329191-57-3

Usage

Uses

Used in Pharmaceutical Industry:
(2S,4S)-N^α-Cbz-4-aminoproline benzyl ester is used as a key component in the production of peptide-based drugs. Its controlled addition into peptide chains allows for the creation of specific drug molecules with targeted therapeutic effects.
Used in Research:
In research settings, (2S,4S)-N^α-Cbz-4-aminoproline benzyl ester is utilized for the synthesis of custom peptides and proteins. This enables scientists to design and create novel peptide and protein structures for a wide range of applications, including therapeutic development, diagnostic tools, and fundamental biological studies.

Upstream product

• 13504-85-3 (2S,4R)-1-(benzyloxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid 
• 100-51-6 benzyl alcohol 
• 159551-87-8 (2S,4R)-N^α-Cbz-4-[(p-toluenesulfonyl)oxy]proline benzyl ester 
• 13500-53-3 N-benzyloxycarbonyl-(2S,4R)-4-hydroxyproline benzyl ester 
• 329191-55-1 (2S,4S)-N^α-Cbz-4-azidoproline benzyl ester 
• 81464-46-2 (2S,4S)-4-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-pyrrolidine-1,2-dicarboxylic acid dibenzyl ester 

Downstream Products

• 1000312-50-4 (2S,4S)-4-acetamido-1,2-dibenzyloxycarbonylpyrrolidine 
• 1393739-69-9 6(I)-[N'-(2S,4S)-1,2-dibenzyloxycarbonylpyrrolidin-4-yl]aminocarbonylethylcarbonylamino-6(I)-deoxy-β-cyclodextrin 
• 1352655-90-3 C₂₆H₂₉N₄O₅⁽¹⁺⁾*Cl^(1-) 
• 1352655-92-5 C₂F₆NO₄S₂^(1-)*C₂₆H₂₉N₄O₅⁽¹⁺⁾ 
• 1352655-89-0 N-benzyloxycarbonyl-(2S,4S)-4-(2-chloroacetamido)-proline benzyl ester 
• 1146289-56-6 dibenzyl (2S,4S)-4-(4-methylphenylsulfonamido)pyrrolidine-1,2-dicarboxylate 
• 221352-74-5 (2S,4S)-1-(((9H-fluoren-9-yl)methoxy)carbonyl)-4-(tert-butoxycarbonylamino)pyrrolidine2-carboxylic acid 
• 1279034-78-4 (2S,4S)-4-tert-Butoxycarbonylamino-pyrrolidine-2-carboxylic acid 
• 853063-23-7 (2S,4S)-N^α-Cbz-4-N-Boc-aminoproline benzyl ester 
• 329191-59-5 (2S,4S)-N^α-Cbz-4-N,N'-di-Boc-guanidinoproline benzyl ester 

Relevant academic research and scientific papers

Asymmetric aldol reaction using immobilized proline on mesoporous support

The aldol reaction of hydroxyacetone with different aldehydes using immobilized proline on a mesoporous support, assisted by heat and microwaves, has been explored. It was found that heterogenized L-proline on MCM-41 catalyzed aldol reactions in both hydr

Synthesis and electrophysiological characterization of cyclic morphiceptin analogues

A challenge in opioid peptide chemistry and pharmacology is the possibility to develop novel peptides with peripheral selectivity. An enzymatically stable opioid peptide could involve an antidiarrheal effect. For this reason, we constrained the highly selective and potent tetrapeptide morphiceptin with a 6-atom bridge, resulting in a cyclic amide and an ester analogue, 2 and 3, respectively. Taking advantage of the functional coupling of the opioid receptor with the heteromultimeric G-protein-coupled inwardly rectifying K+ (GIRK1/GIRK2) channel, either the wild-type μ-, κ-, δ- or a mutated μ-opioid receptor (hMORS329A) was functionally co-expressed with GIRK1/GIRK2 channels and a regulator of G-protein signaling (RGS4) in Xenopus laevis oocytes. The two-microelectrode voltage clamp technique was used to measure the opioid receptor activated GIRK1/GIRK2 channel responses. Both cyclic analogues were equally potent via the wild-type μ-opioid receptor hMORwt (EC50 value 976.5±41.7 for 2 and 1017.7±60.7 for 3), while the EC50 value for Tyr-Pro-Phe-D-Pro-NH2 measured 59.3±4.8 nM. These three agonists displayed a four to five times decreased potency via hMORS329A as compared to the wild type. Interestingly, no effect on κ- and δ-opioid receptors was observed. The intramolecular bridge created by cyclization of morphiceptin prevents dipeptidyl peptidase IV from interacting with these analogues. We conclude that constraining morphiceptin with a 6-atom bridge resulted in enzymatically stable peptidomimetics that are exclusively active on μ-opioid receptors. These analogues provide an interesting template in the promising approach for the design of potential antidiarrheal agents.