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Titolo:
REACTIONS OF MUCONALDEHYDE ISOMERS WITH NUCLEOPHILES INCLUDING TRI-O-ACETYLGUANOSINE - FORMATION OF 1,2-DISUBSTITUTED PYRROLES FROM REACTIONS OF THE (Z,Z)-ISOMER WITH PRIMARY AMINES
Autore:
BLEASDALE C; GOLDING BT; KENNEDY G; MACGREGOR JO; WATSON WP;
Indirizzi:
UNIV NEWCASTLE UPON TYNE,DEPT CHEM,BEDSON BLDG NEWCASTLE TYNE NE1 7RUTYNE & WEAR ENGLAND UNIV NEWCASTLE UPON TYNE,DEPT CHEM,BEDSON BLDG NEWCASTLE TYNE NE1 7RUTYNE & WEAR ENGLAND SHELL RES LTD,SITTINGBOURNE RES CTR SITTINGBOURNE ME9 8AG KENT ENGLAND
Titolo Testata:
Chemical research in toxicology
fascicolo: 4, volume: 6, anno: 1993,
pagine: 407 - 412
SICI:
0893-228X(1993)6:4<407:ROMIWN>2.0.ZU;2-J
Fonte:
ISI
Lingua:
ENG
Soggetto:
TRANS,TRANS-MUCONIC ACID; TRANS-MUCONALDEHYDE; BENZENE; ADDUCTS; METABOLITE; BACTERIAL; EXPOSURE; TOXICITY; PRODUCTS; LIVER;
Tipo documento:
Note
Natura:
Periodico
Settore Disciplinare:
Science Citation Index Expanded
Science Citation Index Expanded
Citazioni:
29
Recensione:
Indirizzi per estratti:
Citazione:
C. Bleasdale et al., "REACTIONS OF MUCONALDEHYDE ISOMERS WITH NUCLEOPHILES INCLUDING TRI-O-ACETYLGUANOSINE - FORMATION OF 1,2-DISUBSTITUTED PYRROLES FROM REACTIONS OF THE (Z,Z)-ISOMER WITH PRIMARY AMINES", Chemical research in toxicology, 6(4), 1993, pp. 407-412

Abstract

(Z,Z)-Muconaldehyde reacts with primary amines, including valine and lysine (epsilon-amino), to afford N-substituted-2-(oxoethyl)pyrroles, which were reduced with sodium borohydride to the more stable N-substituted-2-(hydroxyethyl)pyrroles. The formation of the pyrrole aldehydeswas performed in a variety of solvents including aqueous methanol. With tri-O-acetylguanosine, the putative pyrrole aldehyde derived from reaction at NH2 condenses with N-1 (guanine component) to afford a bicyclic adduct: pyr-rolo[1',2':3,4]pyrimido[1,2-a]purin-7(10H)-one (5a). This was hydrolyzed to olo[1',2':3,4]pyrimido[1,2-a]purin-7(10H)-one(5b). The structures of 5a and 5b were primarily based on NMR evidence and comparison with rrolo[1',2':3,4]pyrimido[2,1-b]pyrimidin-7-one(7), obtained from reacting (Z,Z)-muconaldehyde with 2-amino-4-hydroxy-6-methylpyrimidine. (E,Z)-Muconaldehyde also reacted with primary amines to give N-substituted-2-(oxoethyl)pyrroles, whereas (E,E)-muconaldehydegave bis-imines. The results described are discussed in the context of the carcinogenicity of benzene.

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Documento generato il 24/09/20 alle ore 10:53:31