title: Synthesis of proposed oxidation-cyclization-methylation intermediates of the coumarin antibiotic biosynthetic pathway.
abstract: [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.
authors.affiliation: Department of Biological Chemistry and Molecular Pharmacology, Harvard Medical School, 240 Longwood Avenue, Boston, Massachusetts 02115, USA.
authors.forename: Junhua
authors.initials: J
authors.lastname: Tao
authors.forename: Shanghui
authors.initials: S
authors.lastname: Hu
authors.forename: Michelle
authors.initials: M
authors.lastname: Pacholec
authors.forename: Christopher T
authors.initials: CT
authors.lastname: Walsh
mesh_terms: 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
chemical_list: D000900:Anti-Bacterial Agents; D003374:Coumarins; D007651:Keto Acids; D004950:Esterases; D008049:Lipase; D010450:Endopeptidases