Biosynthesis and chemical applications of thioamides

N Mahanta, DM Szantai-Kis, EJ Petersson… - ACS chemical …, 2019 - ACS Publications
Thioamidation as a posttranslational modification is exceptionally rare, with only a few
reported natural products and exactly one known protein example (methyl-coenzyme M …

Unnatural Amino Acids for Biological Spectroscopy and Microscopy

R Feng, M Wang, W Zhang, F Gai - Chemical Reviews, 2024 - ACS Publications
Due to advances in methods for site-specific incorporation of unnatural amino acids (UAAs)
into proteins, a large number of UAAs with tailored chemical and/or physical properties have …

Thioamide Analogues of MHC I Antigen Peptides

R Gibadullin, RK Morris, J Niu, J Sidney… - Journal of the …, 2023 - ACS Publications
Short, synthetic peptides that are displayed by major histocompatibility complex I (MHC I)
can stimulate CD8 T cells in vivo to destroy virus-infected or cancer cells. The development …

A prevalent intraresidue hydrogen bond stabilizes proteins

RW Newberry, RT Raines - Nature chemical biology, 2016 - nature.com
Current limitations in de novo protein structure prediction and design suggest an incomplete
understanding of the interactions that govern protein folding. Here we demonstrate that …

Thioamide substitution selectively modulates proteolysis and receptor activity of therapeutic peptide hormones

X Chen, EG Mietlicki-Baase, TM Barrett… - Journal of the …, 2017 - ACS Publications
Peptide hormones are attractive as injectable therapeutics and imaging agents, but they
often require extensive modification by mutagenesis and/or chemical synthesis to prevent …

Three-component reaction between alkynes, elemental sulfur, and aliphatic amines: a general, straightforward, and atom economical approach to thioamides

TB Nguyen, MQ Tran, L Ermolenko… - Organic letters, 2014 - ACS Publications
Three-Component Reaction between Alkynes, Elemental Sulfur, and Aliphatic Amines: A
General, Straightforward, and Atom Economical Approach to Thioamides | Organic Letters …

Synergistic Effects of Unconventional Hydrogen Bonds and π-Stacking Interaction and Their Excited-State Dependence: The Origin of Unusual Photophysical …

YG Fang, C Zhu, L Shen, H Wang… - Journal of the American …, 2024 - ACS Publications
It has been established experimentally that aromatic thioketones possess several inherently
unique photophysical properties, some of which are highly sensitive even to common …

The effects of thioamide backbone substitution on protein stability: a study in α-helical, β-sheet, and polyproline II helical contexts

CR Walters, DM Szantai-Kis, Y Zhang, ZE Reinert… - Chemical …, 2017 - pubs.rsc.org
Thioamides are single atom substitutions of the peptide bond that serve as versatile probes
of protein structure. Effective use of thioamides requires a robust understanding of the …

Increasing the bioactive space of peptide macrocycles by thioamide substitution

H Verma, B Khatri, S Chakraborti, J Chatterjee - Chemical Science, 2018 - pubs.rsc.org
We show that substituting a single atom, O to S (amide to thioamide), in a peptide bond
results in global restriction of the conformational flexibility in peptide macrocycles with …

Increasing protein stability by engineering the n→ π* interaction at the β-turn

B Khatri, P Majumder, J Nagesh, A Penmatsa… - Chemical …, 2020 - pubs.rsc.org
Abundant n→ π* interactions between adjacent backbone carbonyl groups, identified by
statistical analysis of protein structures, are predicted to play an important role in dictating …