Synthesis of proposed oxidation-cyclization-methylation intermediates of the coumarin antibiotic biosynthetic pathway.
[structure: see text] A chemoenzymatic synthesis was described to prepare proposed oxidation-cyclization-methylation intermediates of the coumarin antibiotic biosynthetic pathway. The successful synthesis of these fragile molecules relies heavily on mild enzymatic deprotection and efficient enzymatic kinetic resolution to minimize epimerization, decomposition, multiple orthogonal protections, and retro aldol reactions often encountered in their chemical synthesis.
Tao
Junhua
J
Department of Biological Chemistry and Molecular Pharmacology, Harvard Medical School, 240 Longwood Avenue, Boston, Massachusetts 02115, USA.
Hu
Shanghui
S
Pacholec
Michelle
M
Walsh
Christopher T
CT
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis*; D002384:Catalysis; D003374:Coumarins / Q000138:chemical synthesis*; D003500:Cyclization; D010450:Endopeptidases / Q000737:chemistry; D004950:Esterases / Q000737:chemistry; D007651:Keto Acids / Q000737:chemistry; D007700:Kinetics; D008049:Lipase / Q000737:chemistry; D008745:Methylation; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013237:Stereoisomerism
D000900:Anti-Bacterial Agents; D003374:Coumarins; D007651:Keto Acids; D004950:Esterases; D008049:Lipase; D010450:Endopeptidases