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2006

Faculty of Science - Papers (Archive)

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Full-Text Articles in Physical Sciences and Mathematics

Polyamide Platinum Anti-Cancer Complexes Designed To Target Specific Dna Sequences, David Jaramillo, Nial J. Wheate, Stephen F. Ralph, Warren A. Howard, Yitzhak Tor, Janice Aldrich-Wright Jan 2006

Polyamide Platinum Anti-Cancer Complexes Designed To Target Specific Dna Sequences, David Jaramillo, Nial J. Wheate, Stephen F. Ralph, Warren A. Howard, Yitzhak Tor, Janice Aldrich-Wright

Faculty of Science - Papers (Archive)

Two new platinum complexes, trans-chlorodiammine[N-(2-aminoethyl)-4-[4-(N-methylimidazole-2-carboxamido)-N-methylpyrrole-2-carboxamido]-N-methylpyrrole-2-carboxamide]platinum(II) chloride (DJ1953-2) and trans-chlorodiammine[N-(6-aminohexyl)-4-[4-(N-methylimidazole-2-carboxamido)-N-methylpyrrole-2-carboxamido]-N-methylpyrrole-2-carboxamide]platinum(II) chloride (DJ1953-6) have been synthesized as proof-of-concept molecules in the design of agents that can specifically target genes in DNA. Coordinate covalent binding to DNA was demonstrated with electrospray ionization mass spectrometry. Using circular dichroism, these complexes were found to show greater DNA binding affinity to the target sequence:  d(CATTGTCAGAC)2, than toward either d(GTCTGTCAATG)2, which contains different flanking sequences, or d(CATTGAGAGAC)2, which contains a double base pair mismatch sequence. DJ1953-2 unwinds the DNA helix by around 13°, but neither metal complex significantly affects the DNA melting temperature. Unlike simple DNA minor …


Asymmetric Synthesis Of Anti-1,2-Amino Alcohols Via The Borono-Mannich Reaction: A Formal Synthesis Of (-)-Swainsonine, Christopher W. G. Au, Stephen G. Pyne Jan 2006

Asymmetric Synthesis Of Anti-1,2-Amino Alcohols Via The Borono-Mannich Reaction: A Formal Synthesis Of (-)-Swainsonine, Christopher W. G. Au, Stephen G. Pyne

Faculty of Science - Papers (Archive)

Chiral α-hydroxy-aldehydes generated in situ by the ADH reaction of vinyl sulfones undergo a borono-Mannich reaction with β-styrenyl boronic acid and primary amines to give anti-1,2-amino alcohols in high enantiomeric purities (ee 83-95%). This new method allows much more rapid access to these valuable chiral building blocks that has been used in a short formal synthesis (10 synthetic steps from 4-penten-1-ol) of (-)-swainsonine.