Caged chemotactic peptides.
This work has as its ultimate goal the creation of a concentration spike of a chemoattractant peptide in a time-resolved and spatially defined way using a light pulse. This strategy requires "caging" the peptide with a photochemically removable group. Model studies used alanine ethyl ester in reductive amination with nitrobenzaldehydes to form two different N-nitrobenzyl derivatives. An fMLF peptide bearing these two N-terminal nitrobenzyl groups was also prepared. The yield and kinetics of their deprotection to return the fMLF peptide were determined. It was established that the caged peptides have vastly reduced biological activity as chemoattractants, as designed.
Pirrung
M C
MC
Department of Pathology, School of Dental Medicine, University of Pennsylvania, Philadelphia, Pennsylvania 19104, USA.
Drabik
S J
SJ
Ahamed
J
J
Ali
H
H
D000818:Animals; D002634:Chemotaxis, Leukocyte; D008322:Mammals; D009240:N-Formylmethionine Leucyl-Phenylalanine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D009842:Oligopeptides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D010777:Photochemistry; D044042:Receptors, Formyl Peptide; D011971:Receptors, Immunologic / Q000187:drug effects / Q000502:physiology*; D018000:Receptors, Peptide / Q000187:drug effects / Q000502:physiology*; D014407:Tumor Cells, Cultured; D001619:beta-N-Acetylhexosaminidases / Q000378:metabolism
D009842:Oligopeptides; D044042:Receptors, Formyl Peptide; D011971:Receptors, Immunologic; D018000:Receptors, Peptide; D009240:N-Formylmethionine Leucyl-Phenylalanine; D001619:beta-N-Acetylhexosaminidases