Caged chemotactic peptides.

M C Pirrung; S J Drabik; J Ahamed; H Ali

doi:10.1021/bc000001g

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Caged chemotactic peptides.

M C Pirrung·S J Drabik·J Ahamed·H Ali

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Abstract

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.

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Animals Chemotaxis, Leukocyte Mammals N-Formylmethionine Leucyl-Phenylalanine Oligopeptides Photochemistry Receptors, Formyl Peptide Receptors, Immunologic Receptors, Peptide Tumor Cells, Cultured beta-N-Acetylhexosaminidases Journal Article Research Support, U.S. Gov't, P.H.S.

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M C Pirrung, S J Drabik, J Ahamed, H Ali. Caged chemotactic peptides.. https://doi.org/10.1021/bc000001g

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