Fluorescent DNA: the development of 7-deazapurine nucleoside triphosphates applicable for sequencing at the single molecule level.
7-Deaza-2'-deoxyadenosine and -guanosine phosphoramidite building blocks as well as corresponding 5'-triphosphate derivatives are described carrying in position 7 substituents such as iodo, hexyn-1-yl or 5-aminopentyn-1-yl residues. The phosphoramidites were used to synthesize a series of modified oligodeoxynucleotides. A systematic study of the thermal stabilities of these oligonucleotide duplexes demonstrated that the 7-substituents are well accommodated in the major groove of B-DNA. The 7-(aminoalkyn-1-yl)-7-deazapurine 2'-deoxynucleoside triphosphates were labeled with bulky fluorophores such as Rhodamine Green(R) or tetramethylrhodamine.
Laboratorium für Organische und Bioorganische Chemie, Institut für Chemie, Universität Osnabrück, Barbarastr. 7, D-49069 Osnabrück, Germany. fraseela@rz.uni-osnabrueck.de
F
F
Seela
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E
Feiling
J
J
Gross
F
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Hillenkamp
N
N
Ramzaeva
H
H
Rosemeyer
M
M
Zulauf
D001671:Biochemistry / Q000379:methods*; D004247:DNA / Q000737:chemistry*; D003849:Deoxyguanosine / Q000031:analogs & derivatives / Q000737:chemistry; D004076:Digoxigenin / Q000737:chemistry; D005453:Fluorescence; D005456:Fluorescent Dyes / Q000737:chemistry*; D009692:Nucleic Acid Heteroduplexes; D011687:Purines / Q000737:chemistry*; D014372:Tubercidin / Q000031:analogs & derivatives / Q000737:chemistry
D005456:Fluorescent Dyes; D009692:Nucleic Acid Heteroduplexes; D011687:Purines; C053222:2'-deoxytubercidin; C045550:7-deaza-2'-deoxyguanosine; D004247:DNA; D003849:Deoxyguanosine; D014372:Tubercidin; D004076:Digoxigenin