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Taifo Mahmud Laboratory - Publications

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Ito, T.; Roongsawang, N.; Shirasaka, N.; Lu, W.; Flatt, P.M.; Kasanah, N.; Miranda, C.; Mahmud, T. Deciphering Pactamycin Biosynthesis and Engineered Production of Pactamycin Analogues. ChemBioChem 2009, 10, 2253-2265.

Xu, H.; Zhang, Y.; Yang, J.; Mahmud, T.; Bai, L.; Deng, Z. Alternative Epimerization in C7N-Aminocyclitol Biosynthesis Is Catalyzed by ValD, A Large Protein of the Vicinal Oxygen Chelate Superfamily. Chem. Biol. 2009, 16, 567-576.

Mahmud, T. Progress in Aminocyclitol Biosynthesis. Curr. Opin. Chem. Biol. 2009, 13, 161-170.

Fotso, S.; Zabriskie, T. M.;  Proteau, P.J.; Flatt, P.M.; Santosa, D.A.; Sulastri; Mahmud, T. Limazepines A-F, Pyrrolo[1,4]benzodiazepine Antibiotics from an Indonesian Micrococcus sp. J. Nat. Prod. 2009, 72, 690-695.

Wu, X.; Flatt, P. M.; Xu, H.; Mahmud, T. Biosynthetic gene cluster of cetoniacytone A, an unusual aminocyclitol from the endosymbiotic Bacterium Actinomyces sp. Lu 9419. Chembiochem 2009, 10, 304-314.         

Xu, H.; Yang, J.; Bai, L.; Deng, Z.; Mahmud, T. Genetically Engineered Production of 1,1´-bis-Valienamine and Validienamycin in Streptomyces hygroscopicus and Their Conversion to Valienamine. Appl. Microbiol. Biotechnol. 2009, 81, 895-902

Xu, H.; Minagawa, K.; Bai, L.; Deng, Z.; Mahmud, T. Catalytic Analysis of the Validamycin Glycosyltransferase (ValG) and Enzymatic Production of 4´´-epi-Validamycin A. J. Nat. Prod. 2008, 71, 1233-1236.

Choi, W.S.; Wu, X.; Choeng, Y.H.; Mahmud, T.; Jeong, B.C.; Lee, S.H.; Chang, Y.K.; Kim, C.J.; Hong, S.K.. Genetic organization of the putative salbostatin biosynthetic gene cluster including the 2-epi-5-epi-valiolone synthase gene in Streptomyces albus ATCC 21838. Appl. Microbiol. Biotechnol. 2008, 80, 637-645

Fotso, S.; Mahmud, T.; Zabriskie, T. M.; Santosa, D. A.; Sulastri; Proteau, P. J. Rearranged and Unrearranged Angucyclinones from an Indonesian Streptomyces spp. J. Antibiot. 2008, 61, 449-456.

Fotso, S.; Mahmud, T.; Zabriskie, T. M.; Santosa, D. A.; Sulastri; Proteau, P. J. Angucyclinones from an Indonesian Streptomyces sp. J. Nat. Prod. 2008, 71, 61-65.

Schneiker, S.; Perlova, O.; Kaiser, O.; Gerth, K.; Alici, A.; Altmeyer, MO.; Bartels, D.; Bekel, T.; Beyer, S.; Bode, E.; Bode, H. B.; Bolten, C. J.; Choudhuri, J. V.; Doss, S.; Elnakady, Y. A.; Frank, B.; Gaigalat, L.; Goesmann, A.; Groeger, C.; Gross, F.; Jelsbak, L.; Jelsbak, L.; Kalinowski, J.; Kegler, C.; Knauber, T.; Konietzny, S.; Kopp, M.; Krause, L.; Krug, D.; Linke, B.; Mahmud, T.; Martinez-Arias, R.; McHardy, A. C.; Merai, M.; Meyer, F.; Mormann, S.; Munoz-Dorado, J.; Perez, J.; Pradella, S.; Rachid, S.; Raddatz, G.; Rosenau, F.; Ruckert, C.; Sasse, F.; Scharfe, M.; Schuster, S. C.; Suen, G.; Treuner-Lange, A.; Velicer, G. J.; Vorholter, F. J.; Weissman, K. J.; Welch, R. D.; Wenzel, S. C.; Whitworth, D. E.; Wilhelm, S.; Wittmann, C.; Blocker, H.; Puhler, A.; Muller, R. Complete genome sequence of the myxobacterium Sorangium cellulosum. Nat. Biotechnol. 2007, 25, 1281-1289.

Mahmud, T. Isotope Tracer Investigations of Natural Products Biosynthesis: The Discovery of Novel Metabolic Pathways. J. Label. Comp. Radiopharm., 2007, 50, 1039-1051.

Bode, H. B.; Meiser, P.; Klefisch, T.; Cortina, N. S.; Krug, D.; Göhring, A.; Schwär, G.; Mahmud, T.; Müller, R. Mutasynthesis-derived myxalamids and origin of the isobutyryl-CoA starter unit of myxalamid B. ChemBioChem, 2007, 8, 2139-2144.

Mahmud, T.; Flatt, P. M.; Wu, X. Biosynthesis of Unusual Aminocyclitol-containing Natural Products. J. Nat. Prod. 2007, 70, 1384-1391.

Minagawa, K.; Zhang, Y.; Ito, T.; Bai, L.; Deng, Z.; Mahmud, T. ValC, a New Type of C7-Cyclitol Kinase Involved in the Biosynthesis of the Antifungal Agent Validamycin A, ChemBioChem, 2007, 8, 632-641.

Flatt, P.M.; Mahmud, T. Biosynthesis of Aminocyclitol-Aminoglycoside Antibiotics and Related Compounds. Nat. Prod. Rep., 2007, 24, 358-392.

Wu, X.; Flatt, P.M.; Schlörke, O.; Zeeck, A.; Dairi, T.; Mahmud, T. A Comparative Analysis of the Sugar Phosphate Cyclase Superfamily Involved in Primary and Secondary Metabolism. ChemBioChem, 2007, 8, 239-248.

Müller, I.; Weinig, S.; Steinmetz, H.; Kunze, B.; Veluthoor, S.; Mahmud, T.; Müller, R. A Unique Mechanism for Methyl Ester Formation via an Amide Intermediate Found in Myxobacteria, ChemBioChem, 2006, 7, 1197-1205.

Bai, L.; Li, L.; Xu, H.; Minagawa, K.; Yu, Y.; Zhang, Y.; Floss, H.G.; Zhou, X.; Mahmud, T.; Deng, Z. Functional Analysis of the Validamycin Biosynthetic Gene Cluster and Engineered Production of validoxylamine A, Chem. Biol., 2006, 13, 387-397.

Wenzel, S.C.; Meiser, P.; Binz, T.M.; Mahmud, T.; Müller, R. Nonribosomal Peptide Biosynthesis: Point Mutations and Module Skipping Lead to Chemical Diversity. Angew. Chem. Int. Ed., 2006, 45, 2296-2301.

Mahmud, T.; Wenzel, S.C.; Wan, E.; Wen, K.W.; Bode, H.B.; Gaitatzis, N.; Müller, R. A Novel Biosynthetic Pathway to Isovaleryl-CoA in Myxobacteria: The Involvement of the Mevalonate Pathway. ChemBioChem, 2005, 6, 322.

Yu, Y.; Bai, L.; Minagawa, K.; Jian, X.; Li, L.; Li, J.; Chen, S.; Cao, E.; Mahmud, T.; Floss, H.G.; Zhou, X.; Deng, Z. A gene cluster encoding validamycin biosynthesis in Streptomyces hygroscopicus var. jinggangensis 5008. Appl. Environ. Microbiol. 2005, 71, 5066.

Xiong, Y.; Wu, X.; Mahmud, T. A Homologue of the Mycobacterium tuberculosis PapA5 Protein, Rif-Orf20, Is an Acetyltransferase Involved in the Biosynthesis of Antitubercular Drug Rifamycin B by Amycolatopsis mediterranei S699. ChemBioChem, 2005, 6, 834.

Dickschat, J. S.; Bode, H. B.; Mahmud, T.; Müller, R.; Schulz, S. A Novel Type of Geosmin Biosynthesis in Myxobacteria, J. Org. Chem. 2005, 70, 5174.

Xu, J.; Wan, E.; Kim, C.J.; Floss, H.G.; Mahmud, T. Identification of Tailoring Genes Involved in the Formation of the Polyketide Backbone of Rifamycin B by Amycolatopsis mediterranei S699. Microbiology 2005, 151, 2515.

Weinig, S.; Hecht, H.-J.; Mahmud, T.; Müller, R. Melithiazol Biosynthesis: Further Insights into Myxobacterial PKS/NRPS Systems and Evidence for a New Subclass of Methyltransferases. Chem. Biol. 2003, 10, 939–952.

Weinig, S.; Mahmud, T.; Müller, R. Markerless Mutations in the Myxothiazol Biosynthetic Gene Cluster: A Delicate Megasynthetase with a Superfluous Nonribosomal Peptide Synthetase Domain. Chem. Biol. 2003, 10, 953–960.

Arakawa, K.; Bowers, S. G.; Michels, B.; Trin, V.; Mahmud, T. Biosynthetic studies on the alpha-glucosidase inhibitor acarbose: The chemical synthesis of isotopically labeled 2-epi-5-epi-valiolone analogs. Carbohydr. Res. 2003, 338, 2075–2082.

Mahmud T. The C7N Aminocyclitol Family of Natural Products, Nat. Prod. Rep. 2003, 20, 137-166.

Xu, J.; Mahmud, T.; Floss, H.G.: Isolation and Characterization of 27-O-Demethylrifamycin SV Methyltransferase Provides New Insights Into the Post-PKS Modification Steps During the Biosynthesis of the Antitubercular Drug, Rifamycin B, by Amycolatopsis mediterranei S699, Arch. Biochem. Biophys., 2003, 411, 277-288.

Pullen, C. B.; Schmitz, P.; Hoffmann, D.; Meurer, K.; Boettcher, T.; von Bamberg, D.; Pereira, A. M.; França, S. C.; Hauser, M.; Geertsema, H.; Van Wyk, A.; Mahmud, T.; Floss, H. G.; Leistner, E.: Occurrence and Non-detectability of Maytansinoids in Individual Plants of the Genera Maytenus and Putterlickia, Phytochemistry, 2003, 62, 377-387.

Mahmud, T.
; Bode, H. B.; Silakowski, B.; Kroppenstedt, K-H.; Xu, M.; Nordhoff, S.; Höfle, G.; Müller, R.: A Novel Biosynthetic Pathway Providing Precursors For Fatty Acid Biosynthesis and Secondary Metabolite Formation in Myxobacteria, J. Biol. Chem., 2002, 277, 32768-32774.

Arakawa, K.; Müller, R.; Mahmud, T.; Yu, T-W.; Floss, H.G.: Characterization of the Early Stage Aminoshikimate Pathway in the Formation of 3-Amino-5-hydroxybenzoic Acid (AHBA): The RifN Protein Specifically Converts Kanosamine into Kanosamine 6-Phosphate, J. Am. Chem. Soc., 2002, 124, 10644-10645.

Moss, S.J.; Bai, L-q.; Toelzer, S.; Carroll, B.J.; Mahmud, T.; Yu, T-W.; Floss, H.G.: Identification of Asm19 as an Acyltransferase Attaching the Biologically Essential Ester Side Chain of Ansamitocins Using N-Desmethyl-4,5-desepoxymaytansinol, not Maytansinol, as Its substrate, J. Am. Chem. Soc., 2002, 124, 6544-6545.

Naganawa, H.; Hashizume, H.; Kubota, Y.; Sawa, R.; Takahashi, Y.; Arakawa, K.; Bowers, S.G.; Mahmud, T.: Biosynthesis of the Aminocyclitol Moiety of Pyralomicin 1a in Nonomuraea spiralis MI178-34F18, J. Antibiot., 2002, 55, 578-584.

Bowers, S.G.; Mahmud, T.; Floss H.G.: Biosynthetic Studies on the -Glucosidase Inhibitor Acarbose: The Chemical Synthesis of dTDP-4-amino-4,6-dideoxyglucose, Carbohydr. Res., 2002, 337, 297-304.

Mahmud, T.; Xu, J.; Choi, Y-U.: Synthesis of 5-Epi-[6-2H2]valiolone and Stereospecifically Monodeuterated 5-Epi-valiolones : Exploring the Steric Course of 5-Epi-valiolone Dehydratase in Validamycin A Biosynthesis, J. Org. Chem., 2001, 66, 5066-5073.

Mahmud, T.; Lee, S.; Floss H.G.: The Biosynthesis of Acarbose and Validamycin, Chem. Rec., 2001, 1, 300-310.

Dong, H.; Mahmud, T.; Tornus, I.; Wolf, E.; Lee, S.; Floss H.G.: Biosynthetic Studies on Validamycins. The Assembly Mechanism of the Pseudodisaccharide, Validoxylamine A, of Validamycin A, from the Cyclitols, J. Am. Chem. Soc., 2001, 123, 2733-2742.

Mahmud, T.; Tornus, I.; Wolf, E.; Egelkrout, E.; Uy, Ch.; Floss, H.G.; Lee, S. Biosynthetic Studies on the alpha-Glucosidase Inhibitor Acarbose in Actinoplanes sp.: 2-Epi-5-epi-valiolone Is the Direct Precursor of the Valienamine Moiety, J. Am. Chem. Soc. 1999, 121, 6973-6983.

Stratmann, A.; Mahmud, T.; Lee, S.; Distler, J.; Floss, H.G.; Piepersberg, W. The AcbC Protein from Actinoplanes sp. Is a C7-cyclitol Synthase Related to 3-Dehydroquinate Synthases and Is Involved in the Biosynthesis of the alpha-Glucosidase Inhibitor Acarbose, J. Biol.Chem. 1999, 274, 10889-10896.

Murakami, N.; Umezome, T.; Mahmud, T.; Sugimoto, M.; Kobayashi, M.; Wataya, Y.; Kim, H-S. Anti-malarial Activities of Acetylated Bruceolide Derivatives, Bioorg. Med. Chem. Lett. 1998, 8, 459-462.

Kobayashi, M.; Mahmud, T.; Umezome, T.; Wang, W.; Murakami, N.; Kitagawa, I. The Absolute Stereostructures of the Polyacetylenic Constituents of Ginseng Radix Rubra, Tetrahedron 1997, 53, 15691-15700.

Kobayashi, M.; Mahmud, T.; Yoshioka, N.; Shibuya, H.; Kitagawa, I. Indonesian Medicinal Plants. XXI.   Inhibitors of Na+/H+ Exchanger from the bark of Erythrina variegata and the Roots of Maclura cochinchinensis, Chem. Pharm. Bull. 1997, 45, 1615-1619.

Kobayashi, M.; Mahmud, T.; Yoshioka, N.; Hori, K.; Shibuya, H.; Kitagawa, I. Indonesian Medicinal Plants. XVIII.   Kompasinol A, a New Stilbeno-Phenylpropanoid from the Bark of Koompassia malaccensis (Fabaceae), Chem. Pharm. Bull. 1996, 44, 2249-2253.

Hirata, K.; Nakagami, H.; Takashina, J.; Mahmud, T.; Kobayashi, M.; In, Y.; Ishida, T.; Miyamoto, K. Novel Violet Pigment, Nostocine A, An Extracellular Metabolite from Cyanobacterium Nostoc spongiaeforme TISTR8169, Heterocycles 1996, 43, 1513-1519.

Kitagawa, I.; Mahmud, T.; Yokota, K.; Nakagawa, S.; Mayumi, T.; Kobayashi, M.; Shibuya, H. Indonesian Medicinal Plants. XVII.  Characterization of Quassinoids from the Stems of Quassia indica, Chem. Pharm. Bull. 1996, 44, 2009-2014.

Kitagawa, I.; Wei, H.; Nagao, S.; Mahmud, T.; Hori, K.; Kobayashi, M.; Uji, T.; Shibuya, H. Indonesian Medicinal Plants. XIV.  Characterization of 3'-O-Caffeoylsweroside, a New Phenolic Apioglucosides, from the Bark of Anthocephalus chinensis (Rubiaceae), Chem. Pharm. Bull. 1996, 44, 1162-1167.

Kitagawa, I.; Simanjuntak, P.; Mahmud, T.; Kobayashi, M.; Fujii, S.; Uji, T.; Shibuya, H. Indonesian Medicinal Plants. XIII. Chemical Structures of Caesaldekarins c, d, and e. Three Additional Cassane-Type Furanoditerpenes from the Roots of Caesalpinia major (Fabaceae).   Several Interesting Reaction Products of Caesaldekarin a Provided by N-Bromosuccinimide Treatment, Chem. Pharm. Bull. 1996, 44, 1157-1161.

Kobayashi, M.; Mahmud, T.; Tajima, H.; Wang, W.; Aoki, S.; Nakagawa, S.; Mayumi, T.; Kitagawa, I. Marine Natural Products. XXXVI.  Biologically Active Polyacetylenes, Adociacetylenes A, B, C, and D, from an Okinawan Marine Sponge of Adocia sp., Chem. Pharm. Bull. 1996, 44, 720-724.

Kobayashi, M.; Mahmud, T.; Umezome, T.; Kitagawa, I. The Absolute Stereostructure of Panaxytriol, A Biologically Active Diacetylenic Acetogenin, from Ginseng Radix Rubra, Chem. Pharm. Bull. 1995, 43, 1595-1597.

Kitagawa, I.; Mahmud, T.; Kobayashi, M.; Roemantyo; Shibuya, H. Taxol and Its Related Taxoids from the Needles of Taxus sumatrana, Chem. Pharm. Bull. 1995, 43, 365-367.

Kitagawa, I.; Mahmud, T.; Simanjuntak, P.; Hori, K.; Uji, T.; Shibuya, H. Indonesian Medicinal Plants. VIII.  Chemical Structures of Three New Triterpenoids, Bruceajavanin A, Dihydrobruceajavanin A, and Bruceajavanin B, and a New Alkaloidal Glycoside, Bruceacanthinoside, from the Stems of Brucea javanica (Simaroubaceae), Chem. Pharm. Bull. 1994, 42, 1416-1421.

Kitagawa, I.; Simanjuntak, P.; Hori, K.; Nagami, N.; Mahmud, T.; Shibuya, H.; Kobayashi, M. Indonesian Medicinal Plants. VII.  Seven New Clerodane-Type Diterpenoids, Peronemins A2, A3, B1, B2, B3, C1, and D1, from the Leaves of Peronema canescens (Verbenaceae), Chem. Pharm. Bull. 1994, 42, 1050-1055.

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