282729-06-0

Usage

Uses

DL-Proline-2-d1 (CAS# 282729-06-0) is a useful isotopically labeled research compound.

Upstream product

• 86046-10-8 Lithium; (R)-3-tert-butyl-6,7-dihydro-5H-pyrrolo[1,2-c]oxazol-1-olate 
• 344-25-2 D-Prolin 
• 147-85-3 L-proline 
• 609-36-9 rac-Pro-OH 
• 88817-79-2 4,5-dihydropyrrole-1,2-dicarboxylic acid dimethyl ester 
• 84246-56-0 methyl (2S,3S)-5-diazo-4-oxo-N-trifluoroacetyl<2,3-2H₂>norvalinate 
• 152579-95-8 methyl (2S,3R)-[2,3-²H₂]-N-tert-butoxycarbonylpyroglutamate 
• 888948-43-4 methyl (2S,3R)-[2,3-²H₂]-pyroglutamate 
• 152579-97-0 methyl (2S,3R)-[2,3-²H₂]-N-tert-butoxycarbonylprolinate 

Relevant academic research and scientific papers

Asymmetric total synthesis of Lepadiformine C using memory of chirality in an intramolecular ester enolate michael addition

The asymmetric synthesis of lepadiformine C was achieved using D-proline as the only chiral source. The synthetic strategy features the use of the principle of memory of chirality in an intramolecular Michael addition to construct the bicyclic intermediate without the aid of external chiral sources. A brief mechanistic rationale is presented to account for the stereochemical outcome.

Reactivity and selectivity of charged phenyl radicals toward amino acids in a fourier transform ion cyclotron resonance mass spectrometer

The reactivity of 10 charged phenyl radicals toward several amino acids was examined in the gas phase in a dual-cell Fourier transform ion cyclotron resonance mass spectrometer. All radicals abstract a hydrogen atom from the amino acids, as expected. The most electrophilic radicals (with the greatest calculated vertical electron affinities (EA) at the radical site) also react with these amino acids via NH2 abstraction (a nonradical nucleophilic addition-elimination reaction). Both the radical (hydrogen atom abstraction) and nonradical (NH2 abstraction) reaction efficiencies were found to increase with the electrophilicity (EA) of the radical. However, NH2 abstraction is more strongly influenced by EA. In contrast to an earlier report, the ionization energies of the amino acids do not appear to play a general reactivity-controlling role. Studies using several partially deuterium-labeled amino acids revealed that abstraction of a hydrogen atom from the α-carbon is only preferred for glycine; for the other amino acids, a hydrogen atom is preferentially abstracted from the side chain. The electrophilicity of the radicals does not appear to have a major influence on the site from which the hydrogen atom is abstracted. Hence, the regioselectivity of hydrogen atom abstraction appears to be independent of the structure of the radical but dependent on the structure of the amino acid. Surprisingly, abstraction of two hydrogen atoms was observed for the N-(3-nitro-5-dehydrophenyl)pyridinium radical, indicating that substituents on the radical not only influence the EA of the radical but also can be involved in the reaction. In disagreement with an earlier report, proline was found to display several unprecedented reaction pathways that likely do not proceed via a radical mechanism but rather by a nucleophilic addition-elimination mechanism. Both NH2 and 15NH2 groups were abstracted from lysine labeled with 15N on the side chain, indicating that NH2 abstraction occurs both from the amino terminus and from the side chain. Quantum chemical calculations were employed to obtain insights into some of the reaction mechanisms.

Development and Scale-Up of Stereoretentive α-Deuteration of Amines

A stereoretentive deuteration of amino acids and amines has been developed using ruthenium on carbon catalyst, hydrogen gas at atmospheric pressure, and deuterium oxide as a source of deuterium. The process was successfully scaled-up, avoiding the use of expensive and sensitive catalyst and avoiding the use of deuterium gas under pressure. High deuterium incorporation and high yield of labeled compounds were obtained by a simple filtration process.

Enantiospecific C-H Activation Using Ruthenium Nanocatalysts

The activation of C-H bonds has revolutionized modern synthetic chemistry. However, no general strategy for enantiospecific C-H activation has been developed to date. We herein report an enantiospecific C-H activation reaction followed by deuterium incorporation at stereogenic centers. Mechanistic studies suggest that the selectivity for the α-position of the directing heteroatom results from a four-membered dimetallacycle as the key intermediate. This work paves the way to novel molecular chemistry on nanoparticles.

Two separate and distinct syntheses of stereospecifically deuteriated samples of (2S)-proline

Two distinct syntheses of samples of the amino acid l-proline which are stereospecifically deuteriated on the β-carbon atom are reported. In the first of these, the labelled diazoketones 6, prepared by a chemico-enzymatic synthesis, have been photolysed in alkaline conditions to give the corresponding labelled methyl pyroglutamates 10 via hydrolysis and intramolecular trapping of the resultant ketene intermediates 9. These were then converted into (2S,3S)-[3-2H1]- and (2S,3R)-[2,3-2H 2]-proline, 1a and 1b respectively. The second synthesis provides (2S)-[3,3-2H2]-, (2S,3S)- and (2S,3R)-[3- 2H1]-proline, 1d, 1a and 1c respectively, and has as its key step the highly stereoselective hydrolysis of the silylenol ethers 14 and 14a respectively in which deuteriation or protonation occurs from the re-face of the enol ether. The Royal Society of Chemistry 2006.

Ring opening reactions of 1,2-didehydroprolines. Part II. Synthesis of 5-amino-2,4-dihydroxypentanoic acids, their 2-piperidones and pentanolides [1]

NMR spectroscopic investigations on 1,2-didehydroproline in alkaline deuterium oxide revealed incorporation of deuterium at position C-3, presumably due to the presence of acyclic 5-amino-2-oxopentanoate in solution. Reduction of this equilibrium mixture

Deracemisation and stereoinversion of alpha-amino acids using D-amino acid oxidase and hydride reducing agents.

The deracemisation and stereoinversion of both cyclic and acyclic DL-alpha-amino acids, using porcine kidney D-amino acid oxidase (DAAO) and a hydride reducing agent (NaCNBH3-NaBH4), has been investigated.

Simple and efficient preparation of (R)- and (S)-enantiomers of α-carbon deuterium-labelled α-amino acids

A procedure for the synthesis of (R)- and (S)-enantiomers of α-carbon deuterium-labelled α-amino acids, exemplified for (R)- and (S)-[2-2H1]-Leu is described. Starting from the respective (S)- or (R)-enantiomer or from the racemic mixture of an α-amino acid the selective proton exchange at the α-carbon is carried out by racemization via a Schiff base in monodeuterated acetic acid as solvent which serves as deuterium source. After N-protection the racemic mixture is liquid chromatographically separated into the individual (R)- and (S)-enantiomers on preparative scale employing a chiral anion exchanger based on carbamoylated quinine as chiral selector. After deprotection the enantiomerically pure products can be obtained in good yields.

Synthesis of (2S,3S)-[3-2H1]- and (2S,3R)-[2,3-2H2]-proline

Discovery of conditions for intramolecular trapping of a ketene intermediate has led to an effective synthesis of samples of the amino acid proline which are stereospecifically labelled on the β-carbon. Since samples of stereospecifically labelled pyroglutamic acid derivatives are prepared in the route, other stereospecifically labelled, biologically important amino acids may be accessed by the synthesis.

Biosynthesis of Antibiotics of the Virginiamycin Family. 8. Formation of the Dehydroproline Residue

The formation of the dehydroproline residue of the antibiotic virginiamycin M1 occurs with equal facility from both (R)- and (S)-proline; the 3-pro-R proton of proline is lost stereospecifically in this process. cis-3-Hydroxyproline but not trans-3-hydroxyproline is incorporated into the antibiotic, although less efficiently than proline, and virginiamycin M2 is converted into virginiamycin M1.These results suggest that virginiamycin M1 is most probably formed by incorporation of (S)-proline into virginiamycin M2, which then undergoes hydroxylation withretention of configuration and elimination of water to yield virginiamycin M1.