35634-41-4

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General Description

2,5-Pyrrolidinedicarboxylic acid, also known as (2R,5S)-rel-(9CI), is a chemical compound with the molecular formula C7H9NO4. It is an organic compound and a derivative of glutamic acid. 2,5-Pyrrolidinedicarboxylicacid,(2R,5S)-rel-(9CI) is a white crystalline solid at room temperature and is soluble in water. It is used in the synthesis of pharmaceuticals, agrochemicals, and other organic compounds. 2,5-Pyrrolidinedicarboxylic acid has potential applications in the fields of medicine and drug development due to its unique chemical properties and structural characteristics.

Upstream product

• 141943-66-0 benzyl 5-hydroxymethyl-1-(p-tolylsulfonyl)pyrrolidine-2-carboxylate 
• 151957-52-7 (S)-2-tert-Butoxycarbonylamino-5-oxo-6-((R)-toluene-4-sulfinyl)-hexanoic acid ethyl ester 
• 144978-35-8 (S)-ethyl N-tert-butoxycarbonylpyroglutamate 
• 649728-59-6 methyl (2S)-N-(tert-butoxycarbonyl)-5R-cyanoprolinecarboxylate 
• 195964-54-6 1-tert-butyl 2-methyl (2S)-5-methoxypyrrolidine-1,2-dicarboxylate 
• 59936-29-7 (S)-N-(tert-butoxycarbonyl)proline methyl ester 
• 116836-63-6 cis-2,5-dimethyl pyrrolidine-2,5-dicarboxylate 
• 51483-87-5 1-Benzyl-2,5-pyrrolidindicarbonsaeure-dimethylester 
• 90088-52-1 dimethyl pyrrolidine-2,5-dicarboxylate 
• 868-72-4 dimethyl (2R,5S)-2,5-dibromohexanedioate 

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

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.

Preparation method of bridge ring compound

The invention provides a preparation method of a bridge ring compound. The preparation method comprises the following steps of S1, using Boc-L-methyl pyroglutamate or Boc-L-ethyl pyroglutamate as a primer, and performing reduction-etherifying reaction on the primer, so as to obtain a first intermediate with a structural formula A; S2, performing substituting reaction on the first intermediate, so as to obtain a second intermediate with a structural formula B; S3, performing hydrolyzing reaction on the second intermediate, so as to obtain a third intermediate with a structural formula C; S4, performing ring-closing reaction on the third intermediate, so as to obtain a fourth intermediate with a structural formula D; S5, performing reduction reaction on the fourth intermediate, so as to obtain the bridge ring compound with a structural formula E, wherein the structural formula A, the structural formula B, the structural formula C, the structural formula D and the structural formula E are respectively shown in the description; R1 is methyl or ethyl; R2 is benzyl, 4-methoxybenzyl, 2,4-dimethoxybenzyl or 3,4-dimethoxybenzyl.

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.

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.

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.