Sulfomycins, a Series of New Sulfur-Containing Antibiotics. I

Egawa, Yoshiyuki; Umino, Kimio; Tamura, Yoshikazu; Shimizu, Masaaki; Kaneko, Kenyo; Sakurazawa, Masaharu; Awataguchi, Shigemi; Okuda, Tomoharu

doi:10.7164/antibiotics.22.12

Cited by 42 publications

(23 citation statements)

References 1 publication

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“…The molecular basis of thiazolylpyridine macrocyclic ring size as determinant of ribosomal versus elongation factor targeting is not yet known. One additional macrocyclic ring size in the thiopeptide antibiotic class is represented by the berninamycins, sulfomycin (19), thioplabin (20), and TP-1161A (21,22). This class has a unique oxazolyl-thiazolyl-pyridine core embedded in a 35-membered (13-residue) peptidyl macrocycle ( Fig.…”

mentioning

confidence: 99%

The posttranslational modification cascade to the thiopeptide berninamycin generates linear forms and altered macrocyclic scaffolds

Malcolmson

Young

Ruby

et al. 2013

Proc. Natl. Acad. Sci. U.S.A.

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Berninamycin is a member of the pyridine-containing thiopeptide class of antibiotics that undergoes massive posttranslational modifications from ribosomally generated preproteins. Berninamycin has a 2-oxazolyl-3-thiazolyl-pyridine core embedded in a 35-atom macrocycle rather than typical trithiazolylpyridine cores embedded in 26-atom and 29-atom peptide macrocycles. We describe the cloning of an 11-gene berninamycin cluster from Streptomyces bernensis UC 5144, its heterologous expression in Streptomyces lividans TK24 and Streptomyces venezuelae ATCC 10712, and detection of variant and incompletely processed scaffolds. Posttranslational maturation in S. lividans of both the wild-type berninamycin prepeptide (BerA) and also a T3A mutant generates macrocyclic compounds as well as linear variants, which have failed to form the pyridine and the macrocycle. Expression of the gene cluster in S. venezuelae generates a variant of the 35-atom skeleton of berninamycin, containing a methyloxazoline in the place of a methyloxazole within the macrocyclic framework.heterologous expression | linear precursors | prepeptide gene replacement

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mentioning

confidence: 99%

The posttranslational modification cascade to the thiopeptide berninamycin generates linear forms and altered macrocyclic scaffolds

Malcolmson

Young

Ruby

et al. 2013

Proc. Natl. Acad. Sci. U.S.A.

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“…sulfomycini [44,45]. All sulfomycins exhibit a high activity against Gram-positive bacteria including methicillin-resistant Staphylococcus aureus and, as expected, do not inhibit Gram-negative species ( Table 2).…”

Section: Trisubstituted Pyridinesmentioning

confidence: 74%

“…Siomycins (34-37) isolated from Streptomyces sioyaensis and active against Gram-positive bacteria and mycobacteria [28,29] represent another group of compounds. The thiopeptins (38)(39)(40)(41)(42)(43)(44)(45) [30,31]. Sch 18640, isolated from Micromonospora arborensis [32], may serve as a representative of compounds produced by a microorganism different from Streptomyces.…”

Section: Piperidines and Dehydropiperidinesmentioning

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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“…Both compounds are thiopeptide antibiotics [200,201] , characterized by several common structural features, such as oxazole and thiazole units and unusual amino acids; especially dehydroamino acids are typical [202,203] . Among this group are thioxamycin [204] , berninamycin A [205] , sulfomycin I [206][207][208] and A10255 [209] , possessing the thiazole-pyridine-oxazole substructure. Moreover, thiocillin I [210,211] , micrococcin P [212] and GE2270 A [213] are thiopeptides characterized by a thiazole-pyridine-thiazole moiety.…”

Section: Thz Thrmentioning

confidence: 99%

“…Tü 6368 [312,313] . Lumichrome (201), a metabolite of riboflavin (206), competed with 3 Hlabeled tetrachlorodibenzodioxin (207) for binding to the cytosolic TCDD receptor.…”

Section: Marine-derived Streptomyces Sp Mei02-81mentioning

confidence: 99%