620567-53-5

Basic information

• Product Name: N-α-(fluorenylmethoxy)carbonyl-D-valyl-(S-triphenylmethyl)-D-cysteinyl-(O-t-butyldimethylsilyl)-L-threonine methyl ester
• Synonyms: N-α-(fluorenylmethoxy)carbonyl-D-valyl-(S-triphenylmethyl)-D-cysteinyl-(O-t-butyldimethylsilyl)-L-threonine methyl ester
• CAS NO: 620567-53-5
• Molecular Weight: 914.251
• Mol File: 620567-53-5.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: N-α-(fluorenylmethoxy)carbonyl-D-valyl-(S-triphenylmethyl)-D-cysteinyl-(O-t-butyldimethylsilyl)-L-threonine methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: N-α-(fluorenylmethoxy)carbonyl-D-valyl-(S-triphenylmethyl)-D-cysteinyl-(O-t-butyldimethylsilyl)-L-threonine methyl ester(620567-53-5)
• EPA Substance Registry System: N-α-(fluorenylmethoxy)carbonyl-D-valyl-(S-triphenylmethyl)-D-cysteinyl-(O-t-butyldimethylsilyl)-L-threonine methyl ester(620567-53-5)

Safety Data

• Hazardous Substances Data: 620567-53-5(Hazardous Substances Data)

Upstream product

• 167015-11-4 Fmoc-D-Cys(Trt)-OH 
• 620567-49-9 N-α-(fluorenylmethoxy)carbonyl-(S-triphenylmethyl)-D-cysteinyl-(O-t-butyldimethylsilyl)-L-threonine methyl ester 
• 3373-59-9 L-threonine methyl ester 
• 84624-17-9 N-(9-fluorenylmethoxycarbonyl)-D-valine 

Downstream Products

• 620567-97-7 methyl (7R,11R,14R,17S,20S,E)-20-[(R)-1-(tert-butyldimethylsiloxy)ethyl]-7-hydroxy-11,14-diisopropyl-9,12,15,18-tetraoxo-1,1,1-triphenyl-17-tritylthiomethyl-2-thia-10,13,16,19-tetraazahenicos-5-en-21-oate 
• 620567-24-0 (7R,11R,14R,17S,20S,E)-20-[(R)-1-(tert-butyldimethylsiloxy)ethyl]-7-hydroxy-11,14-diisopropyl-9,12,15,18-tetraoxo-1,1,1-triphenyl-17-tritylthiomethyl-2-thia-10,13,16,19-tetraazahenicos-5-en-21-oic acid 
• 620568-02-7 (3S,6S,9R,12R,16S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-9,12-diisopropyl-16-((E)-4-tritylsulfanyl-but-1-enyl)-6-tritylsulfanylmethyl-1-oxa-4,7,10,13-tetraaza-cyclohexadecane-2,5,8,11,14-pentaone 
• 620567-59-1 N-α-(fluorenylmethoxy)carbonyl-D-valyl-D-valyl-(S-triphenylmethyl)-D-cysteinyl-(O-t-butyldimethylsilyl)-L-threonine methyl ester 
• 620567-30-8 D-valyl-D-valyl-(S-triphenylmethyl)-D-cysteinyl-(O-t-butyldimethylsilyl)-L-threonine methyl ester 

Relevant articles and documents

Total Synthesis of the Depsipeptide FR901375 and Preliminary Evaluation of Its Biological Activity

The bicyclic depsipeptide FR901375 was efficiently synthesized in a highly convergent manner. The synthesis involved the condensation of a d-valine–d-valine–d-cysteine-containing segment with a (3S,4E)-3-hydroxy-7-mercapto-4-heptenoic acid–l-threonine-containing segment to directly assemble the corresponding seco-amino acid, followed by cyclization to construct the desired 16-membered macrocyclic ring. The potency of the synthesized FR901375 was determined in assays for histone deacetylase (HDAC) inhibition and cell-growth inhibition, and the results were compared to those obtained for the clinically approved depsipeptide FK228 (romidepsin). It was found that FR901375 shows extremely high selectivity (957-fold) for a class I HDAC 1 (GI50= 1.7 nm) over a class II HDAC 6 (GI50= 1627 nm), and shows cell-growth inhibition GI50values in the low nanomolar region. Furthermore, new aspects of the structure–activity relationship of bicyclic depsipeptide HDAC inhibitors were revealed.