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Titolo:
N-15-multilabeled adenine and guanine nucleosides. Syntheses of [1,3,NH2-N-15(3)]- and [2-C-13-1,3,NH2-N-15(3)]-labeled adenosine, guanosine, 2 '-deoxyadenosine, and 2 '-deoxyguanosine
Autore:
Abad, JL; Gaffney, BL; Jones, RA;
Indirizzi:
Rutgers State Univ, Dept Chem, Piscataway, NJ 08854 USA Rutgers State Univ Piscataway NJ USA 08854 Chem, Piscataway, NJ 08854 USA
Titolo Testata:
JOURNAL OF ORGANIC CHEMISTRY
fascicolo: 18, volume: 64, anno: 1999,
pagine: 6575 - 6582
SICI:
0022-3263(19990903)64:18<6575:NAAGNS>2.0.ZU;2-G
Fonte:
ISI
Lingua:
ENG
Soggetto:
NITROGEN-15-LABELED OLIGODEOXYNUCLEOTIDES; N-15 NMR; BASE-PAIR; MASS-SPECTROMETRY; CHEMICAL-SHIFT; DEOXYNUCLEOSIDES; DNA; DEOXYADENOSINE; C-13; N1;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Life Sciences
Physical, Chemical & Earth Sciences
Citazioni:
23
Recensione:
Indirizzi per estratti:
Indirizzo: Jones, RA Rutgers State Univ, Dept Chem, POB 939, Piscataway, NJ 08854 USARutgers State Univ POB 939 Piscataway NJ USA 08854 NJ 08854 USA
Citazione:
J.L. Abad et al., "N-15-multilabeled adenine and guanine nucleosides. Syntheses of [1,3,NH2-N-15(3)]- and [2-C-13-1,3,NH2-N-15(3)]-labeled adenosine, guanosine, 2 '-deoxyadenosine, and 2 '-deoxyguanosine", J ORG CHEM, 64(18), 1999, pp. 6575-6582

Abstract

We report a high-yield route to the following specifically N-15- and C-13-multilabeled nucleosides:[1,3,NH2-N-15(3)]- and [2-C-13-1,3,NH2-N-15(3)]-adenosine; [1,3,NH2-N-15(3)]- and [2-C-13-1,3,-NH2-N-15(3)]-2'-deoxyguanosine. [1,3,NH2-N-15(3)]- and [2-C-13-1,3,NH2-N-15(3)]-2'-deoxyadenosine; [1,3,NH2-N-15(3)]- and [2-C-13-1,3,-NH2-N-15(3)]-2'-deoxyguanosine. In each set, the (13)C2 atom functions as a "tag" that allows the (15)N1 and (15)N3 atoms to be unambiguously differentiated from the untagged versions in N-15 NMRof RNA or DNA fragments. The key intermediate of this synthetic strategy for both the adenine and guanine nucleosides is [NH2, CONH2-N-15(2)]-5-amino-4-imidazolecarboxamide. The [2-C-13]-label is added through a ring closureusing [C-13]-sodium ethyl xanthate ((NaSCSOEt)-C-13). Enzymatic transglycosylation of either multilabeled 6-chloropurine or multilabeled 2-mercaptohypoxanthine and a final reaction with (NH3)-N-15 give the adenine and guanine nucleosides. This is the first report of a [3-N-15]-labeled guanine nucleoside.

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Documento generato il 11/07/20 alle ore 04:43:57