91229-91-3

Usage

Uses

Used in Organic Synthesis:
(S)-N-ALPHA-T-BUTYLOXYCARBONYL-PYROGLUTAMIC ACID T-BUTYL ESTER is used as a protecting group for pyroglutamic acid to facilitate selective reactions at other functional groups within the molecule. This selective protection allows chemists to perform specific transformations without affecting the pyroglutamic acid moiety, enhancing the efficiency and yield of the desired products.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (S)-N-ALPHA-T-BUTYLOXYCARBONYL-PYROGLUTAMIC ACID T-BUTYL ESTER is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its ability to protect the pyroglutamic acid moiety during chemical reactions ensures the integrity and stability of the final drug product, contributing to the development of novel therapeutic agents.
Used in Research and Development:
(S)-N-ALPHA-T-BUTYLOXYCARBONYL-PYROGLUTAMIC ACID T-BUTYL ESTER is utilized in research and development for the study of pyroglutamic acid-containing peptides and proteins. Its protective properties allow researchers to investigate the structure, function, and interactions of these biomolecules without the complications arising from unwanted side reactions.
Used in Peptide Synthesis:
In peptide synthesis, (S)-N-ALPHA-T-BUTYLOXYCARBONYL-PYROGLUTAMIC ACID T-BUTYL ESTER is used as a protecting group for the pyroglutamic acid residue during the assembly of peptide chains. This protection ensures that the pyroglutamic acid moiety remains intact and unreacted during the synthesis process, allowing for the production of peptides with specific sequences and functions.
Overall, (S)-N-ALPHA-T-BUTYLOXYCARBONYL-PYROGLUTAMIC ACID T-BUTYL ESTER is a versatile and essential compound in various applications across the fields of organic chemistry, pharmaceuticals, and research, providing protection and stability to pyroglutamic acid-containing molecules.

InChI:InChI=1/C14H23NO5/c1-13(2,3)19-11(17)9-7-8-10(16)15(9)12(18)20-14(4,5)6/h9H,7-8H2,1-6H3/t9-/m0/s1

Upstream product

• 15761-39-4 1-(tert-butoxycarbonyl)-L-proline 
• 24424-99-5 di-tert-butyl dicarbonate 
• 35418-16-7 L-t-butyl pyroglutamate 
• 113400-36-5 benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate 
• 91237-84-2 N-BOC-proline tert-butyl ester 
• 53100-44-0 L-N-t-butoxycarbonylpyroglutamic acid 
• 94885-52-6 benzyl (L)-pyroglutamate 
• 98-79-3 L-Pyroglutamic acid 
• 540-88-5 acetic acid tert-butyl ester 
• 85136-12-5 (+/-)-tert-butyl 5-oxopyrrolidine-2-carboxylate 
• 90194-99-3 tert-butyl (S)-2-<(tert-butyloxycarbonyl)amino>-5-hydroxypentanoate 
• 1676-73-9 glutamic acid γ-benzyl ester 
• 28812-54-6 α-tert-butyl γ-benzyl N^α-(tert-butyloxycarbonyl)-L-glutamate 
• 24277-39-2 α-tert-butyl N^α-(tert-butyloxycarbonyl)-L-glutamate 

Downstream Products

• 153080-73-0 tert-butyl (2S,4S)-1-(tert-butoxycarbonyl)-4-(cyanomethyl)pyroglutamate 
• 153080-74-1 tert-butyl (2S,4R)-1-(tert-butoxycarbonyl)-4-(cyanomethyl)pyroglutamate 
• 127949-81-9 t-butyl (2S)-1-t-butoxycarbonyl-4-(hydroxyphenylmethyl)pyroglutamate 
• 108732-30-5 (2S)-1-tert-butyloxycarbonyl-4-benzyloxycarbonyl-5-oxoproline tert-butyl ester 
• 228579-90-6 tert-butyl (2S)-(1-tert-butoxycarbonyl)-5-hydroxypyrrolidine-2-carboxylate 
• 151121-34-5 di-tert-butyl (2S,4E)-4-[(dimethylamino)methylidene]-5-oxopyrrolidine-1,2-dicarboxylate 
• 208520-00-7 (S)-2-tert-butoxycarbonylamino-6-diazo-5-oxohexanoic acid tert-butyl ester 
• 138858-47-6 tert-butyl (2S,4S)-N-(tert-butoxycarbonyl)-4-benzylpyroglutamate 
• 144345-38-0 (2S,4S)-di-tert-butyl 4-methyl-5-oxopyrrolidine-1,2-dicarboxylate 
• 206119-91-7 (2S,4R)-4-methyl-5-oxopyrrolidine-1,2-dicarboxylic acid di-tert-butyl ester 
• 260269-91-8 tert-butyl (2S)-2-(N-tert-butyloxycarbonyl)amino-5-[3-(4-chloropyridinyl)]-5-oxopentanoate 

Relevant academic research and scientific papers

An efficient synthetic route tol-γ-methyleneglutamine and its amide derivatives, and their selective anticancer activity

In cancer cells, glutaminolysis is the primary source of biosynthetic precursors, fueling the TCA cycle with glutamine-derived α-ketoglutarate. The enhanced production of α-ketoglutarate is critical to cancer cells as it provides carbons for the TCA cycle to produce glutathione, fatty acids, and nucleotides, and contributes nitrogens to produce hexosamines, nucleotides, and many nonessential amino acids. Efforts to inhibit glutamine metabolism in cancer using amino acid analogs have been extensive.l-γ-Methyleneglutamine was shown to be of considerable biochemical importance, playing a major role in nitrogen transport inArachisandAmorphaplants. Herein we report for the first time an efficient synthetic route tol-γ-methyleneglutamine and its amide derivatives. Many of thesel-γ-methyleneglutamic acid amides were shown to be as efficacious as tamoxifen or olaparib at arresting cell growth among MCF-7 (ER+/PR+/HER2?), and SK-BR-3 (ER?/PR?/HER2+) breast cancer cells at 24 or 72 h of treatment. Several of these compounds exerted similar efficacy to olaparib at arresting cell growth among triple-negative MDA-MB-231 breast cancer cells by 72 h of treatment. None of the compounds inhibited cell growth in benign MCF-10A breast cells. Overall,N-phenyl amides andN-benzyl amides, such as3,5,9, and10, arrested the growth of all three (MCF-7, SK-BR-3, and MDA-MB-231) cell lines for 72 h and were devoid of cytotoxicity on MCF-10A control cells;N-benzyl amides with an electron withdrawing group at theparaposition, such as5and6, inhibited the growth of triple-negative MDA-MB-231 cells commensurate to olaparib. These compounds hold promise as novel therapeutics for the treatment of multiple breast cancer subtypes.

L-Y-METHYLENEGLUTAMINE COMPOUNDS AND METHODS OF USE

Disclosed are substantially pure L-y-methyleneglutamine, L-y- methyleneglutamic acid, and/or amide derivatives, and methods of use thereof. In particular, the presently disclosed subject matter relates to L-y-methyleneglutamine, L-y-methyleneglutamic acid, and/or amide derivatives thereof, and methods of treating cancer. The method comprises administering one or more substantially pure L-y-methyleneglutamine, L-y-methyleneglutamic acid, and/or amide derivatives to a subject in need thereof.

MASP INHIBITORY COMPOUNDS AND USES THEREOF

The present invention relates to novel Mannose-binding lectin (MBL)-associated serine protease (MASP) inhibitory compounds, as well as analogues and derivatives thereof, to processes for the preparation thereof, to the use thereof alone or in combinations for treatment and/or prevention of diseases and to the use thereof for production of medicaments for treatment and/or prevention of diseases, especially for treatment and/or prevention of renal and cardiovascular disorders and of ischemia reperfusion injuries.

A Stereoselective Synthesis of the ACE Inhibitor Trandolapril

A conceptually novel and stereoselective synthesis of the enantiopure octahydroindole building block and its conversion into the ACE inhibitor trandolapril was achieved. Key steps include the α-allylation of a protected l -pyroglutamic acid derivative, a highly diastereoselective Hosomi-Sakurai reaction and a Ru-catalyzed ring-closing metathesis of a 4,5-diallylated proline. This way, the synthesis of trandolapril was efficiently achieved in 25% overall yield (12 steps).

Design and Synthesis of Building Blocks for PPII-Helix Secondary-Structure Mimetics: A Stereoselective Entry to 4-Substituted 5-Vinylprolines

In the course of our studies towards the synthesis of proline-based secondary-structure mimetics, we developed a straightforward methodology for the diastereoselective preparation of 4-alkyl-5-vinyl-substituted proline derivatives. Starting from N-Boc-protected tert-butyl pyroglutamate, α-alkylation, lactam reduction and acid-catalyzed methanolysis afforded 4-alkyl-5-methoxyproline derivatives. After BF3-induced formation of an N-acyl-iminium intermediate, the introduction of the 5-vinyl side chain was achieved with high diastereoselectivity by using vinylmagnesium bromide in the presence of AlCl3 or CuBr·SMe2 to afford either the cis- or the trans-product, respectively. The utility of the method was demonstrated in the rapid and efficient construction of new diproline mimetics rigidified in a polyproline-type II helix (PPII) conformation.

INHIBITORS FOR INHIBITING TUMOR METASTASIS

The present invention relates to chemical compounds that can in particular be used as structural mimetics of proline-rich peptides. The compounds of the present invention are capable of selectively inhibiting ena/VASP-EVH1-mediated protein-protein interactions. The invention further relates to the use of said compounds as pharmaceutical agents and to the use of the pharmaceutical agents to treat tumor diseases. The chemical compounds of the present invention can significantly inhibit the chemotaxis and motility of invasive tumor cells and can therefore be used in the treatment and/or prevention of tumor metastases.

HEPATITIS C VIRUS INHIBITORS

The present invention discloses compounds of Formula (I), and pharmaceutically acceptable salts, esters, or prodrugs thereof: (structurally represented), which inhibit RNA-containing virus, particularly the hepatitis C virus (HCV). Consequently, the compounds of the present invention interfere with the life cycle of the hepatitis C virus and are also useful as antiviral agents. The present invention further relates to pharmaceutical compositions comprising the aforementioned compounds for administration to a subject suffering from HCV infection. The invention also relates to methods of treating an HCV infection in a subject by administering a pharmaceutical composition comprising the compounds of the present invention.

HETEROARYL PYRIDONE AND AZA-PYRIDONE AMIDE COMPOUNDS

Heteroaryl pyridone and aza-pyridone amide compounds of Formula (I) are provided, and various substituents including stereoisomers, tautomers, and pharmaceutically acceptable salts thereof, useful for inhibiting Btk, and for treating cancer and immune disorders such as inflammation mediated by Btk. Methods of using compounds of Formula I for in vitro, in situ, and in vivo diagnosis, and treatment of such disorders in mammalian cells, or associated pathological conditions, are disclosed.

The revisited synthesis of tert-butyl pyroglutamate derivatives

The very common protection reactions of scaffolds by introduction of Boc or tert-butyl groups on lactams or acids in the pyroglutamic series have been revisited in a green perspective. Particularly, reaction conditions allowing a quantitative yield in substitution of bromine in tert-butyl bromide were discovered for the first time, allowing the synthesis of tert-butyl pyroglutamate 4. This synthesis of tert-butyl ester by nucleophilic substitution, realized without using concentrated perchloric or sulfuric acid, could be of interest for acid sensitive compounds. On the other hand, we demonstrated that non toxic N-methylimidazole and tert-butanol can pleasantly replace the problematic toxic 4-dimethylaminopyridine (DMAP) and dichloromethane utilized for the N-carbamoylation of lactam 4. This environmentally improved route to compound 4 allowed the development of a multi-gram supply of protected N-aminoethyl and N-hydroxyethyl γ-glutamine 1 and 2.

Crotonase catalysis enables flexible production of functionalized prolines and carbapenams

The biocatalytic versatility of wildtype and engineered carboxymethylproline synthases (CMPSs) is demonstrated by the preparation of functionalized 5-carboxymethylproline derivatives methylated at C-2, C-3, C-4, or C-5 of the proline ring from appropriately substituted amino acid aldehydes and malonyl-coenzyme A. Notably, compounds with a quaternary center (at C-2 or C-5) were prepared in a stereoselective fashion by engineered CMPSs. The substituted-5-carboxymethyl-prolines were converted into the corresponding bicyclic β-lactams using a carbapenam synthetase. The results demonstrate the utility of the crotonase superfamily enzymes for stereoselective biocatalysis, the amenability of carbapenem biosynthesis pathways to engineering for the production of new bicyclic β-lactam derivatives, and the potential of engineered biocatalysts for the production of quaternary centers.