Synthesis of a neamine dimer targeting the dimerization initiation site of HIV-1 RNA.
A neamine dimer designed to bind to a specific sequence of HIV-1 RNA has been synthesized. Starting from neomycin B (1), a five-step synthesis efficiently provided a key protected neamine monomer 6 (28%). From the latter, coupling reactions with activated diacids gave dimers. After deprotection, a neamine dimer was obtained as the hexachlorohydrate salt 15 with 13% overall yield over nine steps.
Bodlenner
Anne
A
Laboratoire de synthèse et réactivité organique, Institut de Chimie, Université Louis Pasteur, 4 rue Blaise Pascal, 67070 Strasbourg, France.
Alix
Aurélien
A
Weibel
Jean-Marc
JM
Pale
Patrick
P
Ennifar
Eric
E
Paillart
Jean-Christophe
JC
Walter
Philippe
P
Marquet
Roland
R
Dumas
Philippe
P
D000617:Aminoglycosides / Q000737:chemistry* / Q000494:pharmacology; D019380:Anti-HIV Agents / Q000138:chemical synthesis*; D019281:Dimerization; D005601:Framycetin / Q000737:chemistry* / Q000494:pharmacology; D015497:HIV-1 / Q000235:genetics*; D015394:Molecular Structure; D009690:Nucleic Acid Conformation; D012367:RNA, Viral / Q000737:chemistry* / Q000235:genetics*; D024363:Transcription Initiation Site
D000617:Aminoglycosides; D019380:Anti-HIV Agents; D012367:RNA, Viral; D005601:Framycetin; C488396:neamine