3-N,N-Dimethylamino-3-deoxy lincomycin: a structure-based hybrid between lincomycin and the desosamine unit of erythromycin.
The observation that the desosamine sugar unit in erythromycin and the methyl thiolincosaminide portion of lincomycin occupy virtually identical sites on the 23S rRNA according to X-ray crystallograpaic data, instigated the synthesis of 3-N,N-dimethylamino-3-deoxy lincomycin as a hybrid structure. The synthesis in eight steps from lincomycin, involving a trans-diequatorial opening of an intermediate epoxide as the key step, is described.
Hanessian
Stephen
S
PO Box 6128, Department of Chemistry, University of Montreal, Montreal, QC, Canada H3C 3J7. stephen.hanessian@umontreal.ca
Kothakonda
Kiran Kumar
KK
D018360:Crystallography, X-Ray; D004917:Erythromycin / Q000737:chemistry*; D008034:Lincomycin / Q000031:analogs & derivatives* / Q000737:chemistry*; D055231:Lincosamides; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D012338:RNA, Ribosomal, 23S / Q000737:chemistry; D013055:Spectrophotometry, Infrared
C505670:3-N,N-dimethylamino-3-deoxy lincomycin; D055231:Lincosamides; D012338:RNA, Ribosomal, 23S; D004917:Erythromycin; D008034:Lincomycin