| Structure Identification: |
| Org Lett. 2015 Feb 6;17(3):628-31. | | Discovery of a new family of Dieckmann cyclases essential to tetramic acid and pyridone-based natural products biosynthesis.[Pubmed: 25621700] |
METHODS AND RESULTS:
Bioinformatic analyses indicate that TrdC, SlgL, LipX2, KirHI, and FacHI belong to a group of highly homologous proteins involved in biosynthesis of actinomycete-derived tirandamycin B, streptolydigin, α-lipomycin, kirromycin, and factumycin, respectively. However, assignment of their biosynthetic roles has remained elusive.
CONCLUSIONS:
Gene inactivation and complementation, in vitro biochemical assays with synthetic analogues, point mutations, and phylogenetic tree analyses reveal that these proteins represent a new family of Dieckmann cyclases that drive tetramic acid and pyridone scaffold biosynthesis. | | Angew Chem Int Ed Engl. 2014 Jul 7;53(28):7328-34. | | α- and β-Lipomycin: total syntheses by sequential stille couplings and assignment of the absolute configuration of all stereogenic centers.[Pubmed: 24895187] | 40 years ago spectroscopy, derivatization, and degradation revealed the structures of alpha-Lipomycin and its aglycon β-lipomycin except for the configurations of their side-chain stereocenters.
METHODS AND RESULTS:
We synthesized all relevant β-lipomycin candidates: the (12R,13S) isomer has the same specific rotational value as the natural product. By the same criterion the (12R,13S)-configured D-digitoxide is identical to alpha-Lipomycin.
CONCLUSIONS:
We double-checked our assignments by degrading alpha-Lipomycin and β-lipomycin to the diesters 33 and 34 and proving their 3D structures synthetically. |
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