The Structures of Sulfomycins II and III.

Kohno, Jun; Kameda, Noriaki; Nishio, Maki; Kinumaki, Akio; Komatsubara, Saburo

doi:10.7164/antibiotics.49.1063

Cited by 22 publications

(16 citation statements)

References 7 publications

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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: 70%

“…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%

See 1 more Smart Citation

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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Section: Trisubstituted Pyridinesmentioning

confidence: 70%

Section: Piperidines and Dehydropiperidinesmentioning

confidence: 99%

Pharmacologically Active Sulfur-Containing Compounds

Řezanka¹,

Sobotka²,

Spížek³

et al. 2006

AIAMC

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“…Sulfomycins I-III (67-69) were first isolated by Egawa et al from Streptomyces viridochromogenes MCRL-0368 ( Figure 27) [88]. These compounds exhibited antibacterial activity against Gram-positive cocci, bacilli, mycoplasma, and anaerobic bacteria, as well as against those resistant to penicillin, streptomycin, tetracycline, chloramphenicol, and staphylococci freshly isolated from clinical material [88,89]. They are weakly active against Neisseria, Bordetella, and mycobacteria.…”

Section: Sulfomycins I-iiimentioning

confidence: 99%

“…They all contain two thiazole rings, three oxazole rings, four dehydroalanines, Thr and pyridine, and differ only in one of the oxazole units [89,90]. In the structure of 68, the Thr unit has an L-configuration [89]. Regarding the carbon atom attached to the methoxy group, no stereochemical information was provided.…”

Section: Sulfomycins I-iiimentioning

confidence: 99%

Naturally Occurring Oxazole-Containing Peptides

et al. 2020

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“…The thiostrepton family of compounds 60 (Dutcher and Vandeputte 1955 ; Anderson et al 1970 ; Bond et al 2001 ; Nishimura et al 1959 ; Mori et al 2007 ; Tori et al 1981 ; Miyairi et al 1970 ; Hensens and Albers-Schönberg 1983 , 1978 ; Puar et al 1981 ) and closely related Sch 40832 61 (Puar et al 1998 ) contain the thiazoline-(Z)-dehydrobutyrine residue, in which the heterocyclic ring is not fully dehydrated. Furthermore, oxazole- and 5-methyl-oxazole-dehydroamino acids such as oxazole-dehydroalanine, 5-methyl-oxazole-dehydroalanine, oxazole-dehydrobutyrine, 5-methyl-oxazole-dehydrobutyrine, oxazole-dehydrohomobutyrine, 5-methyl-oxazole-dehydrohomobutyrine, oxazole-dehydroleucine, and 5-methyl-oxazole-dehydrohomoserine were found in geninthiocin 62 (Yun et al 1994a , b , c ), berninamycins (Liesch and Rinehart 1977 ; Abe et al 1988 ; Kodani and Ninomiya 2013 ), sulfomycins 63 (Egawa et al 1969 ; Kohno et al 1996 ; Vijaya Kumar et al 1999 ), promoinducin (Yun and Seto 1995 ), thiotipin (Yun et al 1994a , b , c ), A10255 64 (Boeck et al 1992 ; Debono et al 1992 ; Favret et al 1992 ), tioaxamycin (Yun et al 1994a , b , c ), radamycin (Castro Rodríguez et al 2002 ), and TP-1161 (Engelhardt et al 2010 ). Oxazole-dehydroalanine and oxazole-dehydrobutyrine were also found, respectively, in mechercharmycin A 65 (IB-01211) (Kanoh et al 2005 ; Hernández et al 2007a , b ) [226–228] and urukthapelstatin A (Matsuo et al 2007 ), a new class of thiopeptides of antitumour activity, which does not have six-membered heterocyclic moiety.…”

Section: Introductionmentioning

confidence: 99%

α,β-Dehydroamino acids in naturally occurring peptides

Siodłak

2014

Amino Acids

119

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α,β-Dehydroamino acids are naturally occurring non-coded amino acids, found primarily in peptides. The review focuses on the type of α,β-dehydroamino acids, the structure of dehydropeptides, the source of their origin and bioactivity. Dehydropeptides are isolated primarily from bacteria and less often from fungi, marine invertebrates or even higher plants. They reveal mainly antibiotic, antifungal, antitumour, and phytotoxic activity. More than 60 different structures were classified, which often cover broad families of peptides. 37 different structural units containing the α,β-dehydroamino acid residues were shown including various side chains, Z and E isomers, and main modifications: methylation of peptide bond as well as the introduction of ester group and heterocycle ring. The collected data show the relation between the structure and bioactivity. This allows the activity of compounds, which were not studied in this field, but which belong to a larger peptide family to be predicted. A few examples show that the type of the geometrical isomer of the α,β-dehydroamino acid residue can be important or even crucial for biological activity.Electronic supplementary materialThe online version of this article (doi:10.1007/s00726-014-1846-4) contains supplementary material, which is available to authorized users.

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The Structures of Sulfomycins II and III.

Cited by 22 publications

References 7 publications

Pharmacologically Active Sulfur-Containing Compounds

Pharmacologically Active Sulfur-Containing Compounds

Naturally Occurring Oxazole-Containing Peptides

α,β-Dehydroamino acids in naturally occurring peptides

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