58640-72-5

Basic information

• Product Name: 3,4-dehydro-L-proline
• Synonyms: H-3,4-dehydro-D-Pro-OH(3,4-dehydro-D-Proline);(2R)-2,5-Dihydro-1H-pyrrole-2-carboxylic acid HCl
• CAS NO: 58640-72-5
• Molecular Formula: C5H7NO2
• Molecular Weight: 113.11458
• Mol File: 58640-72-5.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 279.3±40.0 °C(Predicted)
• Appearance: /
• Density: 1.252±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 2.04±0.20(Predicted)
• CAS DataBase Reference: 3,4-dehydro-L-proline(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-dehydro-L-proline(58640-72-5)
• EPA Substance Registry System: 3,4-dehydro-L-proline(58640-72-5)

Safety Data

• Hazardous Substances Data: 58640-72-5(Hazardous Substances Data)

Usage

General Description

3,4-dehydro-L-proline is a naturally occurring, non-proteinogenic amino acid that is derived from proline, a proteinogenic amino acid. It is known for its unique structure, characterized by a double bond between the third and fourth carbons. This double bond significantly alters the chemical properties compared to standard proline, making it useful in various chemical and biochemical applications. 3,4-dehydro-L-proline is significant in structural biology as it can be utilized in the design of peptide-based drugs. It is also found in several natural products like the antibiotic massetolide. Despite its utility, its production is quite challenging which makes it a special area of interest for researchers.

Upstream product

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

Downstream Products

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

Relevant articles and documents

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 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.