To probe noncovalent interactions within the collagen triple helix, backbone amides were replaced with a thioamide isostere. This subtle substitution is the first in the collagen backbone that does not compromise thermostability. A triple helix with a thioamide as a hydrogen bond donor was found to be more stable than triple helices assembled from isomeric thiopeptides.

In the presence of manganese oxides, dehydrosulfurization of various kinds of primary thioamides including aromatic, heterocyclic, and aliphatic ones efficiently proceeded to give the corresponding nitriles in high yields. The observed catalysis was truly heterogeneous, and manganese oxides could be reused.

We herein describe a novel method for the synthesis of thioamides by a three component condensation of alkynyl bromides, amines, and Na2S·9H2O. The developed method is applicable for a wide range of amines and alkynyl bromides bearing different functional groups furnishing the corresponding products in moderate to excellent yields.

A facile one-pot two-step process for the synthesis of 1,3-thiazole heterocycles via organocatalytic epoxidation of nitro-olefins with the t-BuOOH/DBU system, and subsequent reaction of α-nitro-epoxides with thioamides under mild conditions has been developed.

Thioamides quench tryptophan and tyrosine fluorescence in a distance-dependent manner and thus can be used to monitor the binding of thioamide-containing peptides to proteins. Since thioamide analogs of the natural amino acids can be synthetically incorporated into peptides, they can function as minimally-perturbing probes of protein/peptide interactions.

Generation and cycloaddition of less- or non-stabilized azomethine ylides, or nitrile ylide equivalents, via unprecedented 1,4-stannatropy of N-(tributylstannylmethyl)thioamides were achieved. The reactions with dipolarophiles, such as electron-deficient alkenes and alkynes, afforded corresponding pyrrolidine and pyrrole derivatives effectively.

The title compounds, (4-trifluoromethoxyphenyl)-2,5-dimethyl-3-(2-R-thiazol-4-yl)-1H-pyrroles, were prepared in four steps starting from commercially available 4-trifluoromethoxyaniline. The pyrrole (second ring) was added in one step using the Paal-Knorr method. The thiazole (third ring) was added in three steps using chloroacylation with chloroacetonitrile followed by heterocyclization with t...

Elemental gold powder is easily oxidised under mild reaction conditions with 1 : 1 I(2)-adducts of the thioamides 3-methyl-benzothiazole-2-thione (mbtt) and 1-methyl-1H-benzimidazole-2(3H)-thione (mbit) with separation of the ionic complexes [Au(I)(mbtt)(2)]I(3) (1) and [(mtbiH)(2)](AuI(4))I(3) (2) [mtbiH = the imido protonated form of 2-(methylthio)benzimidazole] (gold oxidation yield >78% and...

Thioviridamide is a unique peptide antibiotic containing five thioamide bonds from Streptomyces olivoviridis. Draft genome sequencing revealed a gene (the tvaA gene) encoding the thioviridamide precursor peptide. The thioviridamide biosynthesis gene cluster was identified by heterologous production of thioviridamide in Streptomyces lividans.