154226-60-5

Usage

Uses

Used in Research Applications:
Clasto-Lactacystin Beta-Lactone is used as a proteasomal inhibitor for studying the role of the proteasome in various cellular processes, including protein degradation, cell cycle regulation, and signal transduction pathways.
Used in Pharmaceutical Industry:
Clasto-Lactacystin Beta-Lactone is used as a 20S proteasome and cathepsin A inhibitor for the development of therapeutic agents targeting cancer and other diseases associated with the dysregulation of the proteasome.
Used in Cancer Research:
Clasto-Lactacystin Beta-Lactone is used as a tool to investigate the role of the proteasome in cancer cell survival and proliferation, as well as to identify potential therapeutic targets for cancer treatment.
Used in Drug Delivery Systems:
Clasto-Lactacystin Beta-Lactone can be incorporated into drug delivery systems to improve its bioavailability, targeting, and therapeutic efficacy in various applications, including cancer treatment and other proteasome-related diseases.

Biological Activity

cell-permeable. a highly specific, potent and irreversible proteasome inhibitor. lactacystin (cat. no. 1709-200) acts as a precursor for clasto-lactacystin β-lactone and the latter compound is at least 10 times more active than the parent lactacystin

Biochem/physiol Actions

Clasto-Lactacystin β-lactone (cLβL) is synthesized from lactacystin. It is cell-permeable and cLβL acts on the N-terminal threonine of subunit proteasome β -subunit X It also inhibits 20S proteasome activity in Haloferax volcanii?by acting in the N-threonine residue of the? β -type subunits.

Upstream product

• 145451-97-4 (3R,4S,5R,1'S)-4-hydroxy-5-(1'-hydroxy-2'-methylpropyl)-3-methylpyrrolidin-2-one-5-carboxylic acid 
• 212772-65-1 (1R,4R,5S)-1-((S)-1-Hydroxy-2-methyl-propyl)-2-(4-methoxy-benzyl)-4-methyl-6-oxa-2-aza-bicyclo[3.2.0]heptane-3,7-dione 
• 167773-32-2 (2R,3R,4R,1'S)-(+)-3-hydroxy-2-(1-hydroxy-2-methyl-propyl)-4-methyl-5-oxo-pyrrolidine-2-carboxylic acid methyl ester 
• 878011-75-7 ethyl (1S)-1-[(tert-butoxycarbonyl)amino]-2-isopropylcyclopent-2-ene-1-carboxylate 
• 20515-15-5 methyl (2E)-4-methylpent-2-enoate 
• 148843-19-0 (4R,5S)-4-Formyl-5-isopropyl-2-phenyl-4,5-dihydro-oxazole-4-carboxylic acid methyl ester 
• 148843-18-9 (4S,5S)-4-Hydroxymethyl-5-isopropyl-2-phenyl-4,5-dihydro-oxazole-4-carboxylic acid methyl ester 
• 148843-21-4 (4S,5S)-4-((1S,2R)-2-Carboxy-1-hydroxy-propyl)-5-isopropyl-2-phenyl-4,5-dihydro-oxazole-4-carboxylic acid methyl ester 
• 227946-97-6 (2R,3S)-(para-bromophenyl)-2-benzylcarbamate-3-hydroxy-4-methylpentanoate 
• 145484-22-6 (4R,5S)-3-Benzyl-4-(tert-butyl-dimethyl-silanyloxymethyl)-5-isopropyl-oxazolidine-4-carbaldehyde 
• 1334590-08-7 (2R,3S)-1-tert-butyl 2-methyl 2-((S)-1-acetoxy-2-methylpropyl)-3-(tert-butyldimethylsilyloxy)-5-oxopyrrolidine-1,2-dicarboxylate 
• 1334589-99-9 (2R,3S)-methyl 3-(tert-butyldimethylsilyloxy)-2-((tert-butyl-dimethylsilyloxy)methyl)-5-oxopyrrolidine-2-carboxylate 
• 1334590-00-9 (2R,3S)-methyl 3-(tert-butyldimethylsilyloxy)-2-((tert-butyldimethylsilyloxy)methyl)-1-(4-methoxybenzyl)-5-oxopyrrolidine-2-carboxylate 
• 1334590-01-0 (2R,3S)-methyl 3-(tert-butyldimethylsilyloxy)-2-(hydroxy-methyl)-1-(4-methoxybenzyl)-5-oxopyrrolidine-2-carboxylate 

Downstream Products

• 133343-34-7 Lactacystin 
• 155975-72-7 (1R,4R,5S)-1-((R)-1-Hydroxy-2-methyl-propyl)-4-methyl-6-oxa-2-aza-bicyclo[3.2.0]heptane-3,7-dione 

Relevant academic research and scientific papers

Total Synthesis of Proteasome Inhibitor (-)-Omuralide through Asymmetric Ketene [2 + 2]-Cycloaddition

The total synthesis of (-)-omuralide, a potent specific proteasome inhibitor, has been achieved through an unprecedented route. The C3 and C4 chiral centers of the natural product have been selectively installed by an asymmetric [2 + 2]-cycloaddition betw

Application of Two Direct C(sp3)-H Functionalizations for Total Synthesis of (+)-Lactacystin

(Figure Presented). Herein, we report a new synthetic route from (S)-pyroglutaminol to (+)-lactacystin, a potent inhibitor of the 20S proteasome. The photoinduced intermolecular C(sp3)-H alkynylation and intramolecular C(sp3)-H acylation chemo- and stereoselectively constructed the tetra- and trisubstituted carbon centers, respectively. The obtained bicycle was transformed into the target compound in a concise manner. The present total synthesis demonstrates the power of the direct C(sp3)-H functionalizations for the assembly of multiple functionalized structures of natural products.

Stereospecific total syntheses of proteasome inhibitors omuralide and lactacystin

Omuralide, a transformation product of the microbial metabolite lactacystin, was the first molecule discovered as a specific inhibitor of the proteasome and is unique in that it specifically inhibits the proteolytic activity of the 20S subunit of the prot

Enantioselective total syntheses of omuralide, 7-epi-omuralide, and (+)-lactacystin

(Chemical Equation Presented) An alkylidene carbene 1,5-CH insertion has been used as a key step in an enantioselective total syntheses of omuralide, its C7-epimer, and (+)-lactacystin. An additional noteworthy feature of the synthesis is the use of a nov

Stereogenic evolution of clasto-lactacystin β-lactone from L-serine

Reported herein is a novel synthesis of clasto-lactacystin β-lactone. The γ-lactam core was selectively prepared by an intramolecular C-H insertion to establish the stereocenter, C(6). The ensuing construction of the quaternary C(5) and carbinol C(9) cent

SUBSTITUTED 2-PYRROLIDONE DERIVATIVES AS FUNGICIDES AND INSECTICIDES

The use of a compound of formula (I) or a salt thereof, where the symbols have the meanings given in the description, for the control of phytopathogenic mircroorganisms of harmful animals.

Catalytic asymmetric total synthesis of (+)-lactacystin

Total synthesis of (+)-lactacystin, a potent and selective proteasome inhibitor, was accomplished using a catalytic enantioselective Strecker reaction of a ketoimine as the initial key step. An enone-derived N-phosphinoyl ketoimine 7 was selected as a sta

Enantioselective total syntheses of (-)-clasto-lactacystin β-lactone and 7-epi-(-)-clasto-lactacystin β-lactone

An alkylidene carbene 1,5-CH insertion has been used as a key step in an efficient enantioselective total synthesis of (-)-clasto-lactacystin β-lactone, and its C7-epimer. An additional noteworthy feature of the synthesis is the use of a novel oxidative deprotection procedure, utilizing DMDO, for the conversion of a late-stage benzylidene acetal into a primary alcohol and a secondary benzoate ester. The Royal Society of Chemistry 2006.

A concise route to (+)-lactacystin

A facile chromatography-free route to Kang's intermediate for the synthesis of (+)-lactacystin, a potent proteasome inhibitor, has been developed starting with Brown's asymmetric crotylation of tert-butyl 5-formyl-2,2-dimethyl-1,3- dioxan-5-ylcarbamate, e

Total synthesis of (+)-lactacystin

A double stereodifferentiating crotylation between aldehyde 1 and silane (S)-2 to afford homoallylic alcohol 3 is the key diastereoselective step (anti:syn > 30:1) in an efficient asymmetric synthesis of (+)-lactacystin. This compound is a metabolite isol