Dual Role of S-Adenosylmethionine (SAM+) in the Methylation of sp2-Hybridized Electrophilic Carbons

被引：12

作者：

Buckel, Wolfgang ^{[1
]}

Thauer, Rudolf K. ^{[1
]}

机构：

[1] Max Planck Inst Terr Mikrobiol, D-35043 Marburg, Germany

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2011年 / 50卷 / 45期

关键词：

active sites; radicals; reaction mechanisms; transferases; BIOSYNTHESIS; METHYLTRANSFERASES; MECHANISM; ENZYMES; RNA; SYNTHASE; COMPLEX; GENE; CFR;

D O I：

10.1002/anie.201105076

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A surprising mechanism: The enzymatic methylation of adenosine at C-2 consumes two molecules of S-adenosylmethionine (SAM +), one in the S N2 transfer of its methyl group to an active-site cysteine of the methyltransferase, and a second in the formation of a 5′-deoxyadenosine radical (5′-A .) that abstracts a hydrogen atom from the protein-bound methyl group enabling it to attack at C-2 of the adenosine (see scheme). Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：10492 / 10494

页数：3

共 23 条

[1] Structural Basis for Methyl Transfer by a Radical SAM Enzyme
Boal, Amie K.
Grove, Tyler L.
McLaughlin, Monica I.
Yennawar, Neela H.
Booker, Squire J.
Rosenzweig, Amy C.
[J]. SCIENCE, 2011, 332 (6033) : 1089 - 1092
[2] Buckel W., 2011, HDB RADICALS CHEM BI, V3
[3] Buckel W., 2009, ANGEW CHEM, V121, P6911
[4] Radical and Electron Recycling in Catalysis
Buckel, Wolfgang
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (37) : 6779 - 6787
[5] Radical S-adenosylmethionine enzymes: Mechanism, control and function
Challand, Martin R.
Driesener, Rebecca C.
Roach, Peter L.
[J]. NATURAL PRODUCT REPORTS, 2011, 28 (10) : 1696 - 1721
[6] Bacteriochlorophyllide c C-82 and C-121 Methyltransferases are essential for adaptation to low light in Chlorobaculum tepidum
Chew, Aline Gomez Maqueo
Frigaard, Niels-Ulrik
Bryant, Donald A.
[J]. JOURNAL OF BACTERIOLOGY, 2007, 189 (17) : 6176 - 6184
[7] Insight into the reaction mechanism of the Escherichia coli cyclopropane fatty acid synthase: Isotope exchange and kinetic isotope effects
E, Guangqi
Lesage, Denis
Ploux, Olivier
[J]. BIOCHIMIE, 2010, 92 (10) : 1454 - 1457
[8] FORMATION OF 2-METHYLTRYPTOPHAN IN THE BIOSYNTHESIS OF THIOSTREPTON - ISOLATION OF S-ADENOSYLMETHIONINE - TRYPTOPHAN 2-METHYLTRANSFERASE
FRENZEL, T
ZHOU, P
FLOSS, HG
[J]. ARCHIVES OF BIOCHEMISTRY AND BIOPHYSICS, 1990, 278 (01) : 35 - 40
[9] A Radically Different Mechanism for S-Adenosylmethionine-Dependent Methyltransferases
Grove, Tyler L.
Benner, Jack S.
Radle, Matthew I.
Ahlum, Jessica H.
Landgraf, Bradley J.
Krebs, Carsten
Booker, Squire J.
[J]. SCIENCE, 2011, 332 (6029) : 604 - 607
[10] The activity of Escherichia coli cyclopropane fatty acid synthase depends on the presence of bicarbonate
Iwig, DF
Uchida, A
Stromberg, JA
Booker, SJ
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (33) : 11612 - 11613

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