Synthetic replacement of the methylamino group of neocarzinostatin chromophore with hydroxyl prohibits thiol activation in organic solvents and diminishes the rate and efficiency of thiol-promoted DNA cleavage in water

Authors
Myers, AG Liang, J Hammond, M
Citation
Ag. Myers et al., Synthetic replacement of the methylamino group of neocarzinostatin chromophore with hydroxyl prohibits thiol activation in organic solvents and diminishes the rate and efficiency of thiol-promoted DNA cleavage in water, TETRAHEDR L, 40(28), 1999, pp. 5129-5133
Citations number
26
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
28
Year of publication
1999
Pages
5129 - 5133
Database
ISI
SICI code
0040-4039(19990709)40:28<5129:SROTMG>2.0.ZU;2-2
Abstract
A synthesis of the neocarzinostatin chromophore analog 2, in which the 2'-N -methylamino group of the natural product has been replaced by a hydroxyl g roup, is described. Thiol addition experiments in organic solvents and DNA- cleavage studies in aqueous solution are also described, and provide furthe r support for the proposed participation of the carbohydrate methylamino gr oup in neocarzinostatin activation. (C) 1999 Elsevier Science Ltd. All righ ts reserved.