Total synthesis of exochelin MN and analogues.
The first total synthesis of exochelin MN is described along with rationally designed analogues. The required L-threo-beta-hydroxyamino acid components were constructed using either Sharpless asymmetric aminohydroxylation reactions or an aldol reaction of imidazolidinone 19. A new concise procedure for the preparation of the constituent six-membered cyclic hydroxamate was developed. In addition, a plausible mechanism for exochelin MN-mediated iron(III) transport was proposed. Biological studies of these compounds will be used to evaluate this hypothesis.
Dong
Li
L
Department of Chemistry and Biochemistry, University of Notre Dame, 251 Nieuwland Science Hall, Notre Dame, Indiana 46556-5670, USA.
Miller
Marvin J
MJ
D000596:Amino Acids / Q000737:chemistry; D002384:Catalysis; D002625:Chemistry, Organic / Q000379:methods*; D007501:Iron / Q000378:metabolism; D013058:Mass Spectrometry; D015394:Molecular Structure; D009161:Mycobacterium / Q000737:chemistry*; D019906:Nuclear Magnetic Resonance, Biomolecular; D010456:Peptides, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry; D017262:Siderophores / Q000737:chemistry*; D013237:Stereoisomerism
D000596:Amino Acids; D010456:Peptides, Cyclic; D017262:Siderophores; C469854:exochelin MN; C010953:exochelins; D007501:Iron