38533-38-9

Usage

Uses

Used in Pharmaceutical Industry:
(2S,5S)-5-methylpyrrolidine-2-carboxylic acid is used as a key intermediate in the synthesis of Perindopril (P287500), an antihypertensive agent. It plays a crucial role in the development of this medication, which helps in lowering blood pressure and managing hypertension. The specific stereochemistry and structural features of (2S,5S)-5-methylpyrrolidine-2-carboxylic acid contribute to the therapeutic efficacy of Perindopril, making it an essential component in the pharmaceutical industry.

Upstream product

• 1657030-28-8 cis-N-(Boc)-5-methylproline 
• 334769-80-1 (2S,5S)-5-methyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 
• 113400-36-5 benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate 
• 332072-77-2 (S)-(+)-(N-(S)-p-toluenesulfinyl)-2-amino-5,5-(ethelenedioxy)-heptanonitrile 
• 332072-72-7 (S)-(+)-N-[4-(1,3-dioxolan-2-yl)pentanylidene]-p-toluenesulfinamide 
• 24108-29-0 3-(2-methyl-[1,3]dioxolan-2-yl)-propionaldehyde 
• 296774-83-9 methyl 5-oxo-4-(methyloxycarbonyl)-2-[N-(9-phenylfluoren-9-yl)amino]hexanoate 
• 296775-02-5 methyl 5-oxo-2-[N-(9-(9-phenylfluorenyl))amino]hexanoate 
• 2764-43-4 ethyl cis-5-methylpyrrolidine-2-carboxylate 
• 98-79-3 L-Pyroglutamic acid 
• 94885-52-6 benzyl (L)-pyroglutamate 
• 54824-06-5 C₁₃H₁₇NO₂ 
• 113400-46-7 benzyl (2S)-2-[(tert-butoxycarbonyl)amino]-5-oxohexanoate 
• 941-43-5 Ethyl levulinate ethylene ketal 

Downstream Products

• 334769-80-1 (2S,5S)-5-methyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 
• 1033709-37-3 (5S)-1-{[(5R,6S)-5,6-bis(4-chlorophenyl)-3-isopropyl-6-methyl-5,6-dihydroimidazo[2,1-b][1,3]thiazol-2-yl]carbonyl}-N,N,5-trimethyl-L-prolinamide 

Relevant academic research and scientific papers

Activation and Characterization of Bohemamine Biosynthetic Gene Cluster from Streptomyces sp. CB02009

Bohemamines (BHMs) are bacterial alkaloids containing a pyrrolizidine core with two unusual methyl groups. Herein we report the activation of BHMs biosynthesis using a ribosome engineering approach. Characterization of the bhm gene cluster reveals that nonribosomal peptide synthetase BhmJ and Baeyer-Villiger monooxygenase BhmK are responsible for the formation of the pyrrolizidine core, which is further methylated on C-7 by methyltransferase BhmG. The 9-methyl group of BHMs is instead originated from a nonproteinogenic amino acid (2S,5S)-5-methylproline.

Synthesis and evaluation of novel orally active p53-MDM2 interaction inhibitors

We have discovered and reported potent p53-MDM2 interaction inhibitors possessing dihydroimidazothiazole scaffold. Our lead showed strong activity in vitro, but did not exhibit antitumor efficacy in vivo for the low metabolic stability. In order to obtain orally active compounds, we executed further optimization of our lead by the improvement of physicochemical properties. Thus we furnished optimal compounds by introducing an alkyl group onto the pyrrolidine at the C-2 substituent to prevent the metabolism; and modifying the terminal substituent of the proline motif improved solubility. These optimal compounds exhibited good PK profiles and significant antitumor efficacy with oral administration on a xenograft model using MV4-11 cells having wild type p53.

Masked oxo sulfinimines (N-sulfinyl imines) in the asymmetric synthesis of proline and pipecolic acid derivatives.

[structure: see text]. On addition of Et2AlCN/i-PrOH, masked oxo sulfinimines give alpha-amino nitriles that afford oxo alpha-amino acids on hydrolysis. These amino acids cyclize and are reduced to cis proline and cis pipecolic acids derivatives in high ee and good yield. This new procedure avoids many of the limitations related to the preparation of oxo amino acids from proteinogenic amino acids.

Scope and limitations in the use of N-(PhF)serine-derived cyclic sulfamidates for amino acid synthesis

Ring-opening of N-(PhF)serine-derived cyclic sulfamidate 17 was achieved with different nucleophiles (βketo esters, β-keto ketones, dimethyl malonate, nitroethane, sodium azide, imidazole, and potassium thiocyanate) to prepare a variety of amino acid anal