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2'-Hydrazine oligonucleotides: synthesis and efficient conjugation with aldehydes. 2005

Timofei S Zatsepin, and Dmitry A Stetsenko, and Michael J Gait, and Tatiana S Oretskaya
Department of Chemistry, M. V. Lomonossov Moscow State University, 1 Leninskie gory, Moscow 119992, Russia.

Oligodeoxyribonucleotides that contain a novel nucleoside, 2'-O-(2-hydrazinoethyl)uridine, were synthesized by sodium cyanoborohydride reduction of hydrazones formed from 2'-aldehyde oligonucleotides and FmocNHNH2 followed by ammonia deprotection. 2'-Hydrazine oligonucleotides were used successfully to obtain a series of conjugates with various aldehydes by hydrazone formation. The method was shown to be suitable for the preparation of oligonucleotide-peptide conjugates.

UI MeSH Term Description Entries
D009838 Oligodeoxyribonucleotides A group of deoxyribonucleotides (up to 12) in which the phosphate residues of each deoxyribonucleotide act as bridges in forming diester linkages between the deoxyribose moieties. Oligodeoxynucleotide,Oligodeoxyribonucleotide,Oligodeoxynucleotides
D006834 Hydrazines Substituted derivatives of hydrazine (formula H2N-NH2). Hydrazide
D000447 Aldehydes Organic compounds containing a carbonyl group in the form -CHO. Aldehyde
D014529 Uridine A ribonucleoside in which RIBOSE is linked to URACIL. Allo-Uridine,Allouridine,Allo Uridine
D019032 Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization A mass spectrometric technique that is used for the analysis of large biomolecules. Analyte molecules are embedded in an excess matrix of small organic molecules that show a high resonant absorption at the laser wavelength used. The matrix absorbs the laser energy, thus inducing a soft disintegration of the sample-matrix mixture into free (gas phase) matrix and analyte molecules and molecular ions. In general, only molecular ions of the analyte molecules are produced, and almost no fragmentation occurs. This makes the method well suited for molecular weight determinations and mixture analysis. Laser Desorption-Ionization Mass Spectrometry, Matrix-Assisted,MALD-MS,MALDI,Mass Spectrometry, Matrix-Assisted Laser Desorption-Ionization,Mass Spectroscopy, Matrix-Assisted Laser Desorption-Ionization,Matrix-Assisted Laser Desorption-Ionization Mass Spectrometry,Spectroscopy, Mass, Matrix-Assisted Laser Desorption-Ionization,MALDI-MS,MS-MALD,SELDI-TOF-MS,Surface Enhanced Laser Desorption Ionization Mass Spectrometry,Laser Desorption Ionization Mass Spectrometry, Matrix Assisted,MALDI MS,Mass Spectrometry, Matrix Assisted Laser Desorption Ionization,Mass Spectroscopy, Matrix Assisted Laser Desorption Ionization,Matrix Assisted Laser Desorption Ionization Mass Spectrometry

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