Oxidative diversification of amino acids and peptides by small-molecule iron catalysis was written by Osberger, Thomas J.;Rogness, Donald C.;Kohrt, Jeffrey T.;Stepan, Antonia F.;White, M. Christina. And the article was included in Nature (London, United Kingdom) in 2016.Computed Properties of C9H8S This article mentions the following:
Secondary metabolites synthesized by non-ribosomal peptide synthetases display diverse and complex topologies and possess a range of biol. activities. Much of this diversity derives from a synthetic strategy that entails pre- and post-assembly oxidation of both the chiral amino acid building blocks and the assembled peptide scaffolds. The vancomycin biosynthetic pathway is an excellent example of the range of oxidative transformations that can be performed by the iron-containing enzymes involved in its biosynthesis. However, because of the challenges associated with using such oxidative enzymes to carry out chem. transformations in vitro, chem. syntheses guided by these principles have not been fully realized in the laboratory Here we report that two small-mol. iron catalysts are capable of facilitating the targeted C-H oxidative modification of amino acids and peptides with preservation of α-center chirality. Oxidation of proline to 5-hydroxyproline furnishes a versatile intermediate that can be transformed to rigid arylated derivatives or flexible linear carboxylic acids, alcs., olefins and amines in both monomer and peptide settings. The value of this C-H oxidation strategy is demonstrated in its capacity for generating diversity: four ‘chiral pool’ amino acids are transformed to twenty-one chiral unnatural amino acids representing seven distinct functional group arrays; late-stage C-H functionalizations of a single proline-containing tripeptide furnish eight tripeptides, each having different unnatural amino acids. Addnl., a macrocyclic peptide containing a proline turn element is transformed via late-stage C-H oxidation to one containing a linear unnatural amino acid. In the experiment, the researchers used many compounds, for example, 2-Methylbenzo[b]thiophene (cas: 1195-14-8Computed Properties of C9H8S).
2-Methylbenzo[b]thiophene (cas: 1195-14-8) belongs to benzothiophene derivatives. Benzothiophene scaffolds are of great importance due to its increased presence in bioactive molecules. It has been used as a raw material for the synthesis of biologically active structures and is found in pharmaceuticals such as leukotriene synthesis inhibitors and antifungals, as well as in many natural products.Computed Properties of C9H8S
Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem