Synthesis of (+),(-)-neamine and their positional isomers as potential antibiotics

Do Hyun Ryu; Choon-Hong Tan; Robert R Rando

doi:10.1016/s0960-894x(02)01073-9

Synthesis of (+),(-)-neamine and their positional isomers as potential antibiotics

Bioorg Med Chem Lett. 2003 Mar 10;13(5):901-3. doi: 10.1016/s0960-894x(02)01073-9.

Authors

Do Hyun Ryu¹, Choon-Hong Tan, Robert R Rando

Affiliation

¹ Department of Biological Chemistry and Molecular Pharmacology, Harvard Medical School, 45 Shattuck Street, Boston, MA 02115, USA.

PMID: 12617917
DOI: 10.1016/s0960-894x(02)01073-9

Abstract

The syntheses of (+)-neamine 1, (-)-neamine ent-1 and their positional isomers 2, 3, ent-2 and ent-3 are reported as potential new scaffolds for novel aminoglycoside antibiotics. These isomers exhibit similar inhibitory activities, as shown using an in vitro translation assay. A simple model is proposed to explain this lack of stereospecific binding to the ribosomal RNA.

Publication types

Research Support, U.S. Gov't, P.H.S.

MeSH terms

Anti-Bacterial Agents / chemical synthesis*
Anti-Bacterial Agents / chemistry
Anti-Bacterial Agents / pharmacology*
Binding Sites
Isomerism
Neomycin / chemical synthesis*
Neomycin / chemistry
Neomycin / pharmacology*
Protein Biosynthesis / drug effects
RNA, Ribosomal / antagonists & inhibitors
RNA, Ribosomal / metabolism*

Substances

Anti-Bacterial Agents
RNA, Ribosomal
Neomycin

Grants and funding

EY-12375/EY/NEI NIH HHS/United States