{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,7]],"date-time":"2026-10-07T18:15:25Z","timestamp":1791396925302,"version":"4.3.3"},"reference-count":31,"publisher":"Springer Science and Business Media LLC","issue":"1","license":[{"start":{"date-parts":[[2013,9,11]],"date-time":"2013-09-11T00:00:00Z","timestamp":1378857600000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/www.springer.com\/tdm"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["J Antibiot"],"published-print":{"date-parts":[[2014,1]]},"DOI":"10.1038\/ja.2013.88","type":"journal-article","created":{"date-parts":[[2013,9,11]],"date-time":"2013-09-11T06:15:17Z","timestamp":1378880117000},"page":"65-70","source":"Crossref","is-referenced-by-count":22,"title":["C-glycosylation of anhydrotetracycline scaffold with SsfS6 from the SF2575 biosynthetic pathway"],"prefix":"10.1038","volume":"67","author":[{"given":"Li","family":"Li","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Peng","family":"Wang","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yi","family":"Tang","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"297","published-online":{"date-parts":[[2013,9,11]]},"reference":[{"key":"BFja201388_CR1","doi-asserted-by":"publisher","first-page":"2141","DOI":"10.1021\/np040106y","volume":"67","author":"MS Butler","year":"2004","unstructured":"Butler, M. S. The role of natural product chemistry in drug discovery. J. Nat. Prod. 67, 2141\u20132153 (2004).","journal-title":"J. Nat. Prod."},{"key":"BFja201388_CR2","doi-asserted-by":"publisher","first-page":"1089","DOI":"10.1126\/science.1176667","volume":"325","author":"MA Fischbach","year":"2009","unstructured":"Fischbach, M. A. & Walsh, C. T. Antibiotics for emerging pathogens. Science 325, 1089\u20131093 (2009).","journal-title":"Science"},{"key":"BFja201388_CR3","doi-asserted-by":"publisher","first-page":"1811","DOI":"10.1039\/c1np00045d","volume":"28","author":"RW Gantt","year":"2011","unstructured":"Gantt, R. W., Peltier-Pain, P. & Thorson, J. S. Enzymatic methods for glyco(diversification\/randomization) of drugs and small molecules. Nat. Prod. Rep. 28, 1811\u20131853 (2011).","journal-title":"Nat. Prod. Rep."},{"key":"BFja201388_CR4","doi-asserted-by":"publisher","first-page":"1303","DOI":"10.2174\/0929867013372193","volume":"8","author":"V Kren","year":"2001","unstructured":"Kren, V. & Martinkova, L. Glycosides in medicine: \u201cThe role of glycosidic residue in biological activity\u201d. Curr. Med. Chem. 8, 1303\u20131328 (2001).","journal-title":"Curr. Med. Chem."},{"key":"BFja201388_CR5","doi-asserted-by":"publisher","first-page":"99","DOI":"10.1039\/np9971400099","volume":"14","author":"AC Weymouth-Wilson","year":"1997","unstructured":"Weymouth-Wilson, A. C. The role of carbohydrates in biologically active natural products. Nat. Prod. Rep. 14, 99\u2013110 (1997).","journal-title":"Nat. Prod. Rep."},{"key":"BFja201388_CR6","doi-asserted-by":"publisher","first-page":"1008","DOI":"10.1038\/nature05814","volume":"446","author":"CJ Thibodeaux","year":"2007","unstructured":"Thibodeaux, C. J., Melancon, C. E. & Liu, H. W. Unusual sugar biosynthesis and natural product glycodiversification. Nature 446, 1008\u20131016 (2007).","journal-title":"Nature"},{"key":"BFja201388_CR7","doi-asserted-by":"publisher","first-page":"571","DOI":"10.1073\/pnas.0408463102","volume":"102","author":"MA Fischbach","year":"2005","unstructured":"Fischbach, M. A., Lin, H., Liu, D. R. & Walsh, C. T. In vitro characterization of IroB, a pathogen-associated C-glycosyltransferase. Proc. Natl Acad. Sci. USA 102, 571\u2013576 (2005).","journal-title":"Proc. Natl Acad. Sci. USA"},{"key":"BFja201388_CR8","doi-asserted-by":"publisher","first-page":"1291","DOI":"10.1126\/science.1130028","volume":"313","author":"C Zhang","year":"2006","unstructured":"Zhang, C. et al. Exploiting the reversibility of natural product glycosyltransferase-catalyzed reactions. Science 313, 1291\u20131294 (2006).","journal-title":"Science"},{"key":"BFja201388_CR9","doi-asserted-by":"publisher","first-page":"405","DOI":"10.1021\/jm00340a014","volume":"6","author":"JL Spencer","year":"1963","unstructured":"Spencer, J. L., Hlavka, J. J., Petisi, J., Krazinski, H. M. & Boothe, J. H. 6-Deoxytetracyclines. V. 7,9-disubstituted products. J. Med. Chem. 6, 405\u2013407 (1963).","journal-title":"J. Med. Chem."},{"key":"BFja201388_CR10","doi-asserted-by":"publisher","first-page":"44","DOI":"10.1021\/jm00313a009","volume":"10","author":"MJ Martell Jr.","year":"1967","unstructured":"Martell, M. J. Jr. & Boothe, J. H. The 6-deoxytetracyclines. VII. Alkylated aminotetracyclines possessing unique antibacterial activity. J. Med. Chem. 10, 44\u201346 (1967).","journal-title":"J. Med. Chem."},{"key":"BFja201388_CR11","doi-asserted-by":"publisher","first-page":"400","DOI":"10.1016\/j.bmcl.2005.09.078","volume":"16","author":"PE Sum","year":"2006","unstructured":"Sum, P. E., Ross, A. T., Petersen, P. J. & Testa, R. T. Synthesis and antibacterial activity of 9-substituted minocycline derivatives. Bioorg. Med. Chem. Lett. 16, 400\u2013403 (2006).","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"BFja201388_CR12","doi-asserted-by":"publisher","first-page":"17677","DOI":"10.1021\/ja907852c","volume":"131","author":"LB Pickens","year":"2009","unstructured":"Pickens, L. B. et al. Biochemical analysis of the biosynthetic pathway of an anticancer tetracycline SF2575. J. Am. Chem. Soc. 131, 17677\u201317689 (2009).","journal-title":"J. Am. Chem. Soc."},{"key":"BFja201388_CR13","doi-asserted-by":"publisher","first-page":"320","DOI":"10.7164\/antibiotics.45.320","volume":"45","author":"M Hatsu","year":"1992","unstructured":"Hatsu, M. et al. A new tetracycline antibiotic with antitumor activity. I. Taxonomy and fermentation of the producing strain, isolation and characterization of SF2575. J. Antibiot. (Tokyo) 45, 320\u2013324 (1992).","journal-title":"J. Antibiot. (Tokyo)"},{"key":"BFja201388_CR14","doi-asserted-by":"publisher","first-page":"325","DOI":"10.7164\/antibiotics.45.325","volume":"45","author":"M Hatsu","year":"1992","unstructured":"Hatsu, M. et al. A new tetracycline antibiotic with antitumor activity. II. The structural elucidation of SF2575. J. Antibiot. (Tokyo) 45, 325\u2013330 (1992).","journal-title":"J. Antibiot. (Tokyo)"},{"key":"BFja201388_CR15","doi-asserted-by":"publisher","first-page":"2270","DOI":"10.1128\/AAC.37.11.2270","volume":"37","author":"RT Testa","year":"1993","unstructured":"Testa, R. T. et al. In vitro and in vivo antibacterial activities of the glycylcyclines, a new class of semisynthetic tetracyclines. Antimicrob. Agents Chemother. 37, 2270\u20132277 (1993).","journal-title":"Antimicrob. Agents Chemother."},{"key":"BFja201388_CR16","doi-asserted-by":"publisher","first-page":"11136","DOI":"10.1002\/anie.201205426","volume":"51","author":"P Wang","year":"2012","unstructured":"Wang, P., Kim, W., Pickens, L. B., Gao, X. & Tang, Y. Heterologous expression and manipulation of three tetracycline biosynthetic pathways. Angew. Chem. Int. Ed. 51, 11136\u201311140 (2012).","journal-title":"Angew. Chem. Int. Ed."},{"key":"BFja201388_CR17","doi-asserted-by":"publisher","first-page":"1277","DOI":"10.1002\/prot.24289","volume":"81","author":"F Wang","year":"2013","unstructured":"Wang, F. et al. Crystal structure of SsfS6, the putative C-glycosyltransferase involved in SF2575 biosynthesis. Proteins 81, 1277\u20131282 (2013).","journal-title":"Proteins"},{"key":"BFja201388_CR18","volume-title":"Practical Streptomyces Genetics.","author":"T Kieser","year":"2000","unstructured":"Kieser, T., Bibb, M., Buttner, M., Chater, K. & Hopwood, D. Practical Streptomyces Genetics., John Innes Foundation: Norwich, (2000)."},{"key":"BFja201388_CR19","doi-asserted-by":"publisher","first-page":"721","DOI":"10.1016\/S1074-5521(02)00154-0","volume":"9","author":"L Rodriguez","year":"2002","unstructured":"Rodriguez, L. et al. Engineering deoxysugar biosynthetic pathways from antibiotic-producing microorganisms. A tool to produce novel glycosylated bioactive compounds. Chem. Biol 9, 721\u2013729 (2002).","journal-title":"Chem. Biol"},{"key":"BFja201388_CR20","doi-asserted-by":"publisher","first-page":"1958","DOI":"10.1016\/j.carres.2010.07.004","volume":"345","author":"S Karki","year":"2010","unstructured":"Karki, S., Yoo, H. G., Kwon, S. Y., Suh, J. W. & Kwon, H. J. Cloning and in vitro characterization of dTDP-6-deoxy-l-talose biosynthetic genes from Kitasatospora kifunensis featuring the dTDP-6-deoxy-l-lyxo-4-hexulose reductase that synthesizes dTDP-6-deoxy-l-talose. Carbohydr. Res. 345, 1958\u20131962 (2010).","journal-title":"Carbohydr. Res."},{"key":"BFja201388_CR21","doi-asserted-by":"publisher","first-page":"423","DOI":"10.1038\/nchembio803","volume":"2","author":"K Watanabe","year":"2006","unstructured":"Watanabe, K. et al. Total biosynthesis of antitumor nonribosomal peptides in Escherichia coli. Nat. Chem. Biol. 2, 423\u2013428 (2006).","journal-title":"Nat. Chem. Biol."},{"key":"BFja201388_CR22","doi-asserted-by":"publisher","first-page":"959","DOI":"10.1016\/j.chembiol.2004.04.016","volume":"11","author":"T Bililign","year":"2004","unstructured":"Bililign, T., Hyun, C. G., Williams, J. S., Czisny, A. M. & Thorson, J. S. The hedamycin locus implicates a novel aromatic PKS priming mechanism. Chem. Biol. 11, 959\u2013969 (2004).","journal-title":"Chem. Biol."},{"key":"BFja201388_CR23","doi-asserted-by":"publisher","first-page":"2731","DOI":"10.1093\/molbev\/msr121","volume":"28","author":"K Tamura","year":"2011","unstructured":"Tamura, K. et al. MEGA5: molecular evolutionary genetics analysis using maximum likelihood, evolutionary distance, and maximum parsimony methods. Mol. Biol. Evol. 28, 2731\u20132739 (2011).","journal-title":"Mol. Biol. Evol."},{"key":"BFja201388_CR24","doi-asserted-by":"publisher","first-page":"742","DOI":"10.1039\/b407364a","volume":"22","author":"T Bililign","year":"2005","unstructured":"Bililign, T., Griffith, B. R. & Thorson, J. S. Structure, activity, synthesis and biosynthesis of aryl-C-glycosides. Nat. Prod. Rep. 22, 742\u2013760 (2005).","journal-title":"Nat. Prod. Rep."},{"key":"BFja201388_CR25","doi-asserted-by":"publisher","first-page":"4678","DOI":"10.1021\/ja029645k","volume":"125","author":"D Hoffmeister","year":"2003","unstructured":"Hoffmeister, D., Dr\u00e4ger, G., Ichinose, K., Rohr, J. & Bechthold, A. The C-glycosyltransferase UrdGT2 is unselective toward D-and L-configured nucleotide-bound rhodinoses. J. Am. Chem. Soc. 125, 4678\u20134679 (2003).","journal-title":"J. Am. Chem. Soc."},{"key":"BFja201388_CR26","doi-asserted-by":"publisher","first-page":"6056","DOI":"10.1021\/ja017385l","volume":"124","author":"A Trefzer","year":"2002","unstructured":"Trefzer, A. et al. Rationally designed glycosylated premithramycins: hybrid aromatic polyketides using genes from three different biosynthetic pathways. J. Am. Chem. Soc. 124, 6056\u20136062 (2002).","journal-title":"J. Am. Chem. Soc."},{"key":"BFja201388_CR27","doi-asserted-by":"publisher","first-page":"2568","DOI":"10.1002\/cbic.201100540","volume":"12","author":"G Wang","year":"2011","unstructured":"Wang, G., Kharel, M. K., Pahari, P. & Rohr, J. Investigating Mithramycin deoxysugar biosynthesis: enzymatic total synthesis of TDP-D-olivose. Chembiochem. 12, 2568\u20132571 (2011).","journal-title":"Chembiochem."},{"key":"BFja201388_CR28","doi-asserted-by":"publisher","first-page":"6644","DOI":"10.1128\/AEM.01266-06","volume":"72","author":"M P\u00e9rez","year":"2006","unstructured":"P\u00e9rez, M. et al. Combinatorial biosynthesis of antitumor deoxysugar pathways in Streptomyces griseus: reconstitution of \u201cunnatural natural gene clusters\u201d for the biosynthesis of four 2, 6-d-dideoxyhexoses. Appl. Environ. Microbiol. 72, 6644\u20136652 (2006).","journal-title":"Appl. Environ. Microbiol."},{"key":"BFja201388_CR29","doi-asserted-by":"publisher","first-page":"1266","DOI":"10.1128\/AAC.44.5.1266-1275.2000","volume":"44","author":"I Aguirrezabalaga","year":"2000","unstructured":"Aguirrezabalaga, I. et al. Identification and expression of genes involved in biosynthesis of L-oleandrose and its intermediate L-olivose in the oleandomycin producer Streptomyces antibioticus. Antimicrob. Agents Chemother. 44, 1266\u20131275 (2000).","journal-title":"Antimicrob. Agents Chemother."},{"key":"BFja201388_CR30","doi-asserted-by":"publisher","first-page":"1453","DOI":"10.1016\/S0969-2126(98)00144-0","volume":"6","author":"M Rizzi","year":"1998","unstructured":"Rizzi, M. et al. GDP-4-keto-6-deoxy-D-mannose epimerase\/reductase from Escherichia coli, a key enzyme in the biosynthesis of GDP-L-fucose, displays the structural characteristics of the RED protein homology superfamily. Structure 6, 1453\u20131465 (1998).","journal-title":"Structure"},{"key":"BFja201388_CR31","doi-asserted-by":"publisher","first-page":"295","DOI":"10.1093\/glycob\/cwg035","volume":"13","author":"M M\u00e4ki","year":"2003","unstructured":"M\u00e4ki, M. et al. Cloning and functional expression of a novel GDP-6-deoxy-D-talose synthetase from Actinobacillus actinomycetemcomitans. Glycobiology 13, 295\u2013303 (2003).","journal-title":"Glycobiology"}],"container-title":["The Journal of Antibiotics"],"original-title":[],"language":"en","link":[{"URL":"http:\/\/www.nature.com\/articles\/ja201388.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"http:\/\/www.nature.com\/articles\/ja201388","content-type":"text\/html","content-version":"vor","intended-application":"text-mining"},{"URL":"http:\/\/www.nature.com\/articles\/ja201388.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,5,18]],"date-time":"2023-05-18T17:20:07Z","timestamp":1684430407000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.nature.com\/articles\/ja201388"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2013,9,11]]},"references-count":31,"journal-issue":{"issue":"1","published-print":{"date-parts":[[2014,1]]}},"alternative-id":["BFja201388"],"URL":"https:\/\/doi.org\/10.1038\/ja.2013.88","relation":{},"ISSN":["0021-8820","1881-1469"],"issn-type":[{"value":"0021-8820","type":"print"},{"value":"1881-1469","type":"electronic"}],"subject":[],"published":{"date-parts":[[2013,9,11]]}}}