Radamycin, a Novel Thiopeptide Produced by Streptomyces sp. RSP9. II. Physico-chemical Properties and Structure Determination.

Rodriguez, Julian Castro; Holgado, Gloria Gonzalez; Sanchez, Ramon I. Santamaria; Cañedo, Librada M.

doi:10.7164/antibiotics.55.391

Cited by 19 publications

(9 citation statements)

References 2 publications

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“…11 As a result, six thiazole units were determined by the following longrange correlations; in the HMBC spectrum, the thiazole ring proton signal at d 8.43 (H-9) showed long-range couplings to carbons at Finally, each substructure was connected by the long-range correlations of the HMBC technique from the amide proton (H-6) to the carbonyl carbon (C-7), H-22 to C-28, H-32 to C-37, H-44 to C-45 and H-49 to C-50. Thus, the planar structure of nocardithiocin was determined as shown in Figure 1 and the 1 H and 13 C-NMR spectral data of nocardithiocin are summarized in Table 2.…”

Section: Thiazole Unitsmentioning

confidence: 99%

Nocardithiocin, a novel thiopeptide antibiotic, produced by pathogenic Nocardia pseudobrasiliensis IFM 0757

et al. 2009

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Nocardithiocin is a novel thiopeptide compound produced by the pathogenic Nocardia pseudobrasiliensis strain IFM 0757. It shows a strong activity against acid-fast bacilli such as the Mycobacterium and Gordonia species. Nocardithiocin was highly active against rifampicin-resistant as well as -sensitive Mycobacterium tuberculosis strains, and most of the resistant strains were inhibited at concentrations ranging from 0.025 to 1.56 lg ml À1 . The structure of the thiopeptide antibiotic containing thiazole, natural and unnatural amino acids was elucidated by MS and NMR spectral analyses.

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Section: Thiazole Unitsmentioning

confidence: 99%

Nocardithiocin, a novel thiopeptide antibiotic, produced by pathogenic Nocardia pseudobrasiliensis IFM 0757

et al. 2009

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“…It is worth mentioning that cobalt or cobalamin must be present in the cultivation medium. The addition of these compounds strongly affects the ratio of individual antibiotics, due mainly to the fact that it increases methionine biosynthesis and the incorporation of methyl groups into the antibiotic [49][50][51]. Geninthiocin (67) was isolated from Streptomyces sp.…”

Section: Trisubstituted Pyridinesmentioning

confidence: 99%

Pharmacologically Active Sulfur-Containing Compounds

Řezanka¹,

Sobotka²,

Spížek³

et al. 2006

AIAMC

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In addition to sulfur-containing compounds that form essential and indispensable constituents of all living cells, there is a plethora of less wide-spread sulfur-containing compounds with much less common and often unexpected properties, chemical structures and biological activities. Some of these compounds have long been known as efficient antibiotics. This review surveys these less known compounds with two and more sulfur atoms in their molecule. In particular, it deals with natural heterocyclic compounds isolated, e.g., from bacteria, fungi, lichens, plants, and animals but also from unusual and exotic sources such as sea invertebrates (coelenterates, sponges, tunicates, sea worms), etc. Compounds such as calicheamicins, thiazole-related compounds and epipolythiodioxopiperazines may serve as examples. Because of their vast variety, individual compounds are grouped according to their chemical structure (only compounds whose chemical structure has been identified are included). These compounds affect a huge array of organisms from microorganisms to man, and the pharmacological activities they exert range from antiviral, antibacterial, antifungal, insecticidal or antiprotozoan effects to regulation of gene expression, cytoskeleton disruption, immunomodulation, plant growth stimulation or inhibition, pro-or antioxidant action, effects on selected enzymes, receptors and signal transduction pathways, etc. The activities are however often known only sketchily, and this paucity of data, and the fact that the activities were tested on a diverse spectrum of test organisms, cell lines, etc., is of necessity reflected in our survey. Two seemingly trivial but important points deserve attention: (a) compounds with widely different structures and from widely different sources have often very similar pharmacological effects; (b) a slight modification in the molecule may bring vast changes in the biological effects of the compound, in terms of quality, quantity and targeting. The purpose of the review was to show both the unique and common features of these compounds and to point out their potential usefulness for mankind.

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“…Residues with thiazole ring have the most diverse side chains among other rings (thiazoline, oxazole, and oxazoline). Literature survey reveals that in natural compounds they can be found as thiazole- glycine (Kai et al 2012 ; Debono et al 1992 ; Engelhardt et al 2010 ; Jüttner et al 2001 ) , alanine (Kai et al 2012 ; Bagley et al 2000 ; Castro Rodríguez et al 2002 ; Engelhardt et al 2010 ) , valine (Bagley et al 2005 ; Hughes and Moody 2007 ; Bertram and Pattenden 2007 ; Jüttner et al 2001 ) , serine (Zhang et al 2009 ) , methionine (Jüttner et al 2001 ) , threonine (Davyt and Serra 2010 ) , leucine (Davyt and Serra 2010 ) , isoleucine (Jüttner et al 2001 ) , asparagine (Zhang and Liu 2013 ; Young and Walsh 2011 ) , phenylalanine (Davyt and Serra 2010 ) , dehydroalanine (Aoki et al 1991 ) , dehydrobutyrine (Kai et al 2012 ; Walsh et al 2010 ) and other (Bagley et al 2005 ; Jin 2011 ). The important feature of the thiazole ring is the presence of the sp 2 sulfur atom which has a larger size than carbon, nitrogen, or oxygen, and its ability to engage in donating n o → σ* interaction (σ-holes) with the lone pairs of neighbouring heteroatoms.…”

Section: Introductionmentioning

confidence: 99%

Thiazole–amino acids: influence of thiazole ring on conformational properties of amino acid residues

2021

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Post-translational modified thiazole–amino acid (Xaa–Tzl) residues have been found in macrocyclic peptides (e.g., thiopeptides and cyanobactins), which mostly inhibit protein synthesis in Gram + bacteria. Conformational study of the series of model compounds containing this structural motif with alanine, dehydroalanine, dehydrobutyrine and dehydrophenylalanine were performed using DFT method in various environments. The solid-state crystal structure conformations of thiazole–amino acid residues retrieved from the Cambridge Structural Database were also analysed. The studied structural units tend to adopt the unique semi-extended β2 conformation; which is stabilised mainly by N–H⋯NTzl hydrogen bond, and for dehydroamino acids also by π-electron conjugation. The conformational preferences of amino acids with a thiazole ring were compared with oxazole analogues and the role of the sulfur atom in stabilising the conformations of studied peptides was discussed.

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Radamycin, a Novel Thiopeptide Produced by Streptomyces sp. RSP9. II. Physico-chemical Properties and Structure Determination.

Cited by 19 publications

References 2 publications

Nocardithiocin, a novel thiopeptide antibiotic, produced by pathogenic Nocardia pseudobrasiliensis IFM 0757

Nocardithiocin, a novel thiopeptide antibiotic, produced by pathogenic Nocardia pseudobrasiliensis IFM 0757

Pharmacologically Active Sulfur-Containing Compounds

Thiazole–amino acids: influence of thiazole ring on conformational properties of amino acid residues

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