A new aminoglycoside antibiotic, sannamycin C and its 4-N-glycyl derivative.

Deushi, Takeo; Yamaguchi, Takashi; Kamiya, Kazuhiro; Iwasaki, Akio; Mizoguchi, Toshimi; Nakayama, Masahito; Watanabe, Isamu; Itoh, Hisakatsu; Mori, Toshihito

doi:10.7164/antibiotics.33.1274

Cited by 14 publications

(6 citation statements)

References 4 publications

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“…For example, the genus Streptomyces accounts for about 80% of all natural products recovered from actinomycetes to date [34]. As one example, Streptomyces sannanensis produces new aminoglycoside antibiotics sannamycins A, B and C with potent activities against Gram-positive bacteria [35]. First organic chemistry analyses of the novel isolate RV15 points to entirely novel cyclic peptides which are currently being characterized further.…”

Section: Resultsmentioning

confidence: 99%

Isolation, Phylogenetic Analysis and Anti-infective Activity Screening of Marine Sponge-Associated Actinomycetes

et al. 2010

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Terrestrial actinomycetes are noteworthy producers of a multitude of antibiotics, however the marine representatives are much less studied in this regard. In this study, 90 actinomycetes were isolated from 11 different species of marine sponges that had been collected from offshore Ras Mohamed (Egypt) and from Rovinj (Croatia). Phylogenetic characterization of the isolates based on 16S rRNA gene sequencing supported their assignment to 18 different actinomycete genera representing seven different suborders. Fourteen putatively novel species were identified based on sequence similarity values below 98.2% to other strains in the NCBI database. A putative new genus related to Rubrobacter was isolated on M1 agar that had been amended with sponge extract, thus highlighting the need for innovative cultivation protocols. Testing for anti-infective activities was performed against clinically relevant, Gram-positive (Enterococcus faecalis, Staphylococcus aureus) and Gram-negative (Escherichia coli, Pseudomonas aeruginosa) bacteria, fungi (Candida albicans) and human parasites (Leishmania major, Trypanosoma brucei). Bioactivities against these pathogens were documented for 10 actinomycete isolates. These results show a high diversity of actinomycetes associated with marine sponges as well as highlight their potential to produce anti-infective agents.

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Section: Resultsmentioning

confidence: 99%

Isolation, Phylogenetic Analysis and Anti-infective Activity Screening of Marine Sponge-Associated Actinomycetes

et al. 2010

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“…Reaction of 0.27 mol of 11 with 7.5 mmol of base in pure acetonitrile under careful exclusion of moisture (dry box) yields after crystallization 93% rac-13a [ The structures rac-13a -f are substantiated by fully analyzed 'H-NMR spectra ( First information about the regiochemistry of epoxide opening in the tricycles 13 came from the reaction of rac13a with sodium azide (excess NaN3, MgS04, methanol, reflux) (Scheme 4). Continuous monitoring of the reaction progress (TLC, 'H NMR) reveals only one product, which can be isolated after total conversion and crystallization with at least 95% yield and is identified as 14a 2p,3f5,4~(,6P I ent-1 ent-20a ent-20b 1733 the le,4a,6e (17**) conformation in the equilibrium with the la,4e,6a conformation (17*) is confirmd i. a. by the generally large coupling constants 558.6 (9.5-12.0 Hz) and 56.1 (7.5 -11.2 Hz) and the long range coupling constants J3,5rr (1)(2)(3). Accordingly, the signals of equatorial 5a-H generally appear at lower field than those of axial 5P-H. After hydrolysis of the carbamate ring in 17alent-17a and 17clent-17c [water/methanol, Ba(OH2)] and acidification with conc.…”

Section: Bausteinementioning

confidence: 91%

Aminoglycoside antibiotics — Enantiomerically pure sannamine building blocks

et al. 1989

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Starting from the prochiral dianhydrodeoxy-epi-inositol 9 a highly efficient synthesis for rac-sannamines (1, salts, derivatives) and rue-de-0-methylsannamine (18, salt) has been developed. Key steps are two regiospecific, practically quantitative epoxide opening reactions: intramolecularly in the diepoxyurethanes 11 and intermolecularly in the epoxyurethanes roc-13. With (R)-1 -phenylethylamine as potential primary amino group in the second step separation of the corresponding diastereomers (16,16') is achieved without significant loss of material. By this route enantiomerically pure (de-0-methy1)sannamines become available in which all functionalities are protected except that to be glycosidated. Attempts for an asymmetric realization of this synthesis resulted in only very small ee(de) values.Sannamine (1) (2-deoxyfortamine) and sporamine (2) are the aglycon building blocks') of a new class of aminoglycoside antibiotics (sannamycins*), istamycins3', sporaricins4'). Their structure is closely related to fortamine (3), the aglycon component of the fortimicins (astromicins)". Reduced side effects and activity towards resistent strains of bacteria are characteristic of this group of antibiotics. A pecularity is their relatively simple pseudo disaccharide structure -with only one sugar (purpurosamine) and one non-sugar component, making synthetic activities in this area particularly attractive. (-1-3In recent years several total syntheses for the aglyca 1 -3 (in brackets antibiotics numbering) starting from racemic o r chiral material were published6' -including the detailed protocol of our own access to enantiomerically pure (de-0-methy1)fortamines". The paper presented here summarizes our activities in the sannamine area'), the subsequent paper*' the results of a n investigation in the sporamine

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“…82 "C (from EtOH) (Found: C,54.0;H,4.4;N,14.3. C27H28N6010 requires C,54.36;H,4.73; N, 14.08%); R, 0.28 [ethyl acetate-cyclohexane (2 : l)]; v,,,(KBr)/cm -' 3 3 4 0 ~ (NH), 2 9 2 0 ~ (CH) and 1590s (N=O); dH(CDC13) 9.10 (2 H, d, 2 x DNP 3-H), 8.67 (1 H,d,8.20 (2 H,dd,2 x DNP 5-H), 7.20 ( 5 H,m,Ph),6.84 (2 H,d,2 x DNP 6-H), 3.70 (1 H,m,3.69 (3 H,s,OMe),3.31/3.00 (2 H,dd,), 1.96/1.79 (2 H, m, 3-H,), 1.94/1.34 (2 H, m, 4-H,) 4.89 (1 H, 9, 1'-H), 4.64 (1 H, d, 1-H), 3.74 (1 H, dddd, 5-H), (3 H, d, 2'-H3); J 1 , 2 3.5,JZ,NH 9 andJ,,,,,13.5;Gc(CDC13) (2.30 g, 4.60 mmol) in dry ethanol (100 cm3) was added NaBH, in portions (500 mg, 13.00 mmol) at room temperature within 4 h. Additional NaBH, (200 mg, 5.20 mmol) was added and the reaction mixture was stirred for 1 h ( -90% conversion, TLC control, Rf 6g 0.40, ethyl acetate).…”

Section: Methyl 2346-tetradeoxy-2-hydroxyimino-6-( Tr$uoroacetyl-[ ( ...mentioning

confidence: 99%

“…Compound 6k had [a];' +38 (c 0.08, CH,Cl,); vmaX-(KBr)/cm-' 3348w (NH), 3010w (CH) and 1586s (N=O); d~(CDc13) 9.15 (2 H, d, 2 x DNP 3-H), 8.88 (1 H,t,8.79 (1 H,d,8.31/8.21 (2 H,dd,2 x DNP 5-H), 6.96 (2 H, d, 2 x DNP 6-H), 4.90 (1 H, d, 1-H), 4.20 (1 H, dddd, 5-H) Compound ent-6k had [a];' -41 (c 0.16,CH,Cl,); 'H, 13C NMR, IR data are identical with those of isomer 6k.…”

Section: Methyl 2346-tetradeoxy-2-hydroxyimino-6-( Tr$uoroacetyl-[ ( ...mentioning

confidence: 99%

Total syntheses of enantiomerically pure D- and L-glycosyl donors as components of sannamycin-type aminoglycoside antibiotics

Ludin¹,

Schwesinger²,

Schwesinger³

et al. 1994

J. Chem. Soc., Perkin Trans. 1

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A new aminoglycoside antibiotic, sannamycin C and its 4-N-glycyl derivative.

Cited by 14 publications

References 4 publications

Isolation, Phylogenetic Analysis and Anti-infective Activity Screening of Marine Sponge-Associated Actinomycetes

Isolation, Phylogenetic Analysis and Anti-infective Activity Screening of Marine Sponge-Associated Actinomycetes

Aminoglycoside antibiotics — Enantiomerically pure sannamine building blocks

Total syntheses of enantiomerically pure D- and L-glycosyl donors as components of sannamycin-type aminoglycoside antibiotics

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