Nitropeptin, a new dipeptide antibiotic possessing a nitro group.

Ohba, Kazunori; Nakayama, Hiroshi; Furihata, Kazuo; Shimazu, Akira; Endo, T.; Seto, Haruo; Ōtake, Noboru

doi:10.7164/antibiotics.40.709

Cited by 8 publications

(8 citation statements)

References 8 publications

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“…S . xanthochromogenes are also known to produce diverse array of chemical compounds such as Diastereoisomeric I-Na, Nitropeptin, xanthicin (I), Pravastatin, reductiomycin, alkaloid AM-6201 (Arishima et al, 1956; Onda et al, 1982; Ohba et al, 1987; Otake et al, 1988; Cho et al, 1993; Zhang et al, 2008). Eleven compounds having same molecular formula have been reported from S. levis .…”

Section: Discussionmentioning

confidence: 99%

Isolation, Screening, and Identification of Novel Isolates of Actinomycetes from India for Antimicrobial Applications

et al. 2016

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The search for novel bioactive compounds from the natural environment has rapidly been gaining momentum with the increase in multi-drug resistant (MDR) pathogens. In the present study, the antimicrobial potential of novel actinomycetes has been evaluated by initial screening of six soil samples. Primary and secondary screening was performed against Bacillus subtilis, Staphylococcus aureus, Escherichia coli, Candida albicans, Candida tropicalis, Trichophyton rubrum, and other MDR bacterial and fungal test strains, thirteen active isolates were selected for further study. Microbial strains were identified on the basis of growth conditions and other biochemical characters. Five most active microbial strains were identified using 16S rRNA sequence homology and designated as Streptomyces xanthophaeus MTCC 11938, Streptomyces variabilis MTCC 12266, Streptomyces xanthochromogenes MTCC 11937, Streptomyces levis EU 124569, and Streptomyces sp. NCIM 5500. Four antibacterial and three antifungal compounds isolated from the above five isolates were purified and partially characterized using UV absorption and IR spectra. Two antibacterial metabolites, belong to chromone and peptide antibiotic, respectively. The antifungal compounds were found to be of non-polyene nature. In conclusion, we study the isolation of novel bacterial strains of actinomycetes for producing novel compounds having antibacterial and antifungal activities from the unexplored agro-ecological niches of India. Also, this study paves the way for further characterization of these isolates of Streptomyces sp. for their optimum utilization for antimicrobial purposes.

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Section: Discussionmentioning

confidence: 99%

Isolation, Screening, and Identification of Novel Isolates of Actinomycetes from India for Antimicrobial Applications

et al. 2016

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“…In fact, less than thirty such compounds were isolated till now and among them dipeptide nitropeptine 13, isolated from S. xanthochromogenus, which displayed noticeable antifungal activity. [20] It would be reasonable to suppose that the unique biological activity of hormaomycin is connected with its nitro-group containing fragments. 3-(trans-2′-Nitrocyclopropyl)alanine itself (at least as a mixture of all possible isomers) was already tested and appeared to be inactive, but the inactivity of this amino acid could be connected just with the low capability of many amino acids to permeate across cell wall in the absence of the special transport mechanism because of their low hydrophobicity.…”

Section: Methodsmentioning

confidence: 99%

“…Then the temperature was decreased to 85 °C, and stirring continued for an additional 4 h. After this, the reaction mixture was allowed to cool to 20 °C and was concentrated under reduced pressure at a temperature not higher than 35 °C to give a red solid, which was purified by column chromatography (silica gel, EtOAc/hexanes 1:4) to give 103 (0.517g, 49%, R f = 0.37) as a light tan solid and 109 (0.12 g, 11%, R f = 0.49) as a white solid. 3 ); (44), 589 (10), 545 (15), 445 (12), 428 (18), 375 (18), 315 (21), 262 (20) (obtained as it was described for (2S,1'R,2'R)-isomer) using EDC (0. The crude product obtained after usual aqueous work-up (GP 7) was finally purified by column chromatography (EtOAc/hexanes 1:3, R f = 0.33) to give 147 (0.133 g, 57%) as a turbid glass.…”

Section: -Chloro-1-hydroxypyrrole-2-carbonitrile (103) and 5-chloro-2...mentioning

confidence: 99%

Final Elucidation of the Absolute Configuration of Hormaomycin - Total Synthesis of Hormaomycin and Analogs

Zlatopolski¹

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“…Aliphatic nitro compounds are very rare in nature, in fact, less than thirty such compounds have been isolated till now, and among them is the dipeptide nitropeptine 11 isolated from S. xanthochromogenus, which displayed noticeable antifungal activity. [34] One might therefore be tempted to suppose that the unique biological activity of Hormaomycin would be connected with its nitro group containing fragments. 3-(trans-2'-Nitrocyclopropyl)alanine itself (at least as a mixture of all possible isomers) was already tested and turned out to be inactive, but this inactivity might be due to the low capability of many amino acids to permeate across cell walls in the absence of a special transport mechanism because of their low lipophilicity.…”

Section: Nhmentioning

confidence: 99%

“….05 (+),29.64 (-),29.69 (-),31.91 (-),34.56 (-),35.51 (-), 36.67 (-), 36.71 (+), 37.86 (+) 39.42 (+), 41.76, 42.11, 43.45, 44.57, 51.44 (+), 52.68 (+), 52.75 (-), 54.65 (+), 54.93 (+), 59.86 (+), 60.17 (+), 61.36 (+), , 66.56, 69.07 (+), 103.29 (+), 109.25 (+), 119.28, 121.63, 126.93 (+), 127.31 (+), 127.44 (+), 127.55 (+), 127.63 (+), 128.19 (+), 128.45 (+), 128.67 (+), 141.68 (Cquat), 141.97 (Cquat), 159.14 (Cquat), 168.72 (Cquat), 168.92 (Cquat), 170.07 (Cquat), 170.68 (Cquat), 171.21 (Cquat), 171.69 (Cquat), 172.65 (Cquat); HRMS: M+H + calculated 1175.48021 measured 1175.47956; M+NH 4  + calculated 1192.50676 measured 1192.50686; M+Na + calculated 1197.46216 measured 1197.46120.…”

mentioning

confidence: 99%

Total Synthesis of Various Hormaomycin Analogues with Modified Amino Acid Residues

Raev¹

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AM 250 (250 MHz), Varian Unity 300 (300 MHz), Inova 500 (500 MHz), Inova 600 (600 MHz). 1 H chemical shifts are reported in ppm relative to residual peaks of deuterated solvents: δ (ppm) = 2.49 for [D 5 ]DMSO, 4.65 for HOD in D 2 O, 7.26 for CHCl 3 , 1.73 and 3.55 for [D 7 ]THF, 3.35 for CHD 2 OD. Higher-order NMR spectra were approximately interpreted as first-order spectra, if possible. For the characterization of the observed signal multiplicities the following abbreviations have been applied: s = singlet, d = doublet, t = triplet, q = quartet, quin = quintet, m = multiplet, as well as b = broad. 13 C NMR [additional DEPT (Distortionless Enhancement by Polarization Transfer) or APT (Attached Proton Test)]: Bruker AM 250 (62.9 MHz), AMX 300 (75.5 MHz) or Varian Unity 300 (75.5 MHz), Inova 500 (125.7 MHz), Inova 600 (125.7 MHz) instruments. 13 BORWIN HSS-2000, column Nucleodur ® C18 (250 mm × 20 mm, 5 µm, 100 Å), flow rate 18.0 ml/min. Optical rotations: Perkin-Elmer 241 digital polarimeter, 1-dm cell; optical rotation values are given in 10 -1 deg cm 2 g -1 ; concentrations (c) are given in g/100 mL. M.p.: Büchi 510 capillary melting point apparatus, uncorrected values. TLC: Macherey-Nagel pre-coated sheets, 0.25 mm Sil G/UV254. The chromatograms were viewed under UV light and/or by treatment with phosphomolybdic acid (10% in ethanol), or ninhydrine (0.2% in ethanol), or I 2 vapor. Column chromatography: Merck silica gel, grade 60, 230-400 mesh and Baker silica gel, 40-140 mesh. Elemental analyses: Mikroanalytisches Laboratorium des Instituts für Organische und Biomolekulare Chemie der Universität Göttingen.Starting materials: Anhydrous solvents were prepared according to standard methods by distillation over drying agents and were stored under nitrogen. All other solvents were distilled before use.All reactions were carried out with magnetic stirring and, when employing air-or moisturesensitive materials, in flame-dried glassware under argon or nitrogen. 7.General synthetic protocols Deprotection of N-Fmoc-protected peptides (GP 1)The respective protected peptide (1 mmol) was taken up with acetonitrile or THF (2 mL), diethylamine (2 mL) was added, and the resulting mixture left at ambient temperature for 40 min. All volatiles were evaporated under reduced pressure, the residue was taken up with toluene (2 × 5 mL), which was evaporated under reduced pressure to remove the last traces of diethylamine. The obtained crude N-deprotected peptide was directly used in the next condensation step. Peptide condensation step for the preparation of peptides using EDC/HOAt -mediated coupling (GP 2)EDC (1.03 mmol) and HOAt (1.05 mmol) were added to a cooled (4 °C) solution of the respective N-protected amino acid (1 mmol) in anhydrous CH 2 Cl 2 (3 mL). After 20 min, the solution of the appropriate crude N-deprotected peptide (0.97 mmol) and TMP (3 mmol) in

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Nitropeptin, a new dipeptide antibiotic possessing a nitro group.

Cited by 8 publications

References 8 publications

Isolation, Screening, and Identification of Novel Isolates of Actinomycetes from India for Antimicrobial Applications

Isolation, Screening, and Identification of Novel Isolates of Actinomycetes from India for Antimicrobial Applications

Final Elucidation of the Absolute Configuration of Hormaomycin - Total Synthesis of Hormaomycin and Analogs

Total Synthesis of Various Hormaomycin Analogues with Modified Amino Acid Residues

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