79900-16-6Relevant academic research and scientific papers
Syntheses of Monofunctional Porphyrinyl Peptides containing Glycine and Leucine
Smith, Kevin M.,Milgrom, Lionel R.,Kenner, George W.
, p. 2065 - 2069 (1981)
4,6,8-Triethyl-2-(2-methoxycarbonylethyl)-1,3,5,7-tetramethylporphyrin is synthesised using the a,c-biladiene route.Activated derivatives of the corresponding porphyrin free carboxylic acid were coupled with glycine ethyl ester, and the resulting porphyrinyl-glycine ester was hydrolysed and coupled with L-leucine methyl ester to give a porphyrinyl dipeptide; an isomer of this dipeptide was prepared by direct coupling of the activated porphyrin with L-leucyl-glycine methyl ester.A porphyrinyl tripeptide was also prepared in low yield by coupling the porphyrinyl-glycine with L-leucyl-glycine methyl ester.Attempts to synthesise porphyrinyl peptides containing unprotected histidine (which would have yielded haem protein models) were largely unsuccessful.Mass-spectral fragmentation patterns for the synthetic porphyrinyl peptides are reported.
