58640-72-5

Usage

Uses

Used in Structural Biology:
3,4-dehydro-L-proline is used as a building block in the design of peptide-based drugs, contributing to the development of novel therapeutic agents.
Used in Natural Products:
It is found in several natural products, such as the antibiotic massetolide, where it plays a crucial role in the compound's biological activity.
Used in Research:
The challenging production of 3,4-dehydro-L-proline makes it a special area of interest for researchers, who are continuously exploring new methods to synthesize this valuable compound for various applications in the chemical and pharmaceutical industries.

Upstream product

• 634-97-9 pyrrole-2-carboxyl acid 
• 84062-30-6 methyl 1-benzyloxycarbonyl-(4S)-phenylseleno-(2S)-pyrrolidinylcarboxylate 
• 22264-50-2 1-aminocyclobutane-1-carboxylic acid 
• 5211-24-5 (2S)-2,5-dihydro-1H-pyrrole-1,2-dicarboxylic acid 2-methyl 1-(phenylmethyl) ester 
• 1628897-36-8 [Cu^II(bpy)(ACBC)]ClO₄·H₂O 

Downstream Products

• 51077-13-5 N-tert-Butyloxycarbonyl-3,4-dehydro-DL-prolin 
• 1256643-00-1 (2,5-dihydro-1H-pyrrol-2-yl)methanol 
• 135837-63-7 3,4-dehydro-1-(9-fluorenylmethoxycarbonyl)-L-proline 
• 159651-34-0 (1S,2S,5R)-6-oxa-3-aza-bicyclo[3.1.0]hexane-2,3-dicarboxylic acid dibenzyl ester 
• 51077-13-5 N-tert-Butyloxycarbonyl-L-prolin 
• 79680-63-0 N-Tosyl-3,4-dehydro-L-prolin 

Relevant academic research and scientific papers

Oxidative Degradation of Amino Acids and Aminophosphonic Acids by 2,2′-Bipyridine Complexes of Copper(II)

Copper(II)-amino acid (AA) complexes that contain 2,2′-bipyridine (bpy) as supporting ligand were investigated. X-ray structural analysis of three new bpy-based complexes revealed a bidentate coordination of the AAs on the copper(II) centers similar to that proposed for the substrate on the iron(II) center of the 1-aminocyclopropane-1-carboxylic acid oxidase (ACCO). Similar complexes with two aminophosphonic acids (APAs), 1-aminocyclopropane-1-phosphonic acid (ACP) and (1-amino-1-methyl)ethylphosphonic acid (AMEP), were also investigated, and the latter complex was structurally characterized. This structure reveals the bidentate coordination of α-aminophosphonate on the copper(II) ion. The oxidation of the bound amino acids (AAs) and aminophosphonates (APAs), which model the reaction catalyzed by ACCO, was investigated. The complexes react with H2O2 and give oxidation products that were identified by gas chromatography. Reduction of CuII to CuI was detected by UV/Vis spectroscopy upon reaction with H2O2 or ascorbate. This reduction is proposed to be the initial step for the peroxide/copper activation prior to the oxidation of the AA and APA ligands by means of a radical mechanism.

Oxidative degradation of amino acids and aminophosphonic acids by 2,2′-bipyridine complexes of copper(II)

Copper(II)-amino acid (AA) complexes that contain 2,2′-bipyridine (bpy) as supporting ligand were investigated. X-ray structural analysis of three new bpy-based complexes revealed a bidentate coordination of the AAs on the copper(II) centers similar to that proposed for the substrate on the iron(II) center of the 1-aminocyclopropane-1-carboxylic acid oxidase (ACCO). Similar complexes with two aminophosphonic acids (APAs), 1-aminocyclopropane-1- phosphonic acid (ACP) and (1-amino-1-methyl)ethylphosphonic acid (AMEP), were also investigated, and the latter complex was structurally characterized. This structure reveals the bidentate coordination of α-aminophosphonate on the copper(II) ion. The oxidation of the bound amino acids (AAs) and aminophosphonates (APAs), which model the reaction catalyzed by ACCO, was investigated. The complexes react with H2O2 and give oxidation products that were identified by gas chromatography. Reduction of CuII to CuI was detected by UV/Vis spectroscopy upon reaction with H2O2 or ascorbate. This reduction is proposed to be the initial step for the peroxide/copper activation prior to the oxidation of the AA and APA ligands by means of a radical mechanism. The oxidation of bound amino acids or aminophosphonic acids by copper(II) complexes, which models the reaction catalyzed by the 1-aminocyclopropane carboxylic acid oxidase, was investigated in the presence of hydrogen peroxide. A reaction mechanism that involves a CuI intermediate is discussed. Copyright

The preparation of (S)-3,4-dehydroproline from (2S,4R)-4-hydroxyproline

(2S,4R)-N-benzyloxycarbonyl-4-tosyloxyproline methyl ester, readily prepared from commercially available (2S,4R)-N-benzyloxycarbonyl-4-hydroxyproline, was converted to (S)-3,4-dehydroproline of high enantiomeric purity by a process which involved a highly regioselective phenylselenoxide elimination to introduce the olefinic function.

Resolution of D,L-dehydroproline

D,L-3,4-dehydroproline is resolved in high optical yield by conversion to its N-protected derivative, treatment with R(+)alpha-methyl-p-nitrobenzylamine to form the diastereomeric salts, fractional crystallization, decomposition of the L-R salt and regeneration of the secondary amine group. The product L-3,4-dehydroproline obtained in extremely high optical purity is useful as an inhibitor of collagen synthesis.