Journal of the Chemical Society. Perkin transactions I p. 2065 - 2069 (1981)
Update date:2022-08-04
Topics:
Smith, Kevin M.
Milgrom, Lionel R.
Kenner, George W.
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.
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Doi:10.1016/0022-328X(84)80608-7
(1984)Doi:10.1021/jo00078a016
(1993)Doi:10.1021/jm00344a011
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(1982)Doi:10.1007/BF00963416
()Doi:10.1016/S0040-4039(01)90528-3
(1981)
