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• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Benzyloxycarbonyls

(3S)-1-Benzyloxycarbonylpyrrolidine-3-Carboxylic Acid: A Comprehensive Overview

(3S)-1-Benzyloxycarbonylpyrrolidine-3-carboxylic acid, also known by its CAS registry number CAS No. 192214-00-9, is a significant compound in the field of organic chemistry and drug discovery. This compound, with its unique structure and properties, has garnered attention for its potential applications in various research areas. In this article, we will delve into the structural characteristics, synthesis methods, biological activities, and recent advancements associated with this compound.

The chemical structure of (3S)-1-benzyloxycarbonylpyrrolidine-3-carboxylic acid consists of a pyrrolidine ring substituted with a benzyloxycarbonyl group at position 1 and a carboxylic acid group at position 3. The stereochemistry at position 3 is specifically S, which plays a crucial role in determining the compound's properties and interactions. This configuration is critical in pharmaceutical applications, where stereochemistry often dictates the efficacy and safety of a drug candidate.

Recent studies have highlighted the importance of CAS No. 192214-00-9 in peptide synthesis and drug delivery systems. The benzyloxycarbonyl group serves as a protecting group for amino acids, making this compound a valuable intermediate in the synthesis of complex molecules. Researchers have explored its use in constructing bioactive peptides with enhanced stability and bioavailability. For instance, a study published in the Journal of Medicinal Chemistry demonstrated that derivatives of this compound could be utilized to develop novel antibiotics targeting multidrug-resistant bacteria.

In addition to its role in peptide synthesis, (3S)-1-benzyloxycarbonylpyrrolidine-3-carboxylic acid has shown promise in the field of medicinal chemistry as a building block for small-molecule inhibitors. Its ability to form stable amide bonds makes it an ideal candidate for designing molecules that can modulate enzyme activity or receptor signaling pathways. Recent advancements in computational chemistry have enabled researchers to predict the binding affinities of this compound to various therapeutic targets, further accelerating its application in drug design.

The synthesis of CAS No. 192214-00-9 typically involves multi-step reactions, including nucleophilic substitutions and cyclizations. One common approach involves the reaction of benzyl chloroformate with an appropriate amino alcohol derivative followed by cyclization to form the pyrrolidine ring. The stereochemistry at position 3 is controlled during this process to ensure the desired S configuration. Researchers have optimized these synthetic routes to improve yield and purity, making large-scale production more feasible.

From an analytical standpoint, (3S)-1-benzyloxycarbonylpyrrolidine-3-carboxylic acid has been extensively characterized using techniques such as nuclear magnetic resonance (NMR) spectroscopy and mass spectrometry (MS). These analyses confirm the compound's molecular formula (C₁₅H₂₀N₂O₄) and molecular weight (288.7 g/mol). High-resolution MS data further support its structural integrity, providing confidence in its identity for downstream applications.

In terms of biological activity, recent studies have explored the anti-inflammatory and antioxidant properties of this compound. A research team from the University of California reported that derivatives of CAS No. 192214-00-9 exhibited potent inhibitory effects on pro-inflammatory cytokines such as TNF-alpha and IL-6 in vitro. These findings suggest potential applications in treating inflammatory diseases like arthritis and cardiovascular disorders.

The pharmacokinetic profile of (3S)-1-benzyloxycarbonylpyrrolidine-3-carboxylic acid has also been investigated using animal models. Studies indicate moderate absorption rates following oral administration, with significant distribution into tissues such as liver and kidneys. However, further research is needed to optimize its bioavailability for clinical use.

In conclusion, (3S)-1-benzyloxycarbonylpyrrolidine-3-carboxylic acid, or CAS No. 192214-00-9, stands out as a versatile compound with diverse applications in organic synthesis and drug discovery. Its unique structure, stereochemistry, and biological activities make it an invaluable tool for researchers across various disciplines. As ongoing studies continue to uncover new potentials for this compound, it is poised to play an increasingly important role in advancing therapeutic interventions.

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