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FEBS Lett. 2002 Aug 14;525(1-3):20-4.

A caged sperm-activating peptide that has a photocleavable protecting group on the backbone amide.

Author information

1
National Institute of Advanced Industrial Science and Technology, Midorigaoka, 563-8577, Ikeda, Japan.

Abstract

A backbone-caged sperm-activating peptide (caged speract) that has a 2-nitrobenzyl group at a backbone amide and a vastly reduced affinity for its receptor (IC50=950 nM) was synthesized. UV irradiation of caged speract photocleaves the 2-nitrobenzyl group (tau1/2=26 micros), restoring its affinity (IC50=0.67 nM) and ability to increase sperm intracellular pH and Ca2+, as intact speract. Backbone caging of the biological activity was more efficient than side chain caging, which adds a nitrobenzyl group on the peptide side chain. The backbone caging strategy described can be used as a general procedure to cage biologically active peptides, which have no side chain for introduction of a caging group.

PMID:
12163154
DOI:
10.1016/s0014-5793(02)03000-4
[Indexed for MEDLINE]
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