Formal Synthesis of 6-Deoxyerythronolide B
نویسندگان
چکیده
منابع مشابه
Formal synthesis of 6-deoxyerythronolide B.
[reaction: see text] The enantioselective synthesis of the carbon skeleton of 6-deoxyerythronolide B has been achieved in 23 linear steps from propionaldehyde. The synthesis relies on an iterative approach employing an asymmetric acyl-thiazolidinethione propionate aldol reaction to establish eight of nine stereogenic centers. The remaining stereogenic center at C6 was set through a Myers alkyla...
متن کاملMolecular recognition between ketosynthase and acyl carrier protein domains of the 6-deoxyerythronolide B synthase.
Every polyketide synthase module has an acyl carrier protein (ACP) and a ketosynthase (KS) domain that collaborate to catalyze chain elongation. The same ACP then engages the KS domain of the next module to facilitate chain transfer. Understanding the mechanism for this orderly progress of the growing polyketide chain represents a fundamental challenge in assembly line enzymology. Using both ex...
متن کاملReprogramming a module of the 6-deoxyerythronolide B synthase for iterative chain elongation.
Multimodular polyketide synthases (PKSs) have an assembly line architecture in which a set of protein domains, known as a module, participates in one round of polyketide chain elongation and associated chemical modifications, after which the growing chain is translocated to the next PKS module. The ability to rationally reprogram these assembly lines to enable efficient synthesis of new polyket...
متن کاملArchitectures of whole-module and bimodular proteins from the 6-deoxyerythronolide B synthase.
The 6-deoxyerythronolide B synthase (DEBS) is a prototypical assembly line polyketide synthase produced by the actinomycete Saccharopolyspora erythraea that synthesizes the macrocyclic core of the antibiotic erythromycin 6-deoxyerythronolide B. The megasynthase is a 2-MDa trimeric complex composed of three unique homodimers assembled from the gene products DEBS1, DEBS2, and DEBS3, which are hou...
متن کاملProbing the heterologous metabolism supporting 6‐deoxyerythronolide B biosynthesis in Escherichia coli
Heterologous biosynthesis offers a new way to capture the medicinal properties presented by complex natural products. In this study, production of 6-deoxyerythronolide B (6dEB), the polyketide precursor to the antibiotic erythromycin, was used to probe the heterologous pathways needed for Escherichia coli-derived biosynthesis. More specifically, the heterologous proteins responsible for 6dEB pr...
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ژورنال
عنوان ژورنال: Organic Letters
سال: 2006
ISSN: 1523-7060,1523-7052
DOI: 10.1021/ol0607241