151012-08-7

Basic information

• Product Name: N^α,N^δ,N^ω-tris(benzyloxycarbonyl)-L-arginyl-N-methyl-L-norleucyl-L-aspartic acid β-cyclohexyl ester
• Synonyms: N^α,N^δ,N^ω-tris(benzyloxycarbonyl)-L-arginyl-N-methyl-L-norleucyl-L-aspartic acid β-cyclohexyl ester
• CAS NO: 151012-08-7
• Molecular Weight: 901.026
• Mol File: 151012-08-7.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: N^α,N^δ,N^ω-tris(benzyloxycarbonyl)-L-arginyl-N-methyl-L-norleucyl-L-aspartic acid β-cyclohexyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: N^α,N^δ,N^ω-tris(benzyloxycarbonyl)-L-arginyl-N-methyl-L-norleucyl-L-aspartic acid β-cyclohexyl ester(151012-08-7)
• EPA Substance Registry System: N^α,N^δ,N^ω-tris(benzyloxycarbonyl)-L-arginyl-N-methyl-L-norleucyl-L-aspartic acid β-cyclohexyl ester(151012-08-7)

Safety Data

• Hazardous Substances Data: 151012-08-7(Hazardous Substances Data)

Upstream product

• 151012-05-4 tris(benzyloxycarbonyl)-L-arginyl-N-methylnorleucine tert-butyl ester 
• 151012-06-5 N^α,N^δ,N^ω-tris(benzyloxycarbonyl)-L-arginyl-N-methylnorleucine 
• 191930-81-1 N-methylnorleucine tert-butyl ester 
• 117903-25-0 N-BOC-N-methylnorleucine 
• 14611-34-8 N^α,N^δ,N^ω-tris(benzyloxycarbonyl)-L-arginine 
• 151012-07-6 N^α,N^δ,N^ω-tris(benzyloxycarbonyl)-L-arginyl-N-methyl-L-norleucyl-L-aspartic acid β-cyclohexyl-α-tert-butyl ester 

Relevant articles and documents

Stabilized analogs of thymopentin. 1. 4,5-Ketomethylene pseudopeptides

The pentapeptide, thymopentin (Arg1-Lys2-Asp3-Val4-Tyr5) is known for its activity as an immunomodulating drug, but with limited half-life in plasma. In this first paper of a series of three studies, the synthesis of analogs stabilized at the peptide bond between the C-terminal amino acids via insertion of a ketomethylene moiety is described. N-Blocked pseudopeptides containing Val(k)Phe, Ala(k)Phe, and Val(k)Val units were prepared and attached to chloromethyl Merrifield resin via the carboxy terminal. Removal of the N-BOC group by trifluoroacetic acid was followed by sequential coupling with N-BOC dipeptides of aspartic acid to yield resin-bound N-BOC pseudotetrapeptides. Removal of N-BOC and coupling with N-BOC-r-N- tosylarginine followed by total cleavage of blocking groups and resin by HF afforded the target pseudopentapeptides. The analogs were found to compete favorably with thymopentin for binding to CEM cells, but binding was reduced by about 20-30% on average. All analogs showed significant enhancement of half-life versus thymopentin in mouse serum, but most showed only modest improvement in human serum. Insertion of proline or norleucine at position 2 in the chain caused a substantial increase in half-life (3-4-fold), while N- methylnorleucine conferred complete stability in the analogs.