TY - JOUR
T1 - Synthesis of porphyrin α,ω-bis(methylamino)peptide constructs
AU - Matthews, Susan E.
AU - Pouton, Colin W.
AU - Threadgill, Michael D.
PY - 1999/1/1
Y1 - 1999/1/1
N2 - New monofunctionalised electrophilic and nucleophilic derivatives of 5,10,15,20-tetraphenyl-21H,23H-porphine (TPP) have been developed for controlled attachment to peptide amino and carboxyl side-chains, respectively. Reaction of 5-(4-aminophenyl)-10,15,20-triphenyl-21H,23H- porphine with 4-nitrophenyl chloroformate gave the corresponding nitrophenyl carbamate which coupled efficiently to lysine ε-amines. The aminophenylporphyrin, a poor nucleophile, was converted to a primary aliphatic amine by coupling with glycine. This glycylaminophenylporphyrin reacted readily with acyl azides derived from extended Glu side-chains. These systems offer access to novel polymeric porphinatomanganese(III) agents for contrast enhancement in MRI.
AB - New monofunctionalised electrophilic and nucleophilic derivatives of 5,10,15,20-tetraphenyl-21H,23H-porphine (TPP) have been developed for controlled attachment to peptide amino and carboxyl side-chains, respectively. Reaction of 5-(4-aminophenyl)-10,15,20-triphenyl-21H,23H- porphine with 4-nitrophenyl chloroformate gave the corresponding nitrophenyl carbamate which coupled efficiently to lysine ε-amines. The aminophenylporphyrin, a poor nucleophile, was converted to a primary aliphatic amine by coupling with glycine. This glycylaminophenylporphyrin reacted readily with acyl azides derived from extended Glu side-chains. These systems offer access to novel polymeric porphinatomanganese(III) agents for contrast enhancement in MRI.
UR - http://www.scopus.com/inward/record.url?scp=0032725041&partnerID=8YFLogxK
U2 - 10.1039/a906044h
DO - 10.1039/a906044h
M3 - Article
AN - SCOPUS:0032725041
VL - 23
SP - 1087
EP - 1096
JO - New Journal of Chemistry
JF - New Journal of Chemistry
SN - 1144-0546
IS - 11
ER -