Halogenation strategies in natural product biosynthesis

被引:275
作者
Neumann, Christopher S. [1 ]
Fujimori, Danica Galonic [1 ]
Walsh, Christopher T. [1 ]
机构
[1] Harvard Univ, Sch Med, Dept Biol Chem & Mol Pharmacol, Boston, MA 02115 USA
来源
CHEMISTRY & BIOLOGY | 2008年 / 15卷 / 02期
关键词
D O I
10.1016/j.chembiol.2008.01.006
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Halogenation is a frequent modification of secondary metabolites and can play a significant role in establishing the bioactivity of a compound. Enzymatic halogenation through oxidative mechanisms is the most common route to these metabolites, though direct halogenation via halide anion incorporation is also known to proceed through both enzymatic and nonenzymatic pathways. In this article, we review the current state of knowledge regarding the mechanisms of these transformations, highlight applications of this knowledge, and propose future opportunities and challenges for the field.
引用
收藏
页码:99 / 109
页数:11
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共 70 条
[1]   NEW AMINO ACIDS FROM STREPTOMYCES [J].
ARGOUDELIS, AD ;
HERR, RR ;
MASON, DJ ;
PYKE, TR ;
ZIESER, JF .
BIOCHEMISTRY, 1967, 6 (01) :165-+
[2]   Biosynthetic convergence of salinosporamides A and B in the marine actinomycete Salinispora tropica [J].
Beer, Laura L. ;
Moore, Bradley S. .
ORGANIC LETTERS, 2007, 9 (05) :845-848
[3]   Crystal structure of the non-haem iron halogenase SyrB2 in syringomycin biosynthesis [J].
Blasiak, LC ;
Vaillancourt, FH ;
Walsh, CT ;
Drennan, CL .
NATURE, 2006, 440 (7082) :368-371
[4]   Mechanism of taurine:: α-ketoglutarate dioxygenase (TauD) from Escherichia coli [J].
Bollinger, JM ;
Price, JC ;
Hoffart, LM ;
Barr, EW ;
Krebs, C .
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2005, (21) :4245-4254
[5]   Kutznerides 1-4, depsipeptides from the actinomycete Kutzneria sp 744 inhabiting mycorrhizal roots of Picea abies seedlings [J].
Broberg, A ;
Menkis, A ;
Vasiliauskas, R .
JOURNAL OF NATURAL PRODUCTS, 2006, 69 (01) :97-102
[6]   Sporolides A and B:: Structurally unprecedented halogenated macrolides from the marine actinomycete Salinispora tropica [J].
Buchanan, GO ;
Williams, PG ;
Feling, RH ;
Kauffman, CA ;
Jensen, PR ;
Fenical, W .
ORGANIC LETTERS, 2005, 7 (13) :2731-2734
[7]   The complete genome sequence of the Arabidopsis and tomato pathogen Pseudomonas syringae pv. tomato DC3000 [J].
Buell, CR ;
Joardar, V ;
Lindeberg, M ;
Selengut, J ;
Paulsen, IT ;
Gwinn, ML ;
Dodson, RJ ;
Deboy, RT ;
Durkin, AS ;
Kolonay, JF ;
Madupu, R ;
Daugherty, S ;
Brinkac, L ;
Beanan, MJ ;
Haft, DH ;
Nelson, WC ;
Davidsen, T ;
Zafar, N ;
Zhou, LW ;
Liu, J ;
Yuan, QP ;
Khouri, H ;
Fedorova, N ;
Tran, B ;
Russell, D ;
Berry, K ;
Utterback, T ;
Van Aken, SE ;
Feldblyum, TV ;
D'Ascenzo, M ;
Deng, WL ;
Ramos, AR ;
Alfano, JR ;
Cartinhour, S ;
Chatterjee, AK ;
Delaney, TP ;
Lazarowitz, SG ;
Martin, GB ;
Schneider, DJ ;
Tang, XY ;
Bender, CL ;
White, O ;
Fraser, CM ;
Collmer, A .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2003, 100 (18) :10181-10186
[8]   The role of vanadium bromoperoxidase in the biosynthesis of halogenated marine natural products [J].
Butler, A ;
Carter-Franklin, JN .
NATURAL PRODUCT REPORTS, 2004, 21 (01) :180-188
[9]   Incorporation of nonmethyl branches by lsoprenoid-like logic:: Multiple β-alkylation events in the biosynthesis of myxovirescin A1 [J].
Calderone, Christopher T. ;
Iwig, David F. ;
Dorrestein, Pieter C. ;
Kelleher, Neil L. ;
Walsh, Christopher T. .
CHEMISTRY & BIOLOGY, 2007, 14 (07) :835-846
[10]   Dioxygen activation at mononuclear nonheme iron active sites: Enzymes, models, and intermediates [J].
Costas, M ;
Mehn, MP ;
Jensen, MP ;
Que, L .
CHEMICAL REVIEWS, 2004, 104 (02) :939-986