English
 
User Manual Privacy Policy Disclaimer Contact us
  Advanced SearchBrowse

Item

ITEM ACTIONSEXPORT
  Synthesis of S-adenosyl-L-methionine analogs and their use for sequence-specific transalkylation of DNA by methyltransferases.

Dalhoff, C., Lukinavicius, G., Klimašauskas, S., & Weinhold, E. (2006). Synthesis of S-adenosyl-L-methionine analogs and their use for sequence-specific transalkylation of DNA by methyltransferases. Nature Protocols, 1, 1879-1886. doi:10.1038/nprot.2006.253.

Item is

Basic

show hide
Item Permalink: http://hdl.handle.net/21.11116/0000-0001-E21A-3 Version Permalink: http://hdl.handle.net/21.11116/0000-0001-E21D-0
Genre: Journal Article

Files

show Files
hide Files
:
2630067.pdf (Publisher version), 291KB
 
File Permalink:
-
Name:
2630067.pdf
Description:
-
Visibility:
Restricted (Max Planck Institute for Biophysical Chemistry (Karl Friedrich Bonhoeffer Institute), Göttingen; )
MIME-Type / Checksum:
application/pdf
Technical Metadata:
Copyright Date:
-
Copyright Info:
-
License:
-

Locators

show

Creators

show
hide
 Creators:
Dalhoff, C., Author
Lukinavicius, G.1, Author              
Klimašauskas, S., Author
Weinhold, E., Author
Affiliations:
1Laboratory of Chromatin Labeling and Imaging, Max Planck Institute for Biophysical Chemistry, Max Planck Society, ou_2616691              

Content

show
hide
Free keywords: -
 Abstract: Here we describe a one-step synthetic procedure for the preparation of S-adenosyl-L-methionine (AdoMet) analogs with extended carbon chains replacing the methyl group. These AdoMet analogs function as efficient cofactors for DNA methyltransferases (MTases), and we provide a protocol for sequence-specific transfer of extended side chains from these AdoMet analogs to DNA by DNA MTases. Direct chemoselective allylation or propargylation of S-adenosyl-L-homocysteine (AdoHcy) at sulfur is achieved under the acidic conditions needed to protect other nucleophilic positions in AdoHcy. The unsaturated bonds in beta position to the sulfonium center of the resulting AdoMet analogs are designed to stabilize the transition state formed upon DNA MTase-catalyzed nucleophilic attack at the carbon next to the sulfonium center and lead to efficient transfer of the extended side chains to DNA. Using these protocols, sequence-specific functionalized DNA can be obtained within one to two weeks.

Details

show
hide
Language(s): eng - English
 Dates: 2006-11-222006
 Publication Status: Published in print
 Pages: -
 Publishing info: -
 Table of Contents: -
 Rev. Method: Peer
 Identifiers: DOI: 10.1038/nprot.2006.253
 Degree: -

Event

show

Legal Case

show

Project information

show

Source 1

show
hide
Title: Nature Protocols
Source Genre: Journal
 Creator(s):
Affiliations:
Publ. Info: -
Pages: - Volume / Issue: 1 Sequence Number: - Start / End Page: 1879 - 1886 Identifier: -