Synthesis of a major mitomycin C DNA adduct via a triaminomitosene.
We report here the synthesis of two amino precursors for the production of mitomycin C and 10-decarbamoylmitomycin C DNA adducts with opposite stereochemistry at C-1. The triamino mitosene precursors were synthesized in 5 steps from mitomycin C. In addition synthesis of the major mitomycin C-DNA adduct has been accomplished via coupling of a triaminomitosene with 2-fluoro-O(6)-(2-p-nitrophenylethyl)deoxyinosine followed by deprotection at the N(2) and O(6) positions.
John Jay College of Criminal Justice, 524 West 59 Street, New York, NY 10019, USA. echampeil@jjay.cuny.edu
Elise
E
Champeil
Manuel M
MM
Paz
Elaan
E
Lukasiewicz
Wan S
WS
Kong
Stephanie
S
Watson
Anne-Marie
AM
Sapse
D018736:DNA Adducts / Q000138:chemical synthesis / Q000737:chemistry*; D007536:Isomerism; D016685:Mitomycin / Q000138:chemical synthesis / Q000737:chemistry*; D008937:Mitomycins / Q000737:chemistry*; D013816:Thermodynamics
D018736:DNA Adducts; D008937:Mitomycins; C056417:mitomycin C-DNA adduct; C067795:10-decarbamoylmitomycin C; C046001:mitosene; D016685:Mitomycin