A Localized Enantioselective Catalytic Site on Short DNA Sequences and Their Amphiphiles.
JACS Au
; 2(2): 483-491, 2022 Feb 28.
Article
en En
| MEDLINE
| ID: mdl-35252997
ABSTRACT
A DNA-based artificial metalloenzyme (ArM) consisting of a copper(II) complex of 4,4'-dimethyl-2,2'-bipyridine (dmbipy-Cu) bound to double-stranded DNA (dsDNA) as short as 8 base pairs with only 2 contiguous central pairs (G for guanine and C for cytosine) catalyzes the highly enantioselective Diels-Alder reaction, Michael addition, and Friedel-Crafts alkylation in water. Molecular simulations indicate that these minimal sequences provide a single site where dmbipy-Cu is groove-bound and able to function as an enantioselective catalyst. Enantioselective preference inverts when d-DNA is replaced with l-DNA. When the DNA is conjugated to a hydrophobic tail, the obtained ArMs exhibit enantioselective performance in a methanol-water mixture superior to that of non-amphiphilic dsDNA, and dsDNA-amphiphiles with more complex Gâ¢C-rich sequences.
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1
Colección:
01-internacional
Base de datos:
MEDLINE
Idioma:
En
Revista:
JACS Au
Año:
2022
Tipo del documento:
Article
País de afiliación:
Estados Unidos