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Katsumi Kakinuma – One of the best experts on this subject based on the ideXlab platform.

  • Biosynthesis of 2-Deoxystreptamine-containing Antibiotics in Streptoalloteichus hindustanus JCM 3268: Characterization of 2-Deoxy-scyllo-inosose Synthase
    The Journal of Antibiotics, 2006
    Co-Authors: Toshifumi Hirayama, Katsumi Kakinuma, Fumitaka Kudo, Hideyuki Tamegai, Kazumasa Kojima, Tadashi Eguchi


    A part of the new biosynthetic gene cluster for 2-Deoxystreptamine-containing antibiotics was identified from Streptoalloteichus hindustanus . The alloH gene in the gene cluster was deduced to encode 2-deoxy- scyllo -inosose synthase and the expressed protein AlloH was confirmed to have this enzyme activity. Furthermore, biochemical properties of AlloH were studied.

  • Extended Sequence and Functional Analysis of the Butirosin Biosynthetic Gene Cluster in Bacillus circulans SANK 72073
    The Journal of Antibiotics, 2005
    Co-Authors: Fumitaka Kudo, Mario Numakura, Hideyuki Tamegai, Hideki Yamamoto, Tadashi Eguchi, Katsumi Kakinuma


    Butirosin produced by Bacillus circulans is among the clinically important 2-Deoxystreptamine containing aminoglycoside antibiotics and its unique structure is found in ( S )-4-amino-2-hydroxyburyric acid substituted at C-1 of 2-Deoxystreptamine. Recently, the key part of the butirosin biosynthetic gene cluster has been identified from Bacillus circulans SANK 72073, however the whole gene for the biosynthesis awaited for identification. In the present study, we undertook extended analysis of the butirosin biosynthetic gene cluster and found nine additional open reading flames (ORFs), btrQ , btrR1 , btrR2 , btrT , btrU , btrV , btrW , btrX and orf1 in the cluster. In addition, we constructed disruption mutants of btrR1 and btrP-V , and found that the btr genes ( ca. 24 Kb) between btrR1 and btrP-V are at least required for the butirosin biosynthesis.

  • Stereochemical recognition of doubly functional aminotransferase in 2-Deoxystreptamine biosynthesis
    Journal of the American Chemical Society, 2005
    Co-Authors: Kenichi Yokoyama, Fumitaka Kudo, Hideyuki Tamegai, Tadashi Eguchi, Mieko Kuwahara, Kousuke Inomata, Katsumi Kakinuma


    The doubly functional aminotransferase BtrS in the 2-Deoxystreptamine (DOS) biosynthesis, in which two transaminations are involved, was characterized by a genetic as well as a chemical approach with the heterologously expressed enzyme. The gene disruption study clearly showed that BtrS is involved, in addition to the previously confirmed first transamination, in the second transamination as well. This dual function of BtrS for the DOS biosynthesis was further confirmed by the structural determination of the reverse reaction product from DOS. Enantiospecific formation of the reverse reaction product from DOS clearly showed that BtrS distinguishes the enantiotopic amino groups of DOS, but in contrast, both enantiomers of 2-deoxy-scyllo-inosose (DOI) were efficiently accepted by BtrS to give a racemic product. This unique stereochemical recognition of DOI chirality and DOS prochirality by BtrS is mechanistically explained by a specific hydrogen-bond donating force in the enzyme active site as a particular f…

Jae Kyung Sohng – One of the best experts on this subject based on the ideXlab platform.

  • Re-engineering of genetic circuit for 2-Deoxystreptamine (2-DOS) biosynthesis in Escherichia coli BL21 (DE3)
    Biotechnology Letters, 2013
    Co-Authors: Amit Kumar Chaudhary, Je Won Park, Yeo Joon Yoon, Byung-gee Kim, Jae Kyung Sohng


    Various approaches for monocistronic constructions of genetic circuits have been designed for metabolite production but there has been no attempt to apply such methodology for aminoglycosides biosynthesis. Here, a simple and commercially available bio-part, despite the current trend focusing on the standardized BioBricks bio-parts available in the registry, is used. A 181-bp nucleotide fragment was designed for the efficient construction of an expression vector for monocistronic assembly of genes. Furthermore, a single vector with multi-monocistronic assembled genes for 2-Deoxystreptamine (2-DOS) synthesis was constructed for production in engineered Escherichia coli. The working efficiency of model vector was concluded by reporter assay whereas the expressions of biosynthesis genes were confirmed by RT-PCR and SDS-PAGE. Production of 2-DOS was confirmed by TLC, LC-ELSD, and ESI–MS/MS.

  • Biosynthetic approach for the production of new aminoglycoside derivative.
    Journal of bioscience and bioengineering, 2010
    Co-Authors: Keshav Kumar Nepal, Jin Cheol Yoo, Jae Kyung Sohng


    Aminoglycoside antibiotics can be classified into two major groups; streptamine containing and 2-Deoxystreptamine containing antibiotics. Here, we report a biosynthetic approach for the fusion of spectinomycin and kanamycin biosynthetic gene clusters to yield the new aminoglycoside derivative, oxykanamycinC, in a non-aminoglycoside producing heterologous host.

  • Heterologous production of paromamine in Streptomyces lividans TK24 using kanamycin biosynthetic genes from Streptomyces kanamyceticus ATCC12853
    Molecules and Cells, 2009
    Co-Authors: Keshav Kumar Nepal, Jae Kyung Sohng


    The 2-Deoxystreptamine and paromamine are two key intermediates in kanamycin biosynthesis. In the present study, pSK-2 and pSK-7 recombinant plasmids were constructed with two combinations of genes: kan ABK and kan ABKF and kac A respectively from kanamycin producer Streptomyces kanamyceticus ATCC12853. These plasmids were heterologously expressed into Streptomyces lividans TK24 independently and generated two recombinant strains named S. lividans Sk-2/SL and S. lividans SK-7/SL, respectively. ESI/ MS and ESI-LC/MS analysis of the metabolite from S. lividans SK-2/SL showed that the compound had a molecular mass of 163 [M + H]^+, which corresponds to that of 2-Deoxystreptamine. ESI/MS and MS/MS analysis of metabolites from S. lividans SK-7/SL demonstrated the production of paromamine with a molecular mass of 324 [M + H]^+. In this study, we report the production of paromamine in a heterologous host for the first time. This study will evoke to explore complete biosynthetic pathways of kanamycin and related aminoglycoside antibiotics.

Floris L. Van Delft – One of the best experts on this subject based on the ideXlab platform.

  • 2-Deoxystreptamine Conjugates by Truncation-Derivatization of Neomycin.
    Pharmaceuticals (Basel Switzerland), 2010
    Co-Authors: M. Waqar Aslam, Floris P. J. T. Rutjes, Leandro C. Tabares, Alessio Andreoni, Gerard W. Canters, Floris L. Van Delft


    A small library of truncated neomycin-conjugates is prepared by consecutive removal of 2,6-diaminoglucose rings, oxidation-reductive amination of ribose, oxidation-conjugation of aminopyridine/aminoquinoline and finally dimerization. The dimeric conjugates were evaluated for antibacterial activity with a unique hemocyanin-based biosensor. Based on the outcome of these results, a second-generation set of monomeric conjugates was prepared and found to display significant antibacterial activity, in particular with respect to kanamycin-resistant E. coli.

  • Fully orthogonally protected 2-Deoxystreptamine from kanamycin.
    The Journal of organic chemistry, 2008
    Co-Authors: M. Waqar Aslam, Guuske Frederike Busscher, René De Gelder, Floris P. J. T. Rutjes, David P. Weiner, Floris L. Van Delft


    A fully orthogonally protected and enantiopure 2-Deoxystreptamine derivative is prepared in a few straightforward steps from commercially available kanamycin. Resolution of a sterically hindered diacetate was effected by a Verenium esterase and was followed by a chemoselective Staudinger reduction−acylation protocol.

  • A short and scalable route to orthogonally O-protected 2-Deoxystreptamine.
    The Journal of organic chemistry, 2007
    Co-Authors: Sebastiaan A. M. W. Van Den Broek, Floris L. Van Delft, Floris P. J. T. Rutjes, Bas W. T. Gruijters, Richard H. Blaauw


    A seven-step synthesis of orthogonally O-protected 2-deoxy-streptamine has been developed from readily available neomycin, with an overall yield of 28%. Key chemical transformations include a chemoselective glycosidic bond hydrolysis and two regioselective protective group manipulations involving acetylation and deacetylation. The synthetic route is amenable to scale-up for the production of multigram quantities of enantiopure and orthogonally O-protected 2-Deoxystreptamine, a versatile scaffold for the generation of libraries of RNA-targeting ligands.