188625-66-3

Usage

Uses

Used in Pharmaceutical Industry:
(S)-2-MercaptoMethyl-pyrrolidine-1-carboxylic acid tert-butyl ester is used as a key intermediate in the synthesis of various pharmaceutical compounds due to its unique structural features and reactivity. The thiol group and the protected carboxylic acid functionality allow for the creation of diverse drug candidates with potential therapeutic applications.
Used in Organic Synthesis:
In the field of organic synthesis, (S)-2-MercaptoMethyl-pyrrolidine-1-carboxylic acid tert-butyl ester is utilized as a versatile building block for the development of complex molecular structures. (S)-2-MercaptoMethyl-pyrrolidine-1-carboxylic acid tert-butyl ester's thiol group enables the formation of disulfide bonds and other sulfur-containing functionalities, while the tert-butyl ester group offers protection and stability during synthetic transformations.
Used in Drug Development:
(S)-2-MercaptoMethyl-pyrrolidine-1-carboxylic acid tert-butyl ester holds promise in drug development, as its structural features can be exploited to design novel therapeutic agents. (S)-2-MercaptoMethyl-pyrrolidine-1-carboxylic acid tert-butyl ester's potential pharmacological applications are currently being explored, with a focus on its ability to be selectively modified and incorporated into drug candidates with specific biological activities.

Upstream product

• 73236-85-8 (S)-2-<(acetylthio)methyl>-1-<(tert-butyloxy)carbonyl>pyrrolidine 
• 24424-99-5 di-tert-butyl dicarbonate 
• 132482-09-8 tert-butyl (2S)-2-{[(methylsulfonyl)oxy]methyl}-pyrrolidine-1-carboxylate 
• 23356-96-9 (S)-1-Pyrrolidin-2-yl-methanol 
• 128542-75-6 (S)-2-(bromomethyl)-1-<(tert-butyloxy)carbonyl>pyrrolidine 
• 69610-40-8 N-(tert-butoxycarbonyl)-L-prolinol 

Downstream Products

• 188625-71-0 (S)-2-((3S,4R,5S)-2-Benzyl-5-methyl-3-phenyl-isoxazolidine-4-carbonylsulfanylmethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 188625-70-9 (S)-2-((3S,4R,5S)-5-Methyl-2,3-diphenyl-isoxazolidine-4-carbonylsulfanylmethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester 

Relevant academic research and scientific papers

AMINOPYRIDINE COMPOUNDS AND METHODS FOR THE PREPARATION AND USE THEREOF

The present invention relates generally to therapeutics targeting the bacterium Porphyromonas gingivalis, including its proteases arginine gingipain A/B (Rgp), and their use for the treatment of disorders associated with P. gingivalis infection, including brain disorders such as Alzheimer's disease. In certain embodiments, the invention provides compounds according to Formula I and Formula III, as described herein, and pharmaceutically acceptable salts thereof.

Chemical synthesis of N-peptidyl 2-pyrrolidinemethanethiol for peptide ligation

Peptides carrying a C-terminal 2-pyrrolidinemethanethiol (PMT) unit were synthesized using 9-fluorenylmethoxycarbonyl (Fmoc) solid-phase peptide synthesis (SPPS), and were shown to ligate efficiently with cysteinyl-peptides. This novel PMT-mediated ligation tolerated many different C-terminal residues and was successfully applied to a one-pot N-to-C sequential ligation reaction and the semi-synthesis of lysine 16 acetylated histone H4, demonstrating the utility of the method in peptide and protein synthesis.

Constrained (l-)-S-adenosyl-l-homocysteine (SAH) analogues as DNA methyltransferase inhibitors

Potent SAH analogues with constrained homocysteine units have been designed and synthesized as inhibitors of human DNMT enzymes. The five membered (2S,4S)-4-mercaptopyrrolidine-2-carboxylic acid, in 1a, was a good replacement for homocysteine, while the corresponding six-member counterpart was less active. Further optimization of 1a, changed the selectivity profile of these inhibitors. A Chloro substituent at the 2-position of 1a, compound 1d, retained potency against DNMT1, while N6 alkylation, compound 7a, conserved DNMT3b2 activity. The concomitant substitutions of 1a at both 2- and N6 positions reduced activity against both enzymes.

The synthesis of a new class of oxytocin antagonists

The synthesis of a new class of oxytocin antagonists, with significantly modified C-terminal part, is described. The chemistry of the Mitsunobu reaction was applied to obtain the key derivatives. In spite of the extensive modifications of previously described compound F792, the peptides retain biological activity as oxytocin antagonists.

Homodimeric and heterodimeric bis(amino thiol) oxometal complexes with rhenium(V) and technetium(V). Control of heterodimeric complex formation and an approach to metal complexes that mimic steroid hormones

We have investigated the possibility of preparing complexes of rhenium and technetium whose shape resembles that of ligands for steroid receptors. The general structure of N2S2 complexes of oxorhenium(V) and oxotechnetium(V) is such that they could replace the BC ring system of steroid, thereby generating a metal complex system with considerable size and shape similarity to a steroid. Such a metal-integrated steroid-shaped complex can be constructed as a heterodimer of two different amino thiols; complexes of rhenium and technetium with such heterodimeric bis-bidentate structure have not been systematically studied. In this investigation, we have shown that complexes of this nature form readily when appropriate metal precursors are combined with a mixture of amino thiols. In the systems we have studied, heterodimeric complex formation is preferred over homodimeric complex formation, and in one system where we were able to obtain an X-ray crystal structure, this oxorhenium heterodimer had the desired trans geometry. These rhenium and technetium-99m complexes are reasonably stable toward ligand exchange; they can be readily purified by chromatography under appropriate conditions, and the one technetium-99m complex studied in vivo shows some persistence in blood and gives good initial uptake in several tissues. The convenient and selective formation of such bis-bidentate heterodimeric complexes suggests that the development of metal-integrated complexes that resemble ligands for receptors may be possible.