Bacitracin is a dodecapeptide antibiotic produced by Bacillus sp. The antibacterial activity depends upon the peptide binding a divalent metal. Hitherto, the exact coordination of the cation has not been established. In particular the role played by the sulphur and nitrogen atoms of the thiazoline ring of bacitracin A has not been clear. Here the coordination of Zn2+ by bacitracin A has been st...

The crystal structures of 2-amino-2-thiazoline, C3H6N2S, and 2-amino-2-thiazolinium 2-naphthoxyacetate, C3H7N2S+.C12H9O3-, are reported. The structure of 2-amino-2-thiazoline consists of two unique molecules that construct a convoluted hydrogen-bonded ribbon involving R(2)2(8) graph-set association via both N-H...N and N-H...S interactions. The organic salt structure consists of the two molecul...

A new series of 2-hydrazone-thiazoline-4-ones 3a-d and 2-hydrazone-5arylidene-thiazoline-4-ones 4a-h, 5a-f and 6a-b were synthesized starting from various thiosemicarbazones by the Hantzsch condensation with chloroacetic acid. The newly synthesized compounds were screened for their antimicrobial activity against 4 strains of bacteria: Staphylococcus aureus (ATCC 29213), Bacillus subtilis (ATCC ...

Human milk oligosaccharides contain a large variety of oligosaccharides, of which lacto-N-biose I (Gal-β1,3-GlcNAc; LNB) predominates as a major core structure. A unique metabolic pathway specific for LNB has recently been identified in the human commensal bifidobacteria. Several strains of infant gut-associated bifidobacteria possess lacto-N-biosidase, a membrane-anchored extracellular enzyme,...

The natural products epothilone and bleomycin are assembled by hybrid polyketide/nonribosomal peptide synthetases. Of note in these assembly lines is the conversion of internal cysteine residues into thiazolines and their subsequent oxidation to heteroaromatic thiazole rings. We have excised the EpoB oxidase domain, EpoB-Ox, proposed to be responsible for thiazoline to thiazole oxidation in epo...

Spurred by the alleged relevance of the thia-Michael reaction in the bioactivity of various classes of cinnam(o)yl natural products and by the development of a quick NMR assay to study this reaction, we have carried out a systematic study of the "native" reactivity of these compounds with dodecanethiol and cysteamine as models, respectively, of simple thiols and reactive protein thiols that can...