103818-50-4Relevant academic research and scientific papers
C-terminal Sequencing of Peptides: An Investigation of the Iminohydantoin Method
Bentley, John D.,Maclaren, John A.
, p. 537 - 542 (2007/10/02)
A method for the C-terminal sequencing of peptides was briefly outlined at a conference in 1975, but no further results have been reported since.This method converts the carboxy group into an acyl-S-alkylisothioureide, which on treatment with base reportedly gives the acylcyanamide.Following cyclization and hydrolysis, the iminohydantoin corresponding to the C-terminal residue is formed.Thus the peptide chain is shortened by one residue at each cycle.Using model peptides, we have prepared authentic samples of the supposed products at each step, and have shown thatthe acylcyanamide is not an intermediate in this reaction.With glycine as the C-terminal residue, the iminohydantoin is obtained in near-quantitative yield.
Acyl, N-Protected α-Aminoacyl, and Peptidyl Derivatives as Prodrug Forms of the Alcohol Deterrent Agent Cyanamide
Kwon, Chul-Hoon,Nagasawa, Herbert T.,DeMaster, Eugene G.,Shirota, Frances N.
, p. 1922 - 1929 (2007/10/02)
Cyanamide , a potent aldehyde dehydrogenase (AlDH) inhibitor that is used therapeutically as an alcohol deterrent agent, is known to be rapidly metabolized and excreted in the urine as acetylcyanamide (1). On the basis of our observation that 1 is deacetylated to cyanamide in vivo, albeit very slightly, thereby serving as a precursor or prodrug form of the latter, several acyl derivatives of cyanamide were synthesized specifically as prodrugs, including benzoylcyanamide (2), pivaloylcyanamide (3), and 1-adamantoylcyanamide (4), as well as long- and medium-chain fatty acyl derivatives such as palmitoyl- (6), stearoyl- (7), and n-butyrylcyanamide (5). N-Protected α-aminoacyl and peptidyl derivatives of cyanamide were also synthesized, and these include N-carbobenzoxyglycyl- (10), hippuryl- (13), N-benzoyl-L-leucyl- (14), N-carbobenzoxyglycyl-L-leucyl- (18), N-carbobenzoxy-L-pyroglutamyl- (22), L-pyroglutamyl-L-leucyl- (19), and L-pyroglutamyl-L-phenylalanylcyanamide (20). All of these prodrugs of cyanamide raised ethanol-derived blood acetaldehyde levels in rats significantly over controls 3h after ip drug administration, and some of these were still capable of elevating blood acetaldehyde 16 h post drug administration. A selected group of cyanamide prodrugs were also evaluated by the oral route of administration and showed nearly equivalent activity as the ip route in elevating ethanol-derived blood acetaldehyde. These results suggest potential utility of these prodrugs as deterrent agents for the treatment of alcoholism.
