• 1. Synthesis and biological activity of O-glycosylated morphiceptin analogues
  Eduard Bardají,Joseph L. Torres,Pere Clapés,Fernando Albericio,George Barany,Raquel E. Rodríguez,María P. Sacristán,Gregorio Valencia J. Chem. Soc. Perkin Trans. 1 1991 1755

• Solvents and Organic Chemicals Organic Compounds Organic acids and derivatives Carboxylic acids and derivatives Amino acids, peptides, and analogues Amino acids and derivatives
• Solvents and Organic Chemicals Organic Compounds Acids/Esters

Comprehensive Overview of (2S,4R)-1-[(benzyloxy)carbonyl]-4-hydroxypyrrolidine-2-carboxylic acid (CAS No. 13504-85-3)

(2S,4R)-1-[(benzyloxy)carbonyl]-4-hydroxypyrrolidine-2-carboxylic acid (CAS No. 13504-85-3) is a chiral pyrrolidine derivative with significant applications in pharmaceutical chemistry and organic synthesis. This compound, often abbreviated as Cbz-protected 4-hydroxyproline, is a key intermediate in the synthesis of peptides, peptidomimetics, and other bioactive molecules. Its unique stereochemistry and functional groups make it a versatile building block for drug discovery and development.

The growing interest in chiral auxiliaries and asymmetric synthesis has propelled the demand for compounds like (2S,4R)-1-[(benzyloxy)carbonyl]-4-hydroxypyrrolidine-2-carboxylic acid. Researchers and pharmaceutical companies are increasingly exploring its potential in designing enzyme inhibitors, antiviral agents, and anti-inflammatory drugs. The compound's hydroxyl group and carboxylic acid moiety offer multiple sites for chemical modification, enabling the creation of diverse molecular architectures.

One of the most searched questions in the field is: "What is the role of Cbz-protected amino acids in peptide synthesis?" The answer lies in the compound's ability to act as a protecting group for the amine functionality during solid-phase peptide synthesis (SPPS). The benzyloxycarbonyl (Cbz) group is selectively removable under mild conditions, making it ideal for multi-step synthetic routes. This feature is particularly valuable in the production of therapeutic peptides, which are gaining traction in treating metabolic disorders and cancers.

Another trending topic is the use of (2S,4R)-1-[(benzyloxy)carbonyl]-4-hydroxypyrrolidine-2-carboxylic acid in green chemistry and sustainable synthesis. With increasing environmental concerns, chemists are optimizing protocols to minimize waste and energy consumption during its preparation. Recent studies highlight catalytic methods for introducing the Cbz group without hazardous reagents, aligning with the principles of atom economy and reduction of toxic byproducts.

The compound's stereochemical purity is critical for its applications. Analytical techniques like high-performance liquid chromatography (HPLC) and nuclear magnetic resonance (NMR) spectroscopy are routinely employed to verify its enantiomeric excess. This is especially relevant given the rising demand for enantiopure drugs, as regulatory agencies emphasize the importance of chiral integrity in pharmaceutical formulations.

In the context of drug delivery systems, (2S,4R)-1-[(benzyloxy)carbonyl]-4-hydroxypyrrolidine-2-carboxylic acid has been investigated for its potential to enhance bioavailability and targeted release. Its structural motifs are compatible with prodrug strategies, where inactive precursors are metabolized into active compounds in vivo. This approach addresses challenges like poor solubility and rapid clearance, which are common hurdles in drug development.

Future research directions may explore the compound's utility in bioconjugation and nanotechnology. For instance, its carboxylic acid group can be linked to polymeric carriers or nanoparticles for controlled drug release. Such innovations align with the broader trend of personalized medicine, where therapies are tailored to individual patient needs.

In summary, (2S,4R)-1-[(benzyloxy)carbonyl]-4-hydroxypyrrolidine-2-carboxylic acid (CAS No. 13504-85-3) is a multifaceted compound with wide-ranging applications in modern chemistry and medicine. Its relevance to peptide synthesis, green chemistry, and drug delivery underscores its importance in both academic and industrial settings. As scientific advancements continue, this molecule is poised to play an even greater role in addressing global health challenges.

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