Brasilinolide Synthesis Essay

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  • 1. Wilson JW. 2012. Nocardiosis: updates and clinical overview. Mayo Clin Proc87:403–407. doi:10.1016/j.mayocp.2011.11.016. [PMC free article][PubMed][Cross Ref]

    2. Xia L, Cai J, Wang B, Huang Y, Jian J, Lu Y. 2015. Draft genome sequence of Nocardia seriolae ZJ0503, a fish pathogen isolated from Trachinotus ovatus in China. Genome Announc3(1):e01223-14. doi:10.1128/genomeA.01223-14. [PMC free article][PubMed][Cross Ref]

    3. Tan CK, Lai CC, Lin SH, Liao CH, Chou CH, Hsu HL, Huang YT, Hsueh PR. 2010. Clinical and microbiological characteristics of nocardiosis including those caused by emerging Nocardia species in Taiwan, 1998–2008. Clin Microbiol Infect16:966–972. doi:10.1111/j.1469-0691.2009.02950.x. [PubMed][Cross Ref]

    4. Tanaka Y, Komaki H, Yazawa K, Mikami Y, Nemoto A, Tojyo T, Kadowaki K, Shigemori H, Kobayashi J. 1997. Brasilinolide A, a new macrolide antibiotic produced by Nocardia brasiliensis: producing strain, isolation and biological activity. J Antibiot50:1036–1041. doi:10.7164/antibiotics.50.1036. [PubMed][Cross Ref]

    5. Komatsu K, Tsuda M, Tanaka Y, Mikami Y, Kobayashi J. 2004. Absolute stereochemistry of immunosuppressive macrolide brasilinolide A and its new congener brasilinolide C. J Org Chem69:1535–1541. doi:10.1021/jo035773v. [PubMed][Cross Ref]

    6. Shigemori H, Komaki H, Yazawa K, Mikami Y, Nemoto A, Tanaka Y, Sasaki T, In Y, Ishida T, Kobayashi J. 1998. Brasilicardin A. A novel tricyclic metabolite with potent immunosuppressive activity from actinomycete Nocardia brasiliensis. J Org Chem63:6900–6904. doi:10.1021/jo9807114. [PubMed][Cross Ref]

    7. Komaki H, Nemoto A, Tanaka Y, Takagi H, Yazawa K, Mikami Y, Shigemori H, Kobayashi J, Ando A, Nagata Y. 1999. Brasilicardin A, a new terpenoid antibiotic from the pathogenic Nocardia brasiliensis: fermentation, isolation and biological activity. J Antibiot52:13–19. doi:10.7164/antibiotics.52.13. [PubMed][Cross Ref]

    8. Komatsu K, Tsuda M, Shiro M, Tanaka Y, Mikami Y, Kobayashi J. 2004. Brasilicardins B–D, new tricyclic terpenoids from actinomycete Nocardia brasiliensis. Bioorg Med Chem12:5545–5551. doi:10.1016/j.bmc.2004.08.007. [PubMed][Cross Ref]

    9. Komatsu K, Tsuda M, Tanaka Y, Mikami Y, Kobayashi J. 2005. SAR studies of brasilicardin A for immunosuppressive and cytotoxic activities. Bioorg Med Chem13:1507–1513. doi:10.1016/j.bmc.2004.12.029. [PubMed][Cross Ref]

    10. Usui T, Nagumo Y, Watanabe A, Kubota T, Komatsu K, Kobayashi J, Osada H. 2006. Brasilicardin A, a natural immunosuppressant, targets amino acid transport system L. Chem Biol13:1153–1160. doi:10.1016/j.chembiol.2006.09.006. [PubMed][Cross Ref]

    11. Coltart DM, Danishefsky SJ. 2003. Novel synthetic approach to the 8,10-dimethyl-anti-syn.-anti-perhydrophenanthrene skeleton. Org Lett5:1289–1292. doi:10.1021/ol034213f. [PubMed][Cross Ref]

    12. Jung ME, Perez F, Regan CF, Yi SW, Perron Q. 2013. Se-phenyl prop-2-eneselenoate: an ethylene equivalent for Diels-Alder reactions. Angew Chem Int Ed52:2060–2062. doi:10.1002/anie.201208294. [PubMed][Cross Ref]

    13. Jung ME, Chamberlain BT, Koch P, Niazi KR. 2015. Synthesis and bioactivity of a brasilicardin A analogue featuring a simplified core. Org Lett17:3608–3611. doi:10.1021/acs.orglett.5b01712. [PubMed][Cross Ref]

    14. Hayashi Y, Matsuura N, Toshima H, Itoh N, Ishikawa J, Mikami Y, Dairi T. 2008. Cloning of the gene cluster responsible for the biosynthesis of brasilicardin A, a unique diterpenoid. J Antibiot61:164–174. doi:10.1038/ja.2008.126. [PubMed][Cross Ref]

    15. Chikhi R, Medvedev P. 2014. Informed and automated k-mer size selection for genome assembly. Bioinformatics30:31–37. doi:10.1093/bioinformatics/btt310. [PubMed][Cross Ref]

    16. Chaisson MJ, Tesler G. 2012. Mapping single molecule sequencing reads using basic local alignment with successive refinement (BLASR): application and theory. BMC Bioinformatics13:238. doi:10.1186/1471-2105-13-238. [PMC free article][PubMed][Cross Ref]

    17. Boetzer M, Pirovano W. 2014. SSPACE-LongRead: scaffolding bacterial draft genomes using long read sequence information. BMC Bioinformatics15:211. doi:10.1186/1471-2105-15-211. [PMC free article][PubMed][Cross Ref]

    18. Boetzer M, Pirovano W. 2012. Toward almost closed genomes with GapFiller. Genome Biol13:R56. doi:10.1186/gb-2012-13-6-r56. [PMC free article][PubMed][Cross Ref]

    19. Weber T, Blin K, Duddela S, Krug D, Kim HU, Bruccoleri R, Lee SY, Fischbach MA, Müller R, Wohlleben W, Breitling R, Takano E, Medema MH. 2015. antiSMASH 3.0—a comprehensive resource for the genome mining of biosynthetic gene clusters. Nucleic Acids Res43:W237–W243. doi:10.1093/nar/gkv437. [PMC free article][PubMed][Cross Ref]

    20. Chiu HT, Weng CP, Lin YC, Chen KH. 2016. Target-specific identification and characterization of the putative gene cluster for brasilinolide biosynthesis revealing the mechanistic insights and combinatorial synthetic utility of 2-deoxy-l-fucose biosynthetic enzymes. Org Biomol Chem14:1988–2006. doi:10.1039/c5ob02292d. [PubMed][Cross Ref]

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