1385775-57-4

Basic information

• Product Name: N-Fmoc-L-Cys(S-(4-OMe-Bz))-OH
• Synonyms: N-Fmoc-L-Cys(S-(4-OMe-Bz))-OH
• CAS NO: 1385775-57-4
• Molecular Weight: 477.538
• Mol File: 1385775-57-4.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: N-Fmoc-L-Cys(S-(4-OMe-Bz))-OH(CAS DataBase Reference)
• NIST Chemistry Reference: N-Fmoc-L-Cys(S-(4-OMe-Bz))-OH(1385775-57-4)
• EPA Substance Registry System: N-Fmoc-L-Cys(S-(4-OMe-Bz))-OH(1385775-57-4)

Safety Data

• Hazardous Substances Data: 1385775-57-4(Hazardous Substances Data)

Upstream product

• 135248-89-4 N^α-fluoren-9-ylmethoxycarbonyl-L-cysteine 
• 4231-69-0 1-(4-methoxybenzoyl)-1H-1,2,3-benzotriazole 
• 28920-43-6 (fluorenylmethoxy)carbonyl chloride 
• 1131148-55-4 1-[(9-fluorenylmethyloxycarbonyl)]benzotriazole 

Relevant articles and documents

Cysteinoyl- and Cysteine-containing Dipeptidoylbenzotriazoles with Free Sulfhydryl Groups: Easy Access to N-terminal and Internal Cysteine Peptides

N-Protected cysteines 4a-c each with a free sulfhydryl group were prepared in 70-75% yields by treatment of l-cysteine with 1-(benzyloxycarbonyl) benzotriazole (Cbz-Bt) 1a, N-(tert-butyloxy-carbonyl)benzotriazole (Boc-Bt) 1b, and 1-(9-fluorenylmethoxy-carbonyl)benzotriazole (Fmoc-Bt) 1c, respectively. N-Protected, free sulfhydryl cysteines 4a-c were then converted into the corresponding N-protected, free sulfhydryl cysteinoylbenzotriazoles 7a-c (70-85%), which on treatment with diverse amino acids and dipeptides afforded the corresponding N-protected, free sulfhydryl N-terminal cysteine dipeptides 8a-e and tripeptides 8f-h in 73-80% yields. N-Protected, free sulfhydryl cysteine-containing dipeptides 9a,b were converted into the corresponding N-protected, free sulfhydryl dipeptidoylbenzotriazoles 10a,b (69-81%), which on treatment with amino acids, dipeptides, and a tripeptide afforded internal cysteine tripeptides 11a-c, tetrapeptides 11d,e and pentapeptide 11f, each containing a N-protected, free sulfhydryl groups in 70-90% yields under mild conditions. Treatment of N-protected, free sulfhydryl cysteinoylbenzotriazole 7a with diamines 12a,b afforded directly the cysteine-containing disulfide-bridged cyclic peptides 14a,b in 50% yields. Novel and stable N-protected, free sulfhydryl, cysteine-containing dipeptidoylbenzotriazoles formed internal cysteine containing N-protected free sulfhydryl tripeptides, tetrapeptides, and pentapeptide under mild reaction conditions in good yields that can be useful in the syntheses of other naturally occurring or biologically active cysteine-containing peptides.