81702-31-0

Usage

Uses

Used in Pharmaceutical Development:
2,5-Pyrrolidinedicarboxylic acid, (2S,5S)-(9CI), is used as an intermediate in the synthesis of various pharmaceuticals and biologically active compounds. Its unique structure and properties make it a promising candidate for the development of new drugs and therapeutic agents.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 2,5-Pyrrolidinedicarboxylic acid, (2S,5S)-(9CI), is utilized for its potential applications in the design and synthesis of novel compounds with therapeutic potential. Its unique stereochemistry and functional groups allow for the creation of innovative molecules with specific biological activities.
Used in Materials Science:
2,5-Pyrrolidinedicarboxylic acid, (2S,5S)-(9CI), may also have potential uses in the field of materials science. Its unique structure and properties could be leveraged to develop new materials with specific characteristics, such as improved stability, reactivity, or selectivity.
Used in Organic Synthesis:
In organic synthesis, 2,5-Pyrrolidinedicarboxylic acid, (2S,5S)-(9CI), serves as a valuable building block for the synthesis of complex organic molecules. Its versatile functional groups and unique stereochemistry enable the creation of a wide range of compounds with diverse applications in various industries.

InChI:InChI=1/C6H9NO4/c8-5(9)3-1-2-4(7-3)6(10)11/h3-4,7H,1-2H2,(H,8,9)(H,10,11)/t3-,4-/m0/s1

Upstream product

• 868-72-4 dimethyl (2R,5S)-2,5-dibromohexanedioate 
• 90088-52-1 dimethyl pyrrolidine-2,5-dicarboxylate 
• 51483-87-5 1-Benzyl-2,5-pyrrolidindicarbonsaeure-dimethylester 
• 172879-74-2 ethyl (S)-3,4-dihydro-2H-pyrrole-2-carboxylate 
• 126550-73-0 N-Boc-2-(S)-benzoyloxymethyl-5-(S)-benzyloxy methylpyrrolidine 
• 157968-73-5 (2S,5S)-Pyrrolidine-1,2,5-tricarboxylic acid 1-tert-butyl ester 
• 126550-72-9 (2S,5S)-2-benzyloxymethyl-5-benzoyloxymethylpyrrolidine 
• 138528-06-0 (2S,5S)-5-benzyloxymethyl-1-tert-butoxycarbonyl-2-hydroxymethylpyrrolidine 
• 126550-71-8 (S)-1-benzyloxy-2-benzoylaminohex-5-ene 
• 155418-40-9 (2S)-1-(benzyloxy)hex-5-en-2-ol 
• 126550-70-7 (R)-1-Benzyloxymethyl-pent-4-enylamine 
• 140147-95-1 (5S)-1-methoxycarbonyl-5-(2-methyl-1-propenyl)-L-proline methyl ester 
• 139963-88-5 (5S)-1-methoxycarbonyl-5-formyl-L-proline methyl ester 
• 185385-13-1 1-carbomethoxy-5-methoxy-L-proline methyl ester 

Downstream Products

• 52832-52-7 acido 2-fenil-2,3,5,6,7,7a-esaidro-1-oxo-3-tioxo-1H-pirrolo<1,2-c>imidazolo-5-carbossilico 

Relevant academic research and scientific papers

N-Heterocyclic dicarboxylic acids: Broad-spectrum inhibitors of metallo-β-lactamases with co-antibacterial effect against antibiotic-resistant bacteria

In an effort to identify novel, broad-spectrum inhibitors against the metallo-β-lactamases (MβLs), several N-heterocyclic derivatives were tested as inhibitors of MβLs CcrA, ImiS, and L1, which are representative enzymes from the distinct MβL subclasses. Three N-heterocyclic dicarboxylic acid derivatives were competitive inhibitors of CcrA and L1, exhibiting K i values ≤2 μM, while only 2,4-thiazolidinedicarboxylic acid (1b) was a competitive inhibitor of ImiS. Two 2-mercapto-1,3,4-thiadiazole derivatives were noncompetitive inhibitors of CcrA and ImiS, exhibiting K i values 7 μM; however, these same compounds did not inhibit L1. Two 2-mercapto-1,3,4-triazole derivatives were shown not to inhibit any of the tested MβLs. The N-heterocyclic derivatives were tested for antibacterial activity by examining the MIC values for existing antibiotics in the presence/absence of these derivatives. Consistent with the steady-state inhibition data, the inclusion of three N-heterocyclic dicarboxylic acid derivatives resulted in lower MIC values when using Escherichia coli BL21(DE3) cells containing the CcrA or L1 plasmids or Klebsiella pneumoniae (ATCC 700603), while 1b was the only dicarboxylic acid derivative to lower the MIC value of E. coli cells containing the ImiS plasmid. Inclusion of the 2-mercapto-1,3,4- thiadiazole derivatives resulted in lower MIC values for E. coli cells containing ImiS or L1 plasmids; however, these derivatives did not alter the MIC values for K. pneumoniae or E. coli cells containing the L1 plasmid. None of the N-heterocyclic derivatives affected the MIC of two methicillin resistant Staphylococcus aureus (MRSA) strains. Taken together, these studies demonstrate that N-heterocyclic dicarboxylic acids 1a-c and pyridylmercaptothiadiazoles 2a,b are good scaffolds for future broad-spectrum inhibitors of the MβLs.

Synthesis of Marine Natural Product (2S,5S)-Pyrrolidine-2,5-dicarboxylic Acid

A five-step synthesis of marine natural product (2S,5S)-pyrrolidine-2,5- dicarboxylic acid (1) has been described starting from methyl ester of BOC-protected (S)-proline via stereoselective electrochemical oxidation with introduction of the methoxy group at C5-position by S N2-substitution of the cyano group followed by hydrolysis in 13% overall yield.

An efficient synthesis of substituted prolines by the selective reduction and reductive cyanation of 2-pyrrolidones

Substituted pyrrolidones undergo selective reduction using Cp2ZrHCl (Schwartz's reagent) to form Δ1-pyrrolines, which can be isolated or directly cyanated and hydrolyzed to the corresponding proline. Short syntheses of glutamic semialdehyde (ethyl ester), the marine metabolite (2S,5S)-pyrrolidine-2,5-dicarboxylic acid, and the conformationally constrained amino acid 5,5-dimethylproline, are reported.

A novel method for chirospecific synthesis of 2,5-disubstituted pyrrolidines

One-pot ring formation using (R)-1 or (S)-1 as a nucleophile and homochiral glycidyl triflate (R)-2 or (S)-2 as an electrophile provides a pivotal intermediate 4 which can be transformed into a 2,5-disubstituted pyrrolidine with any desired stereochemistr

A convenient synthesis of enantiomeric pairs of 2,5-disubstituted pyrrolidines of C2-symmetry

By the use of (-)-1-phenylethylamine as a chiral auxiliary, three diastereomeric isomers of 2,5-bis(methoxycarbonyl)pyrrolidine derivatives are prepared from dimethyl rac-2,5-dibromadipate and separted by crystallization and chromatographic fractionation

Short and Efficient Enantioselective Synthesis of cis and trans Pyrrolidine-2,5-dicarboxylic Acids

N-BOC-ethyl pyroglutamate 1 undergoes nucleophilic ring opening with lithium methyl p-tolylsulfinyl anion delivering the p-tolylketosulfoxide 2.Treatment of 2 with TFA gave rise to a mixture of thioesters 3a,3b.The hydrolysis of 3b afforded the (2S,5S) pyrrolidine-2,5-dicarboxylic acid 5, a constituent of the red alga Schizymenia dubyi.Under Pummerer reaction conditions (TFAA/Pyr), 2 yielded the 5-oxo-L-pipecolic acid derivative 6. Key words: Pyroglutamate; Regioselective Reactions; lithium methyl p-tolylsulfinyl anion; 5-carboxy-L-proline; 5-oxo-L-pipecolic acid; Pummerer Reaction.

A short synthesis of C-2 symmetric (2S, 5S) pyrrolidine-2,5 dicarboxylic acid, a constituent of red alga Schizymenia dubyi

(2S, 5S) pyrrolidine-2,5-dicarboxylic acid 1 was synthesized from (5S) N-methoxycarbonyl-5-ethoxyethoxy-methyl pyrrolidin-2-one 2 by a simple and efficient way.

Syntheses of cis- and trans-Pyrrolidine-2,5-dicarboxylic Acids

The syntheses of trans-(2S,5S)- and cis-pyrrolidine-2,5-dicarboxylic acids, in which the key step is the cyclisation of an N-p-tolylsulfonyl-3-oxiranylpropylamine intermediate derived from (S)-but-3-enylglycine, are reported.

Intermolecular Stereoselective Alkenylation of Chiral N-Acylpyrrolidinium Ions

Vinylation of the three cyclic, optically active N-Acylpyrrolidinium ions 5, 8, and 12 with the vinylcopper reagent 2-methyl-1-propenylcopper displays a moderate-to-high trans selectivity with respect to the ring substituents.The absolute configuration of the vinylated products has been confirmed by ozonolysis of the double bond and subsequent degradation to the known amino acids (2S,5S)-pyrrolidine-2,5-dicarboxylic acid, trans-4-hydroxy-L-proline, and trans-3-hydroxy-D-proline.

CONCISE SYNTHESIS OF C2-SYMMETRIC TRANS-2,5-DIOXYMETHYLPYRROLIDINE DERIVATIVES BY NOVEL CYCLIZATION

Treatment of (S)-1-benzyloxy-2-benzoylaminohex-5-ene with iodine in aqueous acetonitrile furnished (2S,5S)-5-benzoyloxymethyl-2-bemzyloxymethylpyrrolidine stereoselectively in a single step.The product was converted into C2-symmetric (2S,5S)-2,5-dioxymethylpyrrolidines potentially utilizable as chiral auxiliaries and (2S,5S)-(-)-pyrrolidine-2,5-dicarboxylic acid isolated from marine alga Schizymenia dubyi.