cas 4043-88-3, 3,4-Dehydro-L-proline | Articles data ｜lookchem

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4043-88-3

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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.
Pap, József S.,El Bakkali-Tahéri, Nadia,Fadel, Antoine,Góger, Szabina,Bogáth, Dóra,Molnár, Milán,Giorgi, Michel,Speier, Gábor,Simaan, A. Jalila,Kaizer, József
p. 2829 - 2838
(2015/04/27)

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.
Rueeger, Heinrich,Benn, M. H.
p. 2918 - 2920
(2007/10/02)

AN IMPROVED SYNTHESIS OF S-3,4-DEHYDROPROLINE
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Scott, John W.,Focella, Antonio,Hengartner, Urs O.,Parrish, David R.,Valentine, Donald
p. 529 - 540
(2007/10/02)

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Chemical Properties

Melting Point: 239-241oC (dec.)
Boiling Point: 279.3°Cat760mmHg
Flash Point:122.7°C
Density: 1.252g/cm³
Storage Temp.:-15°C
Vapor Pressure: 0.00108mmHg at 25°C
Refractive Index: 1.4200 (estimate)
PKA: 2.04±0.20(Predicted)
BRN: 5376764
PSA: 49.33000
LogP: -0.07220

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