Phenacyl ester derivatives bearing heterocycles as models for photocleavable linkers: synthesis and photolysis studies

• Published in: Tetrahedron Vol. 68; no. 38; pp. 8024 - 8032
• Main Authors: Fonseca, Andrea S.C., Gonçalves, M. Sameiro T., Costa, Susana P.G.
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 23.09.2012; Elsevier
• Subjects: Buffer solutions; Chemistry; Chemistry, Organic; Coumarin; Derivatives; Esters; Exact sciences and technology; General and physical chemistry; Heterocyclic compounds; Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms; Methyl alcohol; Noncondensed benzenic compounds; Organic chemistry; Peptides; Phenacyl derivatives; Photochemical; Photochemistry; Photocleavable linkers; Photolysis; Physical chemistry of induced reactions (with radiations, particles and ultrasonics); Physical Sciences; Preparations and properties; Quinolone; Science & Technology; Synthesis; Wavelengths; Phenacyl derivatives; Photocleavable linkers; Quinolone; Photolysis; Coumarin; ACIDS; PROTECTING GROUPS; CLEAVAGE; Peptides; Nitrogen heterocycle; Coumarine derivatives; Photochemical reaction; Oxygen heterocycle; Ester; Bromine Organic compounds; Reactor; Chemical synthesis; Quinolone derivatives; Oxygen nitrogen heterocycle; Methanol; Quinoline derivatives; Lactone; Organic bromine compounds; Buffer system; Wavelength; Irradiation; Peptide synthesis; Solid phase
• ISSN: 0040-4020; 1464-5416
• DOI: 10.1016/j.tet.2012.06.100

The synthesis of several phenacyl ester derivatives linked to oxygen and nitrogen heterocycles, benzoquinolone and (benzo)coumarins, was carried out in an effort to obtain systems that could be applied as photocleavable (bi)functional linkers for solid phase peptide synthesis. The heterocycles were attached to a spacer, with different lengths, followed by coupling to 2-bromo-1-phenylpropan-1-one, acting as a model for the solid support. Photolysis studies of the resulting phenacyl ester derivatives were carried out by irradiation in a photochemical reactor at different wavelengths (300, 350 and 419nm), in methanol/HEPES buffer solution (80:20). [Display omitted]