38533-38-9

Basic information

• Product Name: (2S,5S)-5-methylpyrrolidine-2-carboxylic acid
• Synonyms: cis-5-methylproline;(-)-cis-5-Methyl-L-proline
• CAS NO: 38533-38-9
• Molecular Formula: C6H11NO2
• Molecular Weight: 129.15704
• EINECS: -0
• Mol File: 38533-38-9.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (2S,5S)-5-methylpyrrolidine-2-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,5S)-5-methylpyrrolidine-2-carboxylic acid(38533-38-9)
• EPA Substance Registry System: (2S,5S)-5-methylpyrrolidine-2-carboxylic acid(38533-38-9)

Safety Data

• Hazardous Substances Data: 38533-38-9(Hazardous Substances Data)

Usage

Description

(2S,5S)-5-methylpyrrolidine-2-carboxylic acid, also known as (-)-cis-5-Methyl-L-Proline, is a chiral amino acid derivative with a unique cyclic structure and a methyl group at the 5-position. It exhibits specific stereochemistry, with the S-configuration at both the 2nd and 5th carbon atoms. (2S,5S)-5-methylpyrrolidine-2-carboxylic acid is a valuable building block in the synthesis of various pharmaceuticals and biologically active molecules due to its distinctive structural features and chiral properties.

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

• 2764-43-4 ethyl cis-5-methylpyrrolidine-2-carboxylate 
• 1657030-28-8 cis-N-(Boc)-5-methylproline 
• 92012-37-8 cis-N-(Boc)-5-methylproline methyl ester 
• 296775-02-5 methyl 5-oxo-2-[N-(9-(9-phenylfluorenyl))amino]hexanoate 
• 296774-83-9 methyl 5-oxo-4-(methyloxycarbonyl)-2-[N-(9-phenylfluoren-9-yl)amino]hexanoate 
• 24108-29-0 3-(2-methyl-[1,3]dioxolan-2-yl)-propionaldehyde 
• 941-43-5 Ethyl levulinate ethylene ketal 
• 332072-72-7 (S)-(+)-N-[4-(1,3-dioxolan-2-yl)pentanylidene]-p-toluenesulfinamide 
• 332072-77-2 (S)-(+)-(N-(S)-p-toluenesulfinyl)-2-amino-5,5-(ethelenedioxy)-heptanonitrile 
• 113400-36-5 benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate 
• 113400-46-7 benzyl (2S)-2-[(tert-butoxycarbonyl)amino]-5-oxohexanoate 
• 54824-06-5 C₁₃H₁₇NO₂ 
• 94885-52-6 benzyl (L)-pyroglutamate 
• 98-79-3 L-Pyroglutamic acid 

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 articles and documents

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.

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