)-Octahydroindole-2-carboxylic Acid (CAS: 145438-94-4) is a chiral bicyclic amino acid derivative that has garnered significant attention in the field of chemical biology and pharmaceutical research. With a purity of approximately 90% and containing the cis isomer, this molecule serves as a versatile building block for the synthesis of peptidomimetics and bioactive compounds. Recent studies have explored its potential applications in drug discovery, particularly in the development of protease inhibitors and modulators of protein-protein interactions.

In a 2023 study published in the Journal of Medicinal Chemistry, researchers investigated the use of (2S,3aR,7aS)-Octahydroindole-2-carboxylic Acid as a scaffold for designing novel inhibitors of SARS-CoV-2 main protease (M^pro). The study demonstrated that derivatives of this compound exhibited nanomolar inhibitory activity against M^pro, highlighting its potential as a lead structure for antiviral drug development. The cis configuration of the bicyclic system was found to be critical for maintaining optimal binding affinity to the target enzyme.

Another significant advancement was reported in a 2024 paper in ACS Chemical Biology, where the compound was utilized as a key intermediate in the synthesis of macrocyclic peptides targeting G-protein-coupled receptors (GPCRs). The constrained geometry of the octahydroindole ring system was shown to enhance the conformational stability of the resulting macrocycles, leading to improved pharmacokinetic properties and target selectivity. This work opens new avenues for the development of peptide-based therapeutics with enhanced oral bioavailability.

Recent synthetic methodology developments have also focused on improving the enantioselective preparation of (2S,3aR,7aS)-Octahydroindole-2-carboxylic Acid. A 2023 publication in Organic Letters described a novel asymmetric hydrogenation protocol using a chiral iridium catalyst, achieving >95% enantiomeric excess and significantly higher yields compared to traditional methods. This advancement is particularly important for scaling up production to meet the growing demand for this valuable chiral building block.

In the field of chemical biology, researchers have employed (2S,3aR,7aS)-Octahydroindole-2-carboxylic Acid as a molecular probe to study enzyme mechanisms. Its rigid structure makes it an excellent tool for investigating substrate recognition by various enzymes, particularly those involved in amino acid metabolism. Recent cryo-EM studies have provided atomic-level insights into how this compound interacts with its biological targets, information that is being used to guide rational drug design.

The pharmaceutical industry has shown increasing interest in this compound, with several companies listing it in their catalogs of specialized building blocks for drug discovery. Analytical methods for quality control have been refined, with recent publications detailing improved HPLC and LC-MS protocols for assessing the isomeric purity of (2S,3aR,7aS)-Octahydroindole-2-carboxylic Acid preparations. These developments ensure reliable access to high-quality material for research and development purposes.

Looking forward, the unique structural features of (2S,3aR,7aS)-Octahydroindole-2-carboxylic Acid continue to inspire innovative applications. Current research directions include its incorporation into peptide nucleic acids (PNAs) for gene therapy, development of radiopharmaceuticals for diagnostic imaging, and design of novel enzyme inhibitors for metabolic diseases. The compound's versatility and the recent methodological advances in its synthesis and application suggest it will remain an important tool in chemical biology and medicinal chemistry for years to come.

• 108507-42-2((2R,3aR,7aR)-octahydro-1H-indole-2-carboxylic acid)
• 80828-13-3((2R,3aR,7aR)-rel-OctahydroIndole-2-carboxylic Acid)
• 80875-98-5((2S,3AS,7aS)-Octahydroindole-2-carboxylic acid)
• 145438-95-5((2R,3aR,7aS)-Octahydro-1H-indole-2-carboxylic Acid)
• 130092-20-5(D-Proline,4-cyclohexyl-, (4R)-rel- (9CI))
• 145513-93-5((2S,3aS,7aR)-Octahydro-1H-indole-2-carboxylic Acid)
• 103201-78-1((2S,4S)-4-cyclohexylpyrrolidine-2-carboxylic acid)
• 9002-01-1(Streptokinase)
• 145513-90-2((2S,3aR,7aR)-octahydro-1H-indole-2-carboxylic acid)
• 145513-92-4((2R,3aS,7aR)-Octahydro-1H-indole-2-carboxylic Acid)