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Organometallic AlaM reagents for umpolung peptide diversification

https://doi.org/10.1016/j.checat.2021.05.016

Zhu, Feng ; Powell, Wyatt C. ; Jing, Ruiheng ; Walczak, Maciej A. ( September 2021 , Chem Catalysis)

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Umpolung Ala ^B Reagents for the Synthesis of Non‐Proteogenic Amino Acids, Peptides and Proteins**

https://doi.org/10.1002/anie.202207153

Zhu, Feng ; Miller, Eric ; Powell, Wyatt C. ; Johnson, Kelly ; Beggs, Alexander ; Evenson, Garrett E. ; Walczak, Maciej A. ( June 2022 , Angewandte Chemie International Edition)

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Umpolung Ala ^B Reagents for the Synthesis of Non‐Proteogenic Amino Acids, Peptides and Proteins**

https://doi.org/10.1002/ange.202207153

Zhu, Feng ; Miller, Eric ; Powell, Wyatt C. ; Johnson, Kelly ; Beggs, Alexander ; Evenson, Garrett E. ; Walczak, Maciej A. ( June 2022 , Angewandte Chemie)

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Total synthesis of micrococcin P1 and thiocillin I enabled by Mo( vi ) catalyst

https://doi.org/10.1039/c8sc04885a

Akasapu, Siddhartha ; Hinds, Aaron B. ; Powell, Wyatt C. ; Walczak, Maciej A. ( February 2019 , Chemical Science)

Thiopeptides are a class of potent antibiotics with promising therapeutic potential. We developed a novel Mo( vi )-oxide/picolinic acid catalyst for the cyclodehydration of cysteine peptides to form thiazoline heterocycles. With this powerful tool in hand, we completed the total syntheses of two representative thiopeptide antibiotics: micrococcin P1 and thiocillin I. These two concise syntheses (15 steps, longest linear sequence) feature a C–H activation strategy to install the trisubstituted pyridine core and thiazole groups. The synthetic material displays promising antimicrobial properties measured against a series of Gram-positive bacteria.

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