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Titolo:
Oligonucleosides with a nucleobase-including backbone Part 3 - Synthesis of acetyleno-linked adenosine dimers
Autore:
Gunji, H; Vasella, A;
Indirizzi:
ETH Zurich, Organ Chem Lab, CH-8092 Zurich, Switzerland ETH Zurich Zurich Switzerland CH-8092 m Lab, CH-8092 Zurich, Switzerland
Titolo Testata:
HELVETICA CHIMICA ACTA
fascicolo: 11, volume: 83, anno: 2000,
pagine: 2975 - 2992
SICI:
0018-019X(2000)83:11<2975:OWANBP>2.0.ZU;2-P
Fonte:
ISI
Lingua:
ENG
Soggetto:
OLIGOSACCHARIDE ANALOGS; CYCLODEXTRIN ANALOGS; HYDROGEN-BOND; POLYSACCHARIDES; NUCLEOSIDES; NMR; MONOSACCHARIDES; SPECTROSCOPY; NUCLEOTIDES; LITHIATION;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Life Sciences
Physical, Chemical & Earth Sciences
Citazioni:
33
Recensione:
Indirizzi per estratti:
Indirizzo: Vasella, A ETH Zurich, Organ Chem Lab, Univ Str 16, CH-8092 Zurich, Switzerland ETH Zurich Univ Str 16 Zurich Switzerland CH-8092 Switzerland
Citazione:
H. Gunji e A. Vasella, "Oligonucleosides with a nucleobase-including backbone Part 3 - Synthesis of acetyleno-linked adenosine dimers", HELV CHIM A, 83(11), 2000, pp. 2975-2992

Abstract

The adenosine-derived dimers 14a-d and 15b-d have been prepared by coupling the protected 8-iodoadenosines 3 and 13 with the C(5')-ethynylated adenosine derivatives 5, 6, 11, and 12 (Scheme 4). Similarly, the 5'-epimeric dimer 16 was prepared by coupling 3 with the alkyne 8 (Scheme 5). The propargylic alcohol 4 was transformed into the N-benzoylated alkyne 5 and into the amine 6, while the epimeric alcohol 7 was converted to the epimeric amine 8and the 5'-deoxy analogues 11 and 12 (Scheme 3). Cross-coupling of the iodoadenosine 13 with the alkyne 5 to 14a was optimised;it is influenced by the N-benzoyl and the Et3SiO group of the alkyne, but hardly by the N-benzoylgroup of the 8-iodoadenosine. The alkyne is most reactive when it is O-silylated, but not N-benzoylated. Cross-coupling of the 5'-deoxyalkynes proceeded more slowly. The dimers 14a-d, 15b-d, and 16 were obtained in good yields (Table 2). Deprotection of 14d and 16 led to 18 and 20, respectively (Scheme 5). The diols 17 and 19 and the hexols 18 and 20 prefer the syn-conformation in (D-6)DMSO, completely for unit II and greater than or equal to 80% for unit I; they exhibit partially persistent intramolecular O(5')-H . . . N(3) H-bonds. The persistence increases from 18% (unit I of 19), 32% (unitII of 17 and 19), 45% (unit I of 17), 52% (unit II of 18 and 20), and 55% (unit I of 20) to 82% (unit I of 18).

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 29/11/20 alle ore 10:35:16