Caprazamycin B, a Novel Anti-tuberculosis Antibiotic, from Streptomyces sp.

Igarashi, Masayuki; Nakagawa, Naoko; Doi, Norio; Hattori, Shigehiko; Naganawa, Hiroshi; Hamada, Masa

doi:10.7164/antibiotics.56.580

Cited by 153 publications

(84 citation statements)

References 2 publications

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“…Filtration followed by concentration in vacuo gave a residue, which was thoroughly washed with acetone to give 14 (74.7 mg, 99%) as a colorless solid. An analytical sample (prism) was prepared by crystallization from MeOH -H 2 X-Ray Crystallographic Analysis of 13 A colorless prism crystal described for 13, having approximate dimensions of 0.02ϫ0.18ϫ0.40 mm was chosen for X-ray crystallography. 3 .…”

Section: Caprazol (14)mentioning

confidence: 99%

Caprazamycins, Novel Lipo-nucleoside Antibiotics, from Streptomyces sp.

et al. 2005

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Novel antibiotics, active against acid-fast bacteria, caprazamycins, were isolated from the culture broth of Streptomyces sp. MK730-62F2. The planar structures of the compounds were determined by 2D NMR spectroscopic study. Furthermore, the absolute structure of caprazamycin B (2) was established by NMR spectroscopy and X-ray crystallography of its degradation products and by total synthesis of the 5-amino-5-deoxy-D-ribose moiety. In the course of degradation studies of 2 under alkaline and acidic conditions, we obtained the two core components, caprazene (11) and caprazol (14), respectively, in high yield.Structurally, caprazamycins belong to a family of lipouridyl antibiotics, which have been discovered as specific inhibitors of a bacterial translocase.

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Section: Caprazol (14)mentioning

confidence: 99%

Caprazamycins, Novel Lipo-nucleoside Antibiotics, from Streptomyces sp.

et al. 2005

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“…Subsequent polyethylene glycol-mediated protoplast transformation was performed as described by Kieser et al (20). Kanamycin resistance mutants were selected and designated as S. coelicolor M512/cpzLK09 (1)(2)(3).…”

Section: Methodsmentioning

confidence: 99%

Identification and Manipulation of the Caprazamycin Gene Cluster Lead to New Simplified Liponucleoside Antibiotics and Give Insights into the Biosynthetic Pathway

Kaysser

Lutsch

Siebenberg

et al. 2009

Journal of Biological Chemistry

127

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“…To date, a variety of nucleoside antibiotics have been reported as translocase I inhibitors, 5 such as mureidomycins, 6 pacidamycins, 7 napsamycins, 8 liposidomycins, 9 tunicamycin, 10 capuramycins, 11-17 muraymycins 18 and caprazamycins. 19,20 In contrast, only a few inhibitors have been reported for the steps of UDP-MurNAc-pentapeptide formation. D-cycloserine and O-carbamyl-D-serine are known inhibitors for D-Ala-D-Ala pathways Alr and Ddl, [21][22][23] and recently a few synthetic compounds were reported as MurF inhibitors.…”

Section: Introductionmentioning

confidence: 99%

A novel assay of bacterial peptidoglycan synthesis for natural product screening

et al. 2009

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Although a large number of microbial metabolites have been discovered as inhibitors of bacterial peptidoglycan biosynthesis, only a few inhibitors were reported for the pathway of UDP-MurNAc-pentapeptide formation, partly because of the lack of assays appropriate for natural product screening. Among the pathway enzymes, D-Ala racemase (Alr), D-Ala:D-Ala ligase (Ddl) and UDPMurNAc-tripeptide:D-Ala-D-Ala transferase (MurF) are particularly attractive as antibacterial targets, because these enzymes are essential for growth and utilize low-molecular-weight substrates. Using dansylated UDP-MurNAc-tripeptide and L-Ala as the substrates, we established a cell-free assay to measure the sequential reactions of Alr, Ddl and MurF coupled with translocase I. This assay is sensitive and robust enough to screen mixtures of microbial metabolites, and enables us to distinguish the inhibitors for D-Ala-D-Ala formation, MurF and translocase I. D-cycloserine, the D-Ala-D-Ala pathway inhibitor, was successfully detected by this assay (IC 50 ¼1.7 lg ml À1 ). In a large-scale screening of natural products, we have identified inhibitors for D-Ala-D-Ala synthesis pathway, MurF and translocase I.

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Caprazamycin B, a Novel Anti-tuberculosis Antibiotic, from Streptomyces sp.

Cited by 153 publications

References 2 publications

Caprazamycins, Novel Lipo-nucleoside Antibiotics, from Streptomyces sp.

Caprazamycins, Novel Lipo-nucleoside Antibiotics, from Streptomyces sp.

Identification and Manipulation of the Caprazamycin Gene Cluster Lead to New Simplified Liponucleoside Antibiotics and Give Insights into the Biosynthetic Pathway

A novel assay of bacterial peptidoglycan synthesis for natural product screening

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