Liposidomycins: Novel nucleoside antibiotics which inhibit bacterial peptidoglycan synthesis.

Isono, Kiyoshi; Uramoto, Masakazu; Kusakabe, Hiroo; Kimura, Ken‐ichi; Izaki, Kazuo; Nelson, Chad; McCloskey, James A.

doi:10.7164/antibiotics.38.1617

Cited by 130 publications

(69 citation statements)

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“…8, 67) were isolated from a culture broth of the Actinomycete strain Streptomyces sp. MK730-62F2 in 2003 [111][112][113][114] and represent the newest members of a class of naturally occurring 6Ј-N-alkyl-5Ј-b-O-aminoribosyl-glycyluridine antibiotics including liposidomycins [115][116][117][118][119][120][121][122] (LPMs, 68), which have been shown to exhibit excellent antimicrobial activity against Gram-positive bacteria. In particular, the CPZs have shown excellent anti-mycobacterial activity in vitro against drug-susceptible (MICϭ3.13 mg/ml) and multi drug-resistant Mycobacterium tuberculosis strains (MICϭ3.13 mg/ml), and exhibit no significant toxicity in mice.…”

Section: -110)mentioning

confidence: 99%

Fine Synthetic Nucleoside Chemistry Based on Nucleoside Natural Products Synthesis

Ichikawa

2008

CHEMICAL & PHARMACEUTICAL BULLETIN

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Synthetic nucleoside chemistry based on nucleoside natural products synthesis were described. First, a samarium diiodide (SmI 2 )-promoted aldol reaction with the use of a a-phenylthioketone as an enolate was developed. The characteristics of this reaction are that the enolate can be regioselectively generated and the aldol reaction proceeds under near neutral condition. This reaction is proved to be a powerful reaction for the synthesis of complex nucleoside natural products, and herbicidin B and fully protected tunicaminyluracil, which were undecose nucleoside natural products, were synthesized. Next, the synthetic methodology of the caprazamycins, which are promising antibacterial nucleoside natural products, was also developed by the strategy including b bselective ribosylation without using a neighboring group participation. Our synthetic route provided a range of key analogues with partial structures to define the pharmacophore. Simplification of the caprazamycins was further pursued to develop diketopiperazine analogs.

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Section: -110)mentioning

confidence: 99%

Fine Synthetic Nucleoside Chemistry Based on Nucleoside Natural Products Synthesis

Ichikawa

2008

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…A-90289 A exhibited antimicrobial activities against clinically significant Gram-positive bacteria. As A-90289 A shows nearly the same translocase I inhibitory activity as A-90289 B, it is expected that A-90289 B possesses an equal antimicrobial potential because the fatty acid analogs of liposidomycin and muraminomicin were reported to have equal antimicrobial activities, 16,19,20 and the difference of the fatty acid moieties seemed to have no influence on the antibacterial activities. Therefore, not only muraminomicins and A-97065s, but also A-90289 A and B might be candidates for new antibacterial agents.…”

Section: Biological Properties Of A-90289 a And Bmentioning

confidence: 99%

A-90289 A and B, new inhibitors of bacterial translocase I, produced by Streptomyces sp. SANK 60405

et al. 2011

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During the course of screening for translocase I inhibitors, the new liposidomycin-related compounds, A-90289 A and B, were isolated from a culture broth of Streptomyces sp. SANK 60405. The structural elucidations were carried out by NMR and high-resolution mass spectral analyses, and they were classified as members of the liponucleoside antibiotics group with a sulfate group at the C-2¢ position. A-90289 A and B inhibited bacterial translocase I with IC 50 values of 36.5 ng ml À1 and 33.8 ng ml À1 , respectively.

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“…plant host interaction in Sinorhizobium meliloti (2) and virulence in Mycobacterium tuberculosis (3). Several sulfated bioactive compounds were isolated from microorganisms over the last decades, including the micafungin precursor FK463, (4), the cyanobacterial toxin cylindrospermopsin (5), and the liponucleoside antibiotic liposidomycins (6). However, in bacterial secondary metabolism, only few sulfotransferases have been studied in vitro.…”

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A New Arylsulfate Sulfotransferase Involved in Liponucleoside Antibiotic Biosynthesis in Streptomycetes

Kaysser

Eitel²,

Tanino³

et al. 2010

Journal of Biological Chemistry

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The Cpz4 reaction proceeds by a ping pong bi-bi mechanism. Several structural analogs of intermediates of the caprazamycin biosynthetic pathway were synthesized and tested as substrates of Cpz4. Des-N-methyl-acyl-caprazol was converted with highest efficiency 100 times faster than phenol. The fatty acyl side chain and the uridyl moiety seem to be important for substrate recognition by Cpz4. Liponucleosides, partially purified from various mutant strains, were readily sulfated by Cpz4 using p-nitrophenol sulfate. No product formation could be observed with PAPS as the donor substrate. Sequence homology of Cpz4 to the previously examined ASSTs is low. However, numerous orthologs are encoded in microbial genomes and represent interesting subjects for future investigations.

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Liposidomycins: Novel nucleoside antibiotics which inhibit bacterial peptidoglycan synthesis.

Cited by 130 publications

References 1 publication

Fine Synthetic Nucleoside Chemistry Based on Nucleoside Natural Products Synthesis

Fine Synthetic Nucleoside Chemistry Based on Nucleoside Natural Products Synthesis

A-90289 A and B, new inhibitors of bacterial translocase I, produced by Streptomyces sp. SANK 60405

A New Arylsulfate Sulfotransferase Involved in Liponucleoside Antibiotic Biosynthesis in Streptomycetes

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