Chemo-enzymatic total syntheses of bis-tetrahydroisoquinoline alkaloids and systematic exploration of the substrate scope of SfmC

Chemo-enzymatic hybrid process merging enzymatic cascade reactions of designed substrates with chemo- and site-selective synthetic manipulations allowed the chemo-enzymatic total syntheses of jorunnamycin A and saframycin A, in just 4 and 5 pots processes, respectively. Artificial variants with inst...

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Bibliographic Details
Published in:Tetrahedron chem 2022-03, Vol.1, p.100010, Article 100010
Main Authors: Tanifuji, Ryo, Haraguchi, Naoto, Oguri, Hiroki
Format: Article
Language:English
Subjects:
Chemo-enzymatic synthesis
Non-ribosomal peptide synthetase
Tetrahydroisoquinoline alkaloids
Total synthesis
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Summary:Chemo-enzymatic hybrid process merging enzymatic cascade reactions of designed substrates with chemo- and site-selective synthetic manipulations allowed the chemo-enzymatic total syntheses of jorunnamycin A and saframycin A, in just 4 and 5 pots processes, respectively. Artificial variants with installation of various amino acids in place of l-Ala were systematically generated, demonstrating the substantially broader substrate scope of SfmC. This chemo-enzymatic hybrid process can considerably minimize the number of steps, labor, and time, and thus offer a rapid and versatile means to generate therapeutically important natural products and their derivatives. [Display omitted]
ISSN:2666-951X
2666-951X
DOI:10.1016/j.tchem.2022.100010