Synthesis of a conformationally restricted substrate analogue of siderophore biosynthetases.
[reaction: see text] A conformationally restricted analogue (5) of N(omega)-acetyl-N(omega)-hydroxyornithine and -lysine was synthesized. The synthesis features an efficient acylnitroso hetero-Diels-Alder cycloadduct (1) ring opening with palladium(0) and methylnitroacetate.
Surman
M D
MD
Department of Chemistry and Biochemistry, University of Notre Dame, Indiana 46556, USA.
Miller
M J
MJ
D002384:Catalysis; D008239:Lysine / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009952:Ornithine / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry; D007652:Oxo-Acid-Lyases / Q000378:metabolism*; D010165:Palladium / Q000737:chemistry; D017262:Siderophores / Q000378:metabolism*; D013329:Structure-Activity Relationship; D013379:Substrate Specificity
C423353:N(omega)-acetyl-N(omega)-hydroxyornithine; D017262:Siderophores; D010165:Palladium; C049468:N(6)-acetyl-N(6)-hydroxylysine; D009952:Ornithine; D007652:Oxo-Acid-Lyases; C047194:aerobactin synthetase; D008239:Lysine