A Convergent Strategy for the Pamamycin Macrodiolides: Total Synthesis of Pamamycin‐607, Pamamycin‐593, and Pamamycin‐621D Precursors

Lanners, Steve; Norouzi‐Arasi, Hassan; Salom‐Roig, Xavier J.; Hanquet, Gilles

doi:10.1002/ange.200701749

Cited by 5 publications

(1 citation statement)

References 33 publications

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“…Solvent-accessible surface bounded molecular volume and van der Waals-surfacebounded molecular volume calculations are based on a grid method derived by Bodor et al [50], using the atomic radii of Gavezotti [51].…”

Section: Solvent-accessible Surfacementioning

confidence: 99%

Conformational Analysis, Substituent Effect and Structure Activity Relationships of 16-Membered Macrodiolides

Mazri

Belaidi

Kerassa

et al. 2014

ILCPA

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Electronic structures, Conformational Analysis, effect of the substitution and structure activity Relationships for macrodiolides, have been studied by PM3 and ab initio methods. In the present work, the calculated values, namely net charges, bond lengths, MESP, dipole moments, electronaffinities, heats of formation, drug-likeness and QSAR properties, are reported and discussed in terms of the biological activity of macrodiolides.

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Section: Solvent-accessible Surfacementioning

confidence: 99%

Conformational Analysis, Substituent Effect and Structure Activity Relationships of 16-Membered Macrodiolides

Mazri

Belaidi

Kerassa

et al. 2014

ILCPA

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Einblicke in die Pamamycin‐Biosynthese

et al. 2014

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Pamamycine sind Makrodiolide polyketider Herkunft, die antibakteriell wirken. Es wurde postuliert, dass ihre Biosynthese Succinat als Baustein verwendet. Jedoch war der Mechanismus des Succinat-Einbaus in ein Polyketid unklar. Hier berichten wir über die Identifizierung eines Pamamycin-Biosynthese-Genclusters durch Vergleich der Genome zweier Pamamycin-produzierender Stämme. Dieses einzigartige Cluster enthält Polyketid-Biosynthese(PKS)-Gene, die für sieben verschiedene Ketosynthase(KS)-Enzyme codieren und ein Gen, das ein Acyl-Transporter-Protein (ACP) codiert. Ein Cosmid, welches das vollständige Set an Genen zur Pamamycin-Biosynthese trägt, wurde erfolgreich in einem heterologen Wirt exprimiert. Genetische und biochemische Studien führten zur vollständigen Aufklärung der Pamamycin-Biosynthese. Diese führt über 3-Oxoadipyl-CoA, ein Schlüsselintermediat des Abbaus von aromatischen Verbindungen des Primärstoffwechsels, das in der Polyketid-Synthese den Einbau von Succinat ermçglichen kçnnte. Hintergrundinformationen zu diesem Beitrag sind im WWW unter http://dx.

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Insights into the Pamamycin Biosynthesis

et al. 2014

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Pamamycins are macrodiolides of polyketide origin with antibacterial activities. Their biosynthesis has been proposed to utilize succinate as a building block. However, the mechanism of succinate incorporation into a polyketide was unclear. Here, we report identification of a pamamycin biosynthesis gene cluster by aligning genomes of two pamamycin-producing strains. This unique cluster contains polyketide synthase (PKS) genes encoding seven discrete ketosynthase (KS) enzymes and one acyl-carrier protein (ACP)-encoding gene. A cosmid containing the entire set of genes required for pamamycin biosynthesis was successfully expressed in a heterologous host. Genetic and biochemical studies allowed complete delineation of pamamycin biosynthesis. The pathway proceeds through 3-oxoadipyl-CoA, a key intermediate in the primary metabolism of the degradation of aromatic compounds. 3-Oxoadipyl-CoA could be used as an extender unit in polyketide assembly to facilitate the incorporation of succinate.

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A Convergent Strategy for the Pamamycin Macrodiolides: Total Synthesis of Pamamycin‐607, Pamamycin‐593, and Pamamycin‐621D Precursors

Cited by 5 publications

References 33 publications

Conformational Analysis, Substituent Effect and Structure Activity Relationships of 16-Membered Macrodiolides

Conformational Analysis, Substituent Effect and Structure Activity Relationships of 16-Membered Macrodiolides

Einblicke in die Pamamycin‐Biosynthese

Insights into the Pamamycin Biosynthesis

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