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

FEBS Letters

Darszon, Alberto²  Yumoto, Noboru¹  Tatsu, Yoshiro¹  Nishigaki, Takuya² 

[1] National Institute of Advanced Industrial Science and Technology (AIST), Midorigaoka, Ikeda 563-8577, Japan;Departamento Genética y Fisiologı́a Molecular, Instituto de Biotecnologı́a, Universidad Nacional Autónoma de México (UNAM), Cuernavaca, Morelos 62250, Mexico

关键词: Caged peptide;    Speract;    Backbone amide;    Sperm;   

DOI  :  10.1016/S0014-5793(02)03000-4

学科分类：生物化学/生物物理

来源: John Wiley & Sons Ltd.

【 摘 要 】

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 (τ _1/2=26 μs), 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.

【 授权许可】

Unknown