Synthesis of base-modified dihydropacidamycins.
We describe in this paper the synthesis of 1,2-di-O-acetyl-5-azido-3,5-dideoxy-alpha,beta-L-arabinofuranose, a carbohydrate donor that was used for the synthesis of 1-(5'-amino-3',5'-dideoxy-alpha-L-arabinofuranosyl)uracil, the nucleoside found in dihydropacidamycin D. The carbohydrate donor was also used for the synthesis of a set of new nucleosides that were introduced in new dihydropacidamycins. These compounds were tested for biological activity, and the results showed that uracil is the only base recognized by MraY.
Lemoine
Rémy C
RC
Essential Therapeutics, Inc., 850Maude Avenue, Mountain View, CA 94043, USA. rlemoine@etrx.com
Magon
Angela
A
Hecker
Scott J
SJ
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis*; D000890:Anti-Infective Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D002236:Carbohydrate Conformation; D002241:Carbohydrates / Q000737:chemistry*; D010455:Peptides; D011741:Pyrimidine Nucleosides / Q000138:chemical synthesis*; D013329:Structure-Activity Relationship; D017855:Transferases (Other Substituted Phosphate Groups) / Q000378:metabolism*; D014498:Uracil / Q000737:chemistry*
D000900:Anti-Bacterial Agents; D000890:Anti-Infective Agents; D002241:Carbohydrates; D010455:Peptides; D011741:Pyrimidine Nucleosides; C432124:dihydropacidamycin D; D014498:Uracil; D017855:Transferases (Other Substituted Phosphate Groups); C100130:phospho-N-acetylmuramoyl pentapeptide transferase