85178-37-6

Usage

InChI:InChI=1/C6H9NO2S/c1-9-6(8)4-2-3-5(10)7-4/h4H,2-3H2,1H3,(H,7,10)/t4-/m0/s1

Upstream product

• 67-56-1 methanol 
• 76783-40-9 (S)-5-thioxoproline 
• 4931-66-2 methyl (S)-pyroglutamate 
• 56-86-0 L-glutamic acid 
• 98-79-3 L-Pyroglutamic acid 

Downstream Products

• 908365-68-4 (S)-methyl 5-(1-ethoxy-1,3-dioxo-3-phenylpropan-2-ylidene)pyrrolidine-2-carboxylate 
• 7776-34-3 L-proline hydrochloride 
• 147-85-3 L-proline 
• 2311-25-3 N-acetyl-L-proline methyl ester 

Relevant academic research and scientific papers

Chemoenzymatic synthesis of specifically stable-isotope labelled L-glutamic acid, L-glutamine and L-proline

A synthetic scheme has been developed for the preparation of 13C- or 15N-enriched 2-oxoglutaric acid (1), L-glutamic acid (2), L-glutamine (3) and L-proline (4), from simple and commercially available highly enriched synthons.The products have been obtained with high isotope enrichment (>98percent) and high optical purity on a gram scale.The scheme allows the specific labelling of every C- or N-position and any combination of positions.The used combination of organic synthetic steps and enzymatic steps proves to be a very efficient way to obtain optically active biomolecules.

Synthesis of specially stable-isotope-labeled L-proline via L-glutamic acid

(3,4-(13)C2)-L-proline and ((15)N)-L-proline were prepared from the correspondingly labeled L-glutamic acids via a single scheme in high yield and on a gram scale.The synthetic route is based on the ring closure of L-glutamic acid to L-5-oxoproline and the selective reduction of the 5-amide function, without interference with the 2-carboxylate function and the asymmetric center.The selective reduction is effected by first converting the amide into the corresponding thioamide and subsequently reducing the thioamide to the amine using tributyltin hydride, in combination with protection and deprotection steps.In earlier work we described the preparation of L-glutamic acid isotopically labeled at any position or combination of positions starting from simple highly enriched synthons.The synthetic scheme in this publication makes L-proline, (13)C- or (15)N-labeled at any position or combination of positions, easily available.The labeled L-prolines are charcterized by (1)H-, (13)C- and (15)N-NMR and mass spectrometry.

5-Thioxoproline and 5-Thioxoproline Esters - Synthesis and Crystal Structures

5-Thioxoproline (2a) is synthesized from 5-oxoproline (1a) at room temperature with 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane 2,4-disulfide (3) in DME.The carboxy group requires no protection because of the mild reaction conditions. 5-Thioxoproline esters are synthesized either by thionation of the corresponding 5-oxoproline esters with 3 or by esterification of 2a.Compounds 2a and 5-thioxoproline methyl ester (2b) both crystallize in the space group P212121 with Z=8.Bond lengths and angles in the compounds are compared, and the small differences explained by differences in hydrogen bond pattern.