Conversion of DNA methyltransferases into azidonucleosidyl transferases via synthetic cofactors

Nucleic Acids Research

Volumn 33, Issue 5, 2005, Pages 1644-1652

  Comstock, Lindsay R ^a   Rajski, Scott R ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AZIDONUCLEOSIDYL TRANSFERASE; DNA METHYLTRANSFERASE; DOUBLE STRANDED DNA; PHOSPHINE DERIVATIVE; TRANSFERASE; UNCLASSIFIED DRUG; AZIDE; AZIRIDINE DERIVATIVE; DNA; DNA MODIFICATION METHYLASE ECORI; DNA MODIFICATION METHYLASE TAQI; GLYCOSYLTRANSFERASE; NUCLEOSIDE; OLIGONUCLEOTIDE; SITE SPECIFIC DNA METHYLTRANSFERASE (ADENINE SPECIFIC);

ARTICLE; CONTROLLED STUDY; DNA ALKYLATION; DNA METHYLATION; DNA MODIFICATION; ENZYME ANALYSIS; ENZYME METABOLISM; ENZYME MODIFICATION; PRIORITY JOURNAL; STAUDINGER REACTION; ALKYLATION; BIOTINYLATION; CHEMISTRY; COENZYME; METABOLISM; MOLECULAR MIMICRY; SYNTHESIS;

ALKYLATION; AZIDES; AZIRIDINES; BIOTINYLATION; COENZYMES; DNA; MOLECULAR MIMICRY; NUCLEOSIDES; OLIGONUCLEOTIDES; PENTOSYLTRANSFERASES; SITE-SPECIFIC DNA-METHYLTRANSFERASE (ADENINE-SPECIFIC);

EID: 15044352655     PISSN: 03051048     EISSN: 13624962     Source Type: Journal    
DOI: 10.1093/nar/gki306     Document Type: Article

References (38)

1. Nakayama,J., Rice,J.C., Strahl,B.D., Allis,C.D. and Grewal,S.I. (2001) Role of histone H3 lysine 9 methylation in epigenetic control of heterochromatin assembly. [i#Science#1i], [b#292#1b], 110-113.
2. Cheung,P., Allis,C.D. and Sassone-Corsi,P. (2000) Signaling to chromatin through histone modifications. [i#Cell#1i], [b#103#1b], 263-271.
3. Jenuwein,T. and Allis,C.D. (2001) Translating the histone code. [i#Science#1i], [b#293#1b], 1074-1080.
4. Xu,W., Chen,H., Du,K., Asahara,H., Tini,M., Emerson,B.M., Montminy,M. and Evans,R.M. (2001) A transcriptional switch mediated by cofactor methylation. [i#Science#1i], [b#294#1b], 2507-2511.
5. Chen,D., Ma,H., Hong,H., Koh,S.S., Huang,S.M., Schurter,B.T., Aswad,D.W. and Stallcup,M.R. (1999) Regulation of transcription by a protein methyltransferase. [i#Science#1i], [b#284#1b], 2174-2177.
6. Turner,B.M. (2002) Cellular memory and the histone code. [i#Cell#1i], [b#111#1b], 285-291.
7. Robertson,K.D. (2001) DNA methylation, methyltransferases, and cancer. [i#Oncogene#1i], [b#20#1b], 3139-3155.
8. Patra,S.K., Patra,A. and Dahiya,R. (2001) Histone deacetylase and DNA methyltransferase in human prostate cancer. [i#Biochem. Biophs. Res. Comm.#1i], [b#287#1b], 705-713.
9. Szyf,M. (2001) Towards a pharmacology of DNA methylation. [i#Trends Pharmacol. Sci.#1i], [b#22#1b], 350-354.
10. Pignot,M., Siethoff,C., Linscheid,M. and Weinhold,E. (1998) Coupling of a nucleoside with DNA by a methyltransferase. [i#Angew. Chem. Int. Ed.#1i] [b#37#1b], 2888-2891.
11. Pignot,M., Siethoff,C., Linscheid,M. and Weinhold,E. (2000) European patent WO 00/06578.
12. Pljevaljcic,G., Pignot,M. and Weinhold,E. (2003) Design of a new fluorescent cofactor for DNA methyltransferases and sequence-specific labeling of DNA. [i#J. Am. Chem. Soc.#1i], [b#125#1b], 3486-3492.
13. Pljevaljcic,G., Schmidt,F. and Weinhold,E. (2004) Sequence-specific methyltransferase-induced labeling of DNA (SMILing DNA). [i#ChemBioChem#1i] [b#5#1b], 265-269.
14. Saxon,E. and Bertozzi,C.R. (2000) Cell surface engineering by a modified Staudinger reaction. [i#Science#1i], [b#287#1b], 2007-2010.
15. Saxon,E., Luchansky,S.J., Hang,H.C., Yu,C., Lee,S.C. and Bertozzi,C.R. (2002) Investigating cellular metabolism of synthetic azidosugars with the Staudinger ligation. [i#J. Am. Chem. Soc.#1i], [b#124#1b], 14893-14902.
16. Kiick,K.L, Saxon,E., Tirrell,D.A. and Bertozzi,C.R. (2002) Incorporation of azides into recombinant proteins for chemoselective modification by the Staudinger ligation. [i#Proc. Natl Acad. Sci. USA#1i], [b#99#1b], 19-24.
17. Kho,Y., Kim,S.C., Jiang,C., Barma,D., Kwon,S.W., Cheng,J., Jaunbergs,J., Weinbaum,C., Tamanoi,F., Falck,J. [i#et al.#1i] (2004) A tagging-via-substrate technology for detection and proteomics of farnesylated proteins. [i#Proc. Natl Acad. Sci. USA#1i], [b#101#1b], 12479-12484.
18. Link,A.J. and Tirrell,D.A. (2003) Cell surface labeling of [i#Escherichia coli#1i] via copper(I)-catalyzed [3+2] cycloaddition. [i#J. Am. Chem. Soc.#1i], [b#125#1b], 11164-11165.
19. Speers,A.E., Adam,G.C. and Cravatt,B.F. (2003) Activity-based protein profiling in vivo using a copper(I)-catalyzed azide-alkyne [3+2] cycloaddition. [i#J. Am. Chem. Soc.#1i], [b#125#1b], 4686-4687.
20. Kolb,H.C., Finn,M.G. and Sharpless,K.B. (2001) Click chemistry: Diverse chemical function from a few good reactions. [i#Angew. Chem. Int. Ed.#1i] [b#40#1b], 2004-2021.
21. Restituyo,J.A., Comstock,L.R., Petersen,S.G., Stringfellow,T. and Rajski,S.R. (2003) Conversion of aryl azides to O-alkyl imidates via modified Staudinger ligation. [i#Org. Lett.#1i], [b#5#1b], 4357-4360.
22. Reich,N.O. and Everett,E.A. (1990) Identification of peptides involved in S-adenosylmethionine binding in the EcoRI DNA methylase. [i#J. Biol. Chem.#1i], [b#265#1b], 8929-8934.
23. Kaiser,I.I., Kladianos,D.M., Van Kirk,E.A. and Haley,B.E. (1983) Photoaffinity labeling of catechol O-methyltransferase with 8-azido-S-adenosylmethionine. [i#J. Biol. Chem.#1i], [b#258#1b], 1747-1751.
24. Syvanen,A.C., Laaksonen,M. and Soderlund,H. (1986) Fast quantification of nucleic acid hybrids by affinity-based hybrid collection. [i#Nucleic Acids Res.#1i], [b#14#1b], 5037-5048.
25. Comstock,L.R. and Rajski,S.R. (2004) Efficient synthesis of azide-bearing cofactor mimics. [i#J. Org. Chem.#1i], [b#69#1b], 1425-1428.
26. Sambrook,J. and Russell,D. (2001) [i#Molecular Cloning: A Laboratory Manual#1i]. Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY, pp. 9.68-9.69, 10.20-10.21.
27. Comstock,L.R. and Rajski,S.R. (2002) Expeditious synthesis of aziridine based cofactor mimics. [i#Tetrahedron#1i], [b#58#1b], 6019-6026.
28. Kolb,M. and Barth,J. (1985) Synthesis of 5′-[(3-aminooxypropyl)-amino]-5′-deoxyadenosine. [i#Liebigs Ann. Chem.#1i], 1036-1040.
29. Urata,H., Miyagoshi,H., Yumoto,T. and Akagi,M. (1999) Racemic synthesis of carbocyclic purine nucleoside analogues with restricted glycosyl conformation. [i#J. Chem. Soc. Perkin Trans.#1i], [b#1#1b], 1833-1838.
30. Gano,K.W., Monbouquette,H.G. and Myles,D.C. (2001) An efficient synthesis of a class of heterobifunctional photo-reactive crosslinkers, labels, and probes. [i#Tetrahedron Lett.#1i], [b#42#1b], 2249-2251.
31. Lee,J.W., Jun,S.I. and Kom,K. (2001) An efficient and practical method for the synthesis of mono-N-protected α,ω-diaminoalknaes. [i#Tetrahedron Lett.#1i], [b#42#1b], 2709-2711.
32. 8-Disubstituted adenosine derivatives as partial agonists for adenosine A1 receptors. [i#J. Med. Chem.#1i], [b#39#1b], 1463-1471.
33. Sakaitani,M. and Ohfune,Y. (1990) Syntheses and reactions of silyl carbamates. 1. Chemoselective transformation of amino protecting groups via tert-butyldimethylsilyl carbamates. [i#J. Org. Chem.#1i], [b#55#1b], 870-876.
34. Lindstrom,U.M. and Somfai,P. (1998) Aminolysis of vinyl epoxides as an efficient entry to N-H vinylaziridines. [i#Synthesis#1i], 109-117.
35. Van der Wende,E.M., Carnielli,M., Roelen,H.C.P.F., Lorenzen,A., von Frijtag Drabe Kunzel,J.K. and IJzerman,A.P. (1998) 5′-Substituted adenosine analogs as new high-affinity partial agonists for the adenosine A1 receptor. [i#J. Med. Chem.#1i], [b#41#1b], 102-108.
36. Kanan,M.W., Rozenman,M.M., Sakurai,K., Snyder,T.M. and Liu,D.R. (2004) Reaction discovery enabled by DNA-templated synthesis and in vitro selection. [i#Nature#1i], [b#431#1b], 545-549.
37. Erdem,G., Oner,C., Onal,A.M., Kisakurek,D. and Oaus,A. (1994) Free radical mediated interaction of ascorbic acid and ascorbate/Cu(II) with viral and plasmid DNAs. [i#J. Biosci.#1i], [b#19#1b], 9-17.
38. Wilchek,M. and Bayer,E.A. (1988) The avidin-biotin complex in bioanalytical applications. [i#Anal. Biochem.#1i], [b#171#1b], 1-32.