Synthesis of pyrrole-imidazole-duocarmycin polyamide and its sequence selective DNA alkylation.
The new solid phase synthesis of sequence-specific DNA alkylating polyamides containing segment A of Du86 (Duo), N-methylimidazole (Im) and N-methylpyrrole (Py) amino acids is described. New monomer building block N-carboxylmethyl Py (Pyc) was synthesized from 2-methylpyrrolecarboxylate by eight steps. After normal coupling of FMOC-protected-Im and -Py monomer, the deprotection of silyl group generates free carboxylic acid. Introduction of various types of functional groups on solid support will be presented.
Fujiwara
T
T
Institute for Medical and Dental Engineering, Tokyo Medical and Dental University, Japan.
Tao
Z F
ZF
Saito
I
I
Sugiyama
H
H
D000478:Alkylation; D004247:DNA / Q000737:chemistry*; D019281:Dimerization; D004214:Distamycins / Q000737:chemistry; D007093:Imidazoles / Q000138:chemical synthesis* / Q000737:chemistry; D007202:Indicators and Reagents; D015394:Molecular Structure; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry
D004214:Distamycins; D007093:Imidazoles; D007202:Indicators and Reagents; D011758:Pyrroles; C030000:stallimycin; D004247:DNA