Clathration-induced asymmetric transformation of cefadroxil.
[structure: see text] The cephalosporin antibiotic Cefadroxil can be epimerized at the alpha-carbon of its amino acid side chain using pyridoxal as the mediator. By clathration with 2,7-dihydroxynaphthalene, the desired diastereomer can be selectively withdrawn from the equilibrating mixture of epimers. In this way, an asymmetric transformation of Cefadroxil can be accomplished. This opens the possibility of the production of Cefadroxil starting from racemic p-hydroxyphenylglycine, in contrast to the current industrial synthesis that employs the D-amino acid in enantiopure form.
Kemperman
G J
GJ
Department of Organic Chemistry, NSR Center for Molecular Structure, Design and Synthesis, University of Nijmegen, Toernooiveld 1, 6525 ED Nijmegen, The Netherlands.
Zhu
J
J
Klunder
A J
AJ
Zwanenburg
B
B
D002434:Cefadroxil / Q000138:chemical synthesis* / Q000302:isolation & purification; D002511:Cephalosporins / Q000138:chemical synthesis* / Q000302:isolation & purification; D005998:Glycine / Q000031:analogs & derivatives* / Q000737:chemistry; D009284:Naphthols / Q000737:chemistry; D013237:Stereoisomerism
D002511:Cephalosporins; D009284:Naphthols; C107946:2,7-dihydroxynaphthalene; D002434:Cefadroxil; C023010:4-hydroxyphenylglycine; D005998:Glycine