Abstract
Chemoenzymatic synthesis of complex natural and unnatural products: morphine, pancratistatin, and their analogs
Highlights
Recombinant strains that express toluene dioxygenase (TDO) are used to provide the homochiral diene cis-diol derived from bromobenzene and containing the structural features of both ring C of morphine and ring C of pancratistatin
To approach the synthesis of highly oxygenated targets such as pancratistatin and morphine, we designed a general strategy based on the recognition of common elements shared by the structures
One strategy that relies on aromatic dioxygenases starts with biphenyl and its oxygenation with an organism that expresses both TDO and DHDH, yielding directly a catechol
Summary
Recombinant strains that express toluene dioxygenase (TDO) are used to provide the homochiral diene cis-diol derived from bromobenzene and containing the structural features of both ring C of morphine and ring C of pancratistatin. Gibson elucidated the degradation pathway by which soil bacteria utilize arenes as carbon and energy source, and he provided key recombinant organisms for the whole-cell fermentation production of diols such as 4.6 Toluene dioxygenase (TDO) is overexpressed in E. coli JM109(pDTG601) and provides, with good substrates such as bromobenzene, 20 g/L of the corresponding bromochiral diol 5.
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