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Scaglione, Jamie B.,Akey, David L.,Sullivan, Rachel,Kittendorf, Jeffrey D.,Rath, Christopher M.,Kim, Eung-Soo,Smith, Janet L.,Sherman, David H. WILEY-VCH Verlag 2010 Angewandte Chemie Vol.49 No.33
<B>Graphic Abstract</B> <P>A narrow tunnel: Biochemical and structural analysis of the tautomycetin thioesterase (TE) has provided the first high-resolution structure of a linear-chain-terminating TE in polyketide biosynthesis, showing the enzyme to be stereoselective with a constrained substrate chamber relative to macrolactone-forming thioesterases. <img src='wiley_img_2010/14337851-2010-49-33-ANIE201000032-content.gif' alt='wiley_img_2010/14337851-2010-49-33-ANIE201000032-content'> </P>
Biocatalytic Synthesis of Pikromycin, Methymycin, Neomethymycin, Novamethymycin, and Ketomethymycin
Hansen, Douglas A.,Rath, Christopher M.,Eisman, Eli B.,Narayan, Alison R. H.,Kittendorf, Jeffrey D.,Mortison, Jonathan D.,Yoon, Yeo Joon,Sherman, David H. American Chemical Society 2013 JOURNAL OF THE AMERICAN CHEMICAL SOCIETY - Vol.135 No.30
<P>A biocatalytic platform that employs the final two monomodular type I polyketide synthases of the pikromycin pathway in vitro followed by direct appendage of <SMALL>d</SMALL>-desosamine and final C–H oxidation(s) in vivo was developed and applied toward the synthesis of a suite of 12- and 14-membered ring macrolide natural products. This methodology delivered both compound classes in 13 steps (longest linear sequence) from commercially available (<I>R</I>)-Roche ester in >10% overall yields.</P><P><B>Graphic Abstract</B> <IMG SRC='http://pubs.acs.org/appl/literatum/publisher/achs/journals/content/jacsat/2013/jacsat.2013.135.issue-30/ja404134f/production/images/medium/ja-2013-04134f_0008.gif'></P><P><A href='http://pubs.acs.org/doi/suppl/10.1021/ja404134f'>ACS Electronic Supporting Info</A></P>