Biosystems Chemistry, Department of Chemistry and Center for Integrated Protein Science Munich (CIPSM), Technical University of Munich, Lichtenbergstrasse 4, 85748, Garching, Germany.
Angew Chem Int Ed Engl. 2018 Oct 26;57(44):14650-14653. doi: 10.1002/anie.201802176. Epub 2018 Jun 25.
The sorbicillinoids are a large family of fungal natural products, many of which possess highly challenging molecular architectures. Depending on their individual structures they exhibit strong biological activities ranging from radical scavenging and anti-infective properties to cytotoxicity. Despite the resulting strong biomedical potential of these natural products and the interest of synthetic chemists owing to their fascinating structures, many sorbicillinoids are currently not synthetically accessible, thus hampering in-depth biological characterization and structural diversification. By using recombinant oxidoreductase SorbC and readily accessible sorbicillin-type synthetic precursors, we have developed enantioselective, one-pot chemo-enzymatic routes to a broad range of sorbicillinoids, thereby establishing total syntheses of oxosorbicillinol, sorrentanone, rezishanones B and C, sorbicatechol A, bisvertinolone, and (+)-epoxysorbicillinol.
山梨醇菌素是一大类真菌天然产物，其中许多具有极具挑战性的分子结构。根据其各自的结构，它们表现出从清除自由基和抗感染特性到细胞毒性的强烈的生物活性。尽管这些天然产物具有很强的生物医学潜力，而且由于其迷人的结构，合成化学家也很感兴趣，但许多山梨醇菌素目前无法通过合成获得，因此阻碍了深入的生物学特征分析和结构多样化。通过使用重组氧化还原酶 SorbC 和易于获得的山梨醇型合成前体，我们开发了对映选择性、一锅式的化学酶法途径来合成广泛的山梨醇菌素，从而建立了氧代山梨醇醇、山梨坦酮、雷山酮 B 和 C、山梨醇 A、双维醇酮和（+）-环氧山梨醇醇的全合成。
