Synthesis of a hoechst 32258 analogue amino acid building block for directincorporation of a fluorescent, high-affinity DNA binding motif into peptides

Citation
C. Behrens et al., Synthesis of a hoechst 32258 analogue amino acid building block for directincorporation of a fluorescent, high-affinity DNA binding motif into peptides, BIOCONJ CHE, 12(6), 2001, pp. 1021-1027
Citations number
25
Language
INGLESE
art.tipo
Article
Categorie Soggetti
Chemistry & Analysis
Journal title
BIOCONJUGATE CHEMISTRY
ISSN journal
1043-1802 → ACNP
Volume
12
Issue
6
Year of publication
2001
Pages
1021 - 1027
Database
ISI
SICI code
1043-1802(200111/12)12:6<1021:SOAH3A>2.0.ZU;2-G
Abstract
The synthesis of a new versatile "Hoechst 33258-like" Boc-protected amino a cid building block for peptide synthesis is described. It is demonstrated t hat this new ligand is an effective mimic of Hoechst 33258 in terms of DNA affinity and sequence specificity. Furthermore, this minor groove binder wa s conjugated to a DNA condensing peptide (KSPKKAYK) by continuous solid-pha se peptide synthesis, and the conjugate exhibited increased DNA affinity (c a. 10-fold), but similar sequence preference compared to Hoechst 33258 as a nalyzed by DNaseI footprinting. Finally, the fluorescence quantum yield of the new chromophore is found to increase 30% upon binding to double strande d DNA.