Isostere-based design of 8-azacoumarin-type photolabile protecting groups: a hydrophilicity-increasing strategy for coumarin-4-ylmethyls.
Described is the development of 8-azacoumarin-4-ylmethyl groups as aqueous photolabile protecting groups. A key feature of the strategy is the isosteric replacement of the C7-C8 enol double bond of the Bhc derivative with an amide bond, resulting in conversion of the chromophore from coumarin to 8-azacoumarin. This strategy makes dramatically enhanced water solubility and facile photocleavage possible.
Institute of Biomaterials and Bioengineering, Tokyo Medical and Dental University , Chiyoda-ku, Tokyo 101-0062, Japan.
Tetsuo
T
Narumi
Hikaru
H
Takano
Nami
N
Ohashi
Akinobu
A
Suzuki
Toshiaki
T
Furuta
Hirokazu
H
Tamamura
D000577:Amides / Q000737:chemistry; D001372:Aza Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D003374:Coumarins / Q000138:chemical synthesis* / Q000737:chemistry*; D057927:Hydrophobic and Hydrophilic Interactions; D015394:Molecular Structure; D010777:Photochemistry
D000577:Amides; D001372:Aza Compounds; D003374:Coumarins