Practical synthesis of a dithiane-protected 3',5'-dialkoxybenzoin photolabile safety-catch linker for solid-phase organic synthesis.
The solution-phase preparation of the 3',5'-dialkoxybenzoin photolabile safety-catch linker 16 is described. Pivotal to this convenient synthesis is the selection of appropriate orthogonal protecting groups for the alkoxy functionalities present. The new linker can be readily loaded onto any standard amine-terminating resin under peptide-coupling conditions, without the need to protect the secondary alcohol functionality, and subsequently loaded with substrate. Alternatively, the loading efficiency of sterically hindered substrates can be enhanced by preloading the semiprotected linker variant 10 in solution prior to immobilization onto the resin. This second generation of benzoin photolabile safety-catch linkers provides greater control of both linker loading and resin attachment and should prove to be a more versatile and convenient form of the linker.
Cano
Montserrat
M
University Chemical Laboratory, University of Cambridge, Lensfield Road, Cambridge, CB2 1EW, UK.
Ladlow
Mark
M
Balasubramanian
Shankar
S
D001573:Benzoin / Q000138:chemical synthesis* / Q000737:chemistry / Q000528:radiation effects; D020650:Combinatorial Chemistry Techniques / Q000379:methods; D003432:Cross-Linking Reagents / Q000138:chemical synthesis* / Q000737:chemistry / Q000528:radiation effects; D010782:Photolysis; D012117:Resins, Synthetic / Q000737:chemistry / Q000528:radiation effects
D003432:Cross-Linking Reagents; D012117:Resins, Synthetic; D001573:Benzoin