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. 2012 Jan 27;51(5):1216-20.
doi: 10.1002/anie.201105882. Epub 2011 Dec 23.

Enzymatic total synthesis of defucogilvocarcin M and its implications for gilvocarcin biosynthesis

Affiliations

Enzymatic total synthesis of defucogilvocarcin M and its implications for gilvocarcin biosynthesis

Pallab Pahari et al. Angew Chem Int Ed Engl. .
No abstract available

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Figures

Figure 1
Figure 1
HPLC traces of the enzymatic reactions for the synthesis of defucogilvocarcin M (1): A) Control reaction without acetyl-CoA and malonyl-CoA. B) Acetyl-CoA+malonyl-CoA+PKS enzymes. C) Acetyl-CoA + malonyl-CoA + PKS enzymes + post-PKS enzymes. D) Rabelomycin (12) standard. E) Defucogilvocarcin M (1) standard.
Figure 2
Figure 2
HPLC traces of the enzymatic reactions with prejadomycin (14) and UWM6 (10): A) Prejadomycin (14) + PKS-enzymes + post-PKS enzymes. B) Prejadomycin (14) standard. C) UWM6 (10) + PKS-enzymes + post-PKS enzymes. D) UWM6 (10) standard. E) Defucogilvocarcin M (1) standard.
Figure 3
Figure 3
HPLC traces of the enzymatic reactions: A) Acetyl CoA + malonyl-CoA + PKS enzymes + JadF produce prejadomycin (14). B) Prejadomycin (14) + GilOI. C) Dehydrorabelomycin (16) standard. D) Dehydrorabelomycin (16) + GilOII + GilM + GilMT + GilR produce defucogilvocarcin M 1.
Scheme 1
Scheme 1
Representative members of the gilvocarcin group of natural products.
Scheme 2
Scheme 2
Proposed gilvocarcin biosynthetic pathway.

References

    1. Fischer C, Lipata F, Rohr J. J. Am. Chem. Soc. 2003;125:7818–7819. - PMC - PubMed
    2. Takahashi K, Yoshida M, Tomita F, Shirahata K. J. Antibiot. 1981;34:271–275. - PubMed
    3. Hatano K, Hagashide E, Shibata M, Kameda Y, Horii S. Agric. Biol. Chem. 1980;44:1157–1163.
    4. Balitz DM, O’Herron FA, Bush J, Vyas DM, Nettleton DE, Grulich RE, Bradner WT, Doyle TW, Arnold E, Clardy J. J. Antibiot. 1981;34:1544–1555. - PubMed
    1. Sehgal SN, Czerkawski H, Kudelski A, Pandev K, Saucier R, Vezina C. J. Antibiot. 1983;36:355–361. - PubMed
    2. Weiss U, Yoshihira K, Highet RJ, White RJ, Wei TT. J. Antibiot. 1982;35:1194–1201. - PubMed
    3. Li YQ, Huang XS, Ishida K, Maier A, Kelter G, Jiang Y, Peschel G, Menzel KD, Li MG, Wen ML, Xu LH, Grabley S, Fiebig HH, Jiang CL, Hertweck C, Sattler I. Org. Biomol. Chem. 2008;6:3601–3605. - PubMed
    4. Nakajima S, Kojiri K, Suda H, Okanishi M. J. Antibiot. 1991;44:1061–1064. - PubMed
    5. Yamashita N, Shin-ya K, Furihata K, Hayakawa Y, Seto H. J. Antibiot. 1998;51:1105–1108. - PubMed
    1. Matsumoto A, Hanawalt PC. Cancer Res. 2000;60:3921–3926. - PubMed
    1. Elespuru RK, Gonda SK. Science. 1984;223:69–71. - PubMed
    2. Tse-Dinh Y-C, McGee LR. Biochem. Biophys. Res. Commun. 1987;143:808–812. - PubMed
    3. McGee LR, Misra R. J. Am. Chem. Soc. 1990;112:2386–2389.
    1. Morimoto M, Okubo S, Tomita F, Marumo H. J. Antibiot. 1981;34:701–707. - PubMed
    2. Matsumoto A, Fujiwara Y, Elespuru RK, Hanawalt PC. Photochem. Photobiol. 1994;60:225–230. - PubMed

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