Thioamide-Containing Peptides and Proteins

Barrett, Taylor M.; Fiore, Kristen E.; Liu, Chunxiao; Petersson, E. James

doi:10.1007/978-981-13-7828-7_8

“…This hydrogen bond would be expected to be stronger for the thioamide than for the amide. 5,65 This may explain why both the R S 3A and R S 1A peptides can effectively inhibit Cts L.…”

Section: Resultsmentioning

confidence: 99%

Rational design of thioamide peptides as selective inhibitors of cysteine protease cathepsin L

Phan

¹

,

Giannakoulias

²

,

Barrett

³

et al. 2021

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Construction of Thioamide Peptides from Chiral Amino Acids

Liao

¹

,

Zhang

²

,

Jiang

³

2023

Angewandte Chemie

0

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Thioamide peptides were synthesized in a straightforward one‐pot process via the linkage of diverse natural amino acids in the presence of thiolphosphonate and trichlorosilane, wherein carbonyl groups were replaced with thiono compounds with minimal racemization. Experimental and computational mechanistic studies demonstrated that the trichlorosilane enables the activation of carboxylic acids via intense interactions with the Si−O bond, followed by coupling of the carboxylic acids with thiolphosphonate to obtain the key intermediate S‐acyl dithiophosphate. Silyl‐activated quadrangular metathesis transition states afforded the thioamide peptides. The potential applications of these thioamide peptides were further highlighted via late‐stage linkages of diverse natural products and pharmaceutical drugs and the thioamide moiety.

show abstract

Construction of Thioamide Peptides from Chiral Amino Acids

Liao

¹

,

Zhang

²

,

Jiang

³

2023

View full text Add to dashboard Cite

Thioamide peptides were synthesized in a straightforward one‐pot process via the linkage of diverse natural amino acids in the presence of thiolphosphonate and trichlorosilane, wherein carbonyl groups were replaced with thiono compounds with minimal racemization. Experimental and computational mechanistic studies demonstrated that the trichlorosilane enables the activation of carboxylic acids via intense interactions with the Si−O bond, followed by coupling of the carboxylic acids with thiolphosphonate to obtain the key intermediate S‐acyl dithiophosphate. Silyl‐activated quadrangular metathesis transition states afforded the thioamide peptides. The potential applications of these thioamide peptides were further highlighted via late‐stage linkages of diverse natural products and pharmaceutical drugs and the thioamide moiety.

show abstract

Thioamide-Containing Peptides and Proteins

Cited by 3 publications

References 175 publications

Rational design of thioamide peptides as selective inhibitors of cysteine protease cathepsin L

Rational design of thioamide peptides as selective inhibitors of cysteine protease cathepsin L

Construction of Thioamide Peptides from Chiral Amino Acids

Construction of Thioamide Peptides from Chiral Amino Acids

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