Quantum molecular modeling of the interaction between guanine and alkylating agents--2--nitrogen mustard.
The alkylation mechanism of guanine by nitrogen mustard (HN2) was studied by using a supermolecular modeling at the ab initio 6-31G level. Our computations show that interaction of guanine with the aziridinium form of HN2 necessitates a transition state for the N7 alkylation route. The pathway of N7-guanine alkylation by nitrogen and sulfur mustards is discussed on the basis of the Molecular Electrostatic Potential and HOMO-LUMO properties of these molecules.
Hamza
A
A
Laboratory of Biophysics, University of Nice-Sophia Antipolis, France.
Broch
H
H
Vasilescu
D
D
D000477:Alkylating Agents / Q000737:chemistry*; D000478:Alkylation; D001388:Aziridines / Q000737:chemistry; D006147:Guanine / Q000737:chemistry* / Q000378:metabolism; D008466:Mechlorethamine / Q000737:chemistry*; D008956:Models, Chemical; D008958:Models, Molecular; D011789:Quantum Theory
D000477:Alkylating Agents; D001388:Aziridines; D008466:Mechlorethamine; C033132:aziridine; D006147:Guanine