PMID: 2504922Sep 1, 1989Paper

Synthesis and biological activity of photoactive derivatives of erythromycin

Journal of Medicinal Chemistry
M A ArévaloJ P Ballesta

Abstract

Five photoactive derivatives of erythromycin have been synthesized by linking to 9(S)-aminoerythromycin either an aryl azide or a p-nitrophenyl ether. One derivative is an amide formed by reaction with (5-azido-2-formyl-phenoxy)acetic acid. Three derivatives are also amides, synthesized with 4-(p-nitroguaiacoxy)butanoic acid as a photoreactive group either directly or by interposing an amino acid (glycine or tyrosine). The last derivative is the product of the aldehyde condensation of aminoerythromycin with 10-(p-nitroguaiacoxy)decanal. Two of these derivatives can easily be made radioactive for affinity labeling studies either by reduction with [3H]borohydride (aryl azide derivative) or by 125I iodination (4-(p-nitroguaiacoxy)tyrosyl derivative). Although affected to different extents, the five erythromycin derivatives are biologically active and bind to the erythromycin-specific site on the bacterial ribosomes. In addition, the introduction of these groups changes the erythromycin inhibition pattern of peptide bond model reactions.

Citations

Jul 25, 1998·The Journal of Biological Chemistry·I K WowerR A Zimmermann
Nov 1, 1995·Biochemistry and Cell Biology = Biochimie Et Biologie Cellulaire·B T PorseR A Garrett
Apr 12, 2003·The Journal of Biological Chemistry·Jerry R ColcaAlexander S Mankin

❮ Previous
Next ❯

Related Concepts

Related Feeds

Aminoglycosides

Aminoglycoside is a medicinal and bacteriologic category of traditional Gram-negative antibacterial medications that inhibit protein synthesis and contain as a portion of the molecule an amino-modified glycoside. Discover the latest research on aminoglycoside here.

Aminoglycosides (ASM)

Aminoglycoside is a medicinal and bacteriologic category of traditional Gram-negative antibacterial medications that inhibit protein synthesis and contain as a portion of the molecule an amino-modified glycoside. Discover the latest research on aminoglycoside here.