Synthesis of a bis-azido analogue of acromelic acid for radioisotope-free photoaffinity labeling and biochemical studies

Pi Sun; Guang Xing Wang; Kyoji Furuta; Masaaki Suzuki

doi:10.1016/j.bmcl.2006.01.083

Synthesis of a bis-azido analogue of acromelic acid for radioisotope-free photoaffinity labeling and biochemical studies

Bioorg Med Chem Lett. 2006 May 1;16(9):2433-6. doi: 10.1016/j.bmcl.2006.01.083. Epub 2006 Feb 15.

Authors

Pi Sun¹, Guang Xing Wang, Kyoji Furuta, Masaaki Suzuki

Affiliation

¹ Regeneration and Advanced Medical Science, Graduate School of Medicine, Gifu University, Gifu 501-1193, Japan.

PMID: 16480870
DOI: 10.1016/j.bmcl.2006.01.083

Abstract

A novel acromelic acid analogue containing a phenyl group possessing two different types of azido functional groups, of which one is the aromatic N3 acting as a photoaffinity group to bind to a target protein by photoirradiation and the other is alkyl N3 group which survives photolysis acting as a detecting group through the Staudinger-Bertozzi reaction to identify the ligated product, was designed and synthesized as a radioisotope-free biochemical probe potentially for studies on kainoid receptors.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Azides / chemistry*
Drug Design
Kainic Acid / analogs & derivatives*
Kainic Acid / chemical synthesis
Kainic Acid / chemistry
Kainic Acid / pharmacology
Molecular Conformation
Photoaffinity Labels / chemical synthesis*
Photoaffinity Labels / chemistry
Photoaffinity Labels / pharmacology*
Proteins / chemistry
Proteins / drug effects
Receptors, Kainic Acid / chemistry
Receptors, Kainic Acid / drug effects
Stereoisomerism
Structure-Activity Relationship

Substances

Azides
Photoaffinity Labels
Proteins
Receptors, Kainic Acid
acromelic acid A
Kainic Acid