329012-80-8

Usage

Uses

Used in Scientific Research:
(R)-1-N-Cbz-3-cyanopyrrolidine is used as a research compound for studying its chemical properties and potential interactions with other molecules. Its unique structure and functional groups make it a valuable tool in understanding the behavior of pyrrolidine-based compounds in various chemical reactions and processes.
Used in Pharmaceutical Development:
(R)-1-N-Cbz-3-cyanopyrrolidine is used as a key intermediate in the synthesis of pharmaceutical compounds. Its protective Cbz group and cyano functionality can be strategically utilized in the development of new drugs, particularly in the areas of medicinal chemistry and drug design. (R)-1-N-Cbz-3-cyanopyrrolidine's potential as a precursor in the synthesis of biologically active molecules makes it an important asset in the pharmaceutical industry.
Used in Organic Synthesis:
(R)-1-N-Cbz-3-cyanopyrrolidine is used as a building block in the synthesis of more complex organic molecules. Its presence of a pyrrolidine ring and a cyano group provides a versatile platform for further chemical modifications, allowing for the creation of a wide range of compounds with diverse applications in various industries, including materials science and specialty chemicals.

Upstream product

• 151-50-8 potassium cyanide 
• 158654-83-2 benzyl (3S)-3-(p-tolylsulfonyloxy)pyrrolidine-1-carboxylate 
• 188846-99-3 (+/-)-3-cyanopyrrolidine-1-carboxylic acid benzyl ester 
• 501-53-1 benzyl chloroformate 
• 100858-33-1 (3R)-3-hydroxy-pyrrolidine-1-carboxylic acid benzyl ester 
• 100858-32-0 (S)-3-hydroxy-1-pyrrolidinecarboxylic acid phenylmethyl ester 

Downstream Products

• 192214-06-5 (R)-1-((benzyloxy)-carbonyl)pyrrolidine-3-carboxylic acid 

Relevant academic research and scientific papers

Nitrilase-catalyzed enantioselective synthesis of pyrrolidine- And piperidinecarboxylic acids

The enantioselective synthesis of the nonproteinogenic amino acids β-proline and nipecotic acids from their readily available nitriles is achieved in high enantiomeric excess by commercially available nitrilases. The presented procedure comprises not more than 4 steps, thus considerably reducing the multiple steps generally required. Amide formation is also observed for specific heterocyclic nitriles.

Stability against enzymatic hydrolysis of endomorphin-1 analogues containing β-proline

The enantiomer of endomorphin-1 (Tyr-Pro-Trp-PheNH2) and the analogues containing (S)-or (R)-β-proline have been synthesized, and their affinities towards μ-opioid receptors have been measured. As expected, the incubations of the different peptides with some commercially available enzymes showed that the presence of D-residues gave strong resistance towards digestion. The presence of β-proline alone is sufficient to confer good resistance against the hydrolysis of the biologically strategic Pro-Trp bond.

Synthesis and binding activity of endomorphin-1 analogues β-amino acids

Endomorphin-1 (Tyr-Pro-Trp-PheNH2) has been proposed as the most potent endogenous ligand of the μ-opioid receptors. In this paper, we describe the synthesis of some endomorphin-1 based tetrapeptides in which a residue of the sequence Tyr-Pro-Trp-PheNH2 is replaced by the corresponding β-isomer. These novel peptides showed different affinities for the opioid receptors labeled with [3H]-DAMGO in rat brain membranes, depending on the β-amino acid. In particular, the tetrapeptide containing β-Pro (Tyr-β-(R)-Pro-Trp-PheNH2) displayed a higher affinity than endogenous endomorphin-1, as revealed by their K(i) values (0.33 and 11.1 nM, respectively). (C) 2000 Elsevier Science Ltd.

Constrained β-alanine based GpIIb/IIIa antagonists

The concepts of centrally constrained and peptide based fibrinogen receptor antagonists have been successfully combined into a single series of analogs which have been demonstrated to be potent inhibitors of platelet aggregation.