Stereoselective syntheses of 4-oxa diaminopimelic acid and its protected derivatives via aziridine ring opening.
Regio- and stereoselective aziridine ring opening with oxygen nucleophiles derived from serine and threonine provides a route to stereochemically pure 4-oxa-2,6-diaminopimelic acid (oxa-DAP) and its methyl-substituted derivatives. Oxa-DAP is a substrate of DAP epimerase, a key enzyme for biosynthesis of l-lysine and formation of peptidoglycan precursors. Orthogonally protected analogues of lanthionine and beta-methyllanthionine wherein oxygen replaces sulfur were prepared that could be used for solid-supported peptide synthesis to make oxa derivatives of lantibiotics.
Liu
Hongqiang
H
Department of Chemistry, University of Alberta, Edmonton, Alberta, Canada T6G 2G2.
Pattabiraman
Vijaya R
VR
Vederas
John C
JC
D000409:Alanine / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry; D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D001388:Aziridines / Q000737:chemistry*; D002384:Catalysis; D003960:Diaminopimelic Acid / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry; D006193:Haemophilus influenzae / Q000201:enzymology; D015394:Molecular Structure; D019998:Racemases and Epimerases / Q000378:metabolism; D012694:Serine / Q000737:chemistry; D013237:Stereoisomerism; D013440:Sulfides / Q000138:chemical synthesis / Q000737:chemistry; D013912:Threonine / Q000737:chemistry
C524150:4-oxa-2,6-diaminopimelic acid; D000596:Amino Acids; D001388:Aziridines; D013440:Sulfides; D013912:Threonine; D012694:Serine; C033132:aziridine; D003960:Diaminopimelic Acid; D019998:Racemases and Epimerases; C001520:lanthionine; D000409:Alanine