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Titolo:
SYNTHESIS AND EVALUATION OF THE FULLY FUNCTIONALIZED BLEOMYCIN A(2) METAL-BINDING DOMAIN-CONTAINING THE MOYL-ALPHA-D-MANNOPYRANOSYL)-ALPHA-L-GULOPYRANOSYL DISACCHARIDE
Autore:
BOGER DL; TERAMOTO S; HONDA T; ZHOU JC;
Indirizzi:
SCRIPPS CLIN & RES INST,DEPT CHEM,10666 N TORREY PINES RD LA JOLLA CA92037
Titolo Testata:
Journal of the American Chemical Society
fascicolo: 28, volume: 117, anno: 1995,
pagine: 7338 - 7343
SICI:
0002-7863(1995)117:28<7338:SAEOTF>2.0.ZU;2-A
Fonte:
ISI
Lingua:
ENG
Soggetto:
DNA STRAND SCISSION; MAN-DESIGNED BLEOMYCINS; CARBON-MONOXIDE COMPLEX; SEQUENCE SPECIFICITY; ACTIVATED BLEOMYCIN; CLEAVING PROPERTIES; MAGNETIC-RESONANCE; ACTION MECHANISM; IRON COMPLEXES; FE-BLEOMYCIN;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Science Citation Index Expanded
Citazioni:
86
Recensione:
Indirizzi per estratti:
Citazione:
D.L. Boger et al., "SYNTHESIS AND EVALUATION OF THE FULLY FUNCTIONALIZED BLEOMYCIN A(2) METAL-BINDING DOMAIN-CONTAINING THE MOYL-ALPHA-D-MANNOPYRANOSYL)-ALPHA-L-GULOPYRANOSYL DISACCHARIDE", Journal of the American Chemical Society, 117(28), 1995, pp. 7338-7343

Abstract

The synthesis of the full metal binding domain of bleomycin A(2) complete with linkage to the moyl-alpha-D-mannopyranosyl)-alpha-L-gulopyranosyl disaccharide is detailed. Metal complexes (Fe(II), Fe(III)) of this full metal binding domain which includes the putative carbamoyl ligand residing in the disaccharide were found to cleave DNA in the presence of O-2 (Fe(II)) or H2O2 (Fe(III)) well above background cleavage and only 8-10x less efficiently than deglycobleomycin A(2) or 30-40x less efficiently than bleomycin A(2) and to do so in a nonsequence-specific manner with significantly reduced ratios of double versus single strand DNA cleavage (1:48 versus 1:6 for bleomycin A(2)). Thus, although the metal binding domain of bleomycin A(2) may play a role in determining the selectivity observed in DNA cleavage when incorporated intothe full natural product structure, the metal binding domain alone orin the presence of noncovalently linked tri- and tetrapeptide S failed to exhibit the sequence-selective DNA cleavage characteristic of bleomycin A(2).

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 23/09/20 alle ore 16:08:01