A new strategy for aromatic ring alkylation in cylindrocyclophane biosynthesis.
作者： Hitomi Nakamura , Erica E Schultz , Emily P Balskus
关键词: Ring (chemistry) 、 Alkylation 、 Metabolic engineering 、 Stereochemistry 、 Biocatalysis 、 Organic synthesis 、 Chemistry 、 Aromaticity 、 Alkyl 、 Organic chemistry 、 Stereospecificity
摘要: Alkylation of aromatic rings with alkyl halides is an important transformation in organic synthesis, yet enzymatic equivalent unknown. Here, we report that cylindrocyclophane biosynthesis Cylindrospermum licheniforme ATCC 29412 involves chlorination unactivated carbon center by a novel halogenase, followed previously uncharacterized dimerization reaction featuring sequential, stereospecific alkylations resorcinol rings. Discovery the machinery underlying this unique biosynthetic carbon-carbon bond formation has implications for biocatalysis and metabolic engineering.
nature.com
core.ac.uk
sci-hub.se 参考文章(56)
M C Kennedy, T A Kent, M Emptage, H Merkle, H Beinert, E Münck, Evidence for the formation of a linear [3Fe-4S] cluster in partially unfolded aconitase. Journal of Biological Chemistry. ,vol. 259, pp. 14463- 14471 ,(1984) , 10.1016/S0021-9258(17)42622-6
Narayanan Eswar, Ben Webb, Marc A. Marti‐Renom, M.S. Madhusudhan, David Eramian, Min‐yi Shen, Ursula Pieper, Andrej Sali, Comparative protein structure modeling using Modeller. Current protocols in human genetics. ,vol. 47, ,(2006) , 10.1002/0471250953.BI0506S15
George A. Olah, V. Prakash Reddy, G. K. Surya Prakash, Friedel‐Crafts Reactions Kirk-Othmer Encyclopedia of Chemical Technology. pp. 1- 49 ,(2000) , 10.1002/0471238961.0618090515120108.A01
Liangcai Gu, Bo Wang, Amol Kulkarni, Todd W. Geders, Rashel V. Grindberg, Lena Gerwick, Kristina Håkansson, Peter Wipf, Janet L. Smith, William H. Gerwick, David H. Sherman, Metamorphic enzyme assembly in polyketide diversification Nature. ,vol. 459, pp. 731- 735 ,(2009) , 10.1038/NATURE07870
Bradley S. Moore, Jian Lu Chen, Gregory M. L. Patterson, Richard E. Moore, Linda S. Brinen, Yoko Kato, Jon Clardy, [7.7]Paracyclophanes from blue-green algae Journal of the American Chemical Society. ,vol. 112, pp. 4061- 4063 ,(1990) , 10.1021/JA00166A066
Edith Buchinger, Daniel H. Knudsen, Manja A. Behrens, Jan Skov Pedersen, Olav A. Aarstad, Anne Tøndervik, Svein Valla, Gudmund Skjåk-Bræk, Reinhard Wimmer, Finn L. Aachmann, Structural and functional characterization of the R-modules in alginate C-5 epimerases AlgE4 and AlgE6 from Azotobacter vinelandii. Journal of Biological Chemistry. ,vol. 289, pp. 31382- 31396 ,(2014) , 10.1074/JBC.M114.567008
Frank J. Slack, Gary Ruvkun, A novel repeat domain that is often associated with RING finger and B-box motifs. Trends in Biochemical Sciences. ,vol. 23, pp. 474- 475 ,(1998) , 10.1016/S0968-0004(98)01299-7
Kateryna Fesko, Mandana Gruber-Khadjawi, Biocatalytic Methods for C ? C Bond Formation Chemcatchem. ,vol. 5, pp. 1248- 1272 ,(2013) , 10.1002/CCTC.201200709
Claudia Wagner, Mustafa El Omari, Gabriele M. König, Biohalogenation: Nature’s Way to Synthesize Halogenated Metabolites† Journal of Natural Products. ,vol. 72, pp. 540- 553 ,(2009) , 10.1021/NP800651M