Regioselective synthesis of bifunctional macrolides for probing ribosomal binding.
[structure: see text] Bifunctional macrolides projecting an anchor group to the right or left spatial position of the lactone ring were synthesized. The regioselectivity of the key [3 + 2] cycloaddition process was controlled by the remote cladinose group attached to the C-3 position. These conformationally constrained molecules were employed as molecular probes to study the ribosomal binding sites of bifunctional macrolide antibiotics.
Ma
Zhenkun
Z
Infectious Disease Research, Abbott Laboratories, D47P, AP52, 200 Abbott Park Road, Abbott Park, Illinois 60064, USA. zhenkun.ma@abbott.com
Li
Leping
L
Rupp
Michael
M
Zhang
Suoming
S
Zhang
Xiaolin
X
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D018942:Macrolides; D008826:Microbial Sensitivity Tests; D015335:Molecular Probes; D012270:Ribosomes / Q000378:metabolism*
D000900:Anti-Bacterial Agents; D018942:Macrolides; D015335:Molecular Probes