Synthesis and photochemical behaviour of a T-T dimer containing an amide linkage.
A T-T dimer characterized by an amide linkage to replace the phosphodiester backbone has been synthesized using a modified radical strategy. The new synthetic approach makes use of a thymidin-3'-yl phosphorodithioate derivative as a precursor of 3'-allyl-3'-deoxythymidine. Standard chemical transformations of this derivative led to the desired T-T dimer incorporating an amide bond. The latter was irradiated with 254 nm wavelength light to yield mainly cyclobutane and [6-4] photoadducts.
Thomas
M
M
Institut de Chimie de Chimie des Substances Naturelles, CNRS 91198 Gif-sur-Yvette, France.
Clivio
P
P
Guillaume
D
D
Fourrey
J L
JL
D000577:Amides / Q000138:chemical synthesis / Q000737:chemistry*; D003503:Cyclobutanes / Q000737:chemistry; D010710:Phosphates / Q000737:chemistry; D010777:Photochemistry; D011740:Pyrimidine Dimers / Q000138:chemical synthesis / Q000737:chemistry*; D013936:Thymidine / Q000031:analogs & derivatives
D000577:Amides; D003503:Cyclobutanes; D010710:Phosphates; D011740:Pyrimidine Dimers; C083120:phosphorodithioic acid; D013936:Thymidine