Synthesis and /sup 1/H NMR spectroscopic characterization of trans-(Pt(NH/sub 3/)/sub 2//d(ApGpGpCpCpT)-N7-A(1),N7-G(3)/)
The reaction of trans-(Pt(NH/sub 3/)/sub 2/Cl/sub 2/) with the sodium salt of (d(ApGpGpCpCpT))/sub 2/ in aqueous solution at 37/sup 0/C was monitored by reversed-phase high-performance liquid chromatography and UV spectroscopy. Two intermediates, most likely monofunctional adducts, were observed, which subsequently formed one predominant single-stranded product, as well as several polymeric species proposed to be interstrand cross-linked products. The single-stranded adduct was structurally characterized by /sup 1/H NMR spectroscopy. From the pH dependence of the chemical shifts, two-dimensional homonuclear chemical shift correlation (COSY) spectroscopy, and one- and two-dimensional nuclear Overhauser effect (NOESY) experiments, the platinum(II) moiety was found to be coordinated to the N7 positions of adenine(1) and guanine(3), with the intervening guanine(2) base destacked from its neighboring residues. This intrastrand 1,3 adduct induces changes in the backbone torsion angles and caused the deoxyribose ring of adenine(1) to switch from a C2'-endo to a predominantly C3'-endo conformation. The other deoxyribose rings retain B DNA type conformations. The structure of trans-(Pt(NH/sub 3/)/sub 2//d(ApGpGpCpCpT)-N7-A(1),N7-G(3)/) differs from those previously reported for cis-DDP 1,2- and 1,3-intrastrand oligonucleotide adducts but is consistent with the structures of trans-DDP 1,3-intrastrand adducts of two previously reported trinucleotides.
- Research Organization:
- Massachusetts Institute of Technology, Cambridge
- OSTI ID:
- 5878256
- Journal Information:
- Biochemistry; (United States), Journal Name: Biochemistry; (United States) Vol. 26:18; ISSN BICHA
- Country of Publication:
- United States
- Language:
- English
Similar Records
Identification and characterization of a novel linkage isomerization in the reaction of trans-diamminedichloroplatinum(II) with 5 prime -d(TCTACGCGTTCT)
Monoclonal antibodies to DNA modified with cis- or trans-diamminedichloroplatinum(II)
Related Subjects
62 RADIOLOGY AND NUCLEAR MEDICINE
ABSORPTION SPECTROSCOPY
ADDUCTS
BARYONS
BIOSYNTHESIS
CHEMICAL SHIFT
CHROMATOGRAPHY
DNA ADDUCTS
ELEMENTARY PARTICLES
FERMIONS
HADRONS
LIQUID COLUMN CHROMATOGRAPHY
MAGNETIC RESONANCE
NUCLEAR MAGNETIC RESONANCE
NUCLEIC ACIDS
NUCLEONS
OLIGONUCLEOTIDES
ORGANIC COMPOUNDS
PH VALUE
PLATINUM COMPOUNDS
PROTONS
RESONANCE
SEPARATION PROCESSES
SPECTRA
SPECTROSCOPY
SYNTHESIS
TRANSITION ELEMENT COMPOUNDS
ULTRAVIOLET SPECTRA