A Photolabile Carboxyl Protecting Group for Solid Phase Peptide Synthesis

Novel photolabile protecting group for carbonyl compounds.

[reaction: see text] A novel type of photo-protecting group for carbonyl compounds is described. The protecting group is readily accessed in one step from commercially available material. Installation of the protecting group upon the carbonyl compounds is achieved in excellent yields. The carbonyl compounds in their protected form are remarkably stable under various conditions and can be releas...

Two Useful Photolabile Surfaces for Solid-Phase Synthesis.

o-Nitrobenzyl-based photolabile surfaces 3 and 4 have been synthesized from 2-phenylcyclohexanone and aminopropylsiloxane-grafted controlled pore glass. The procedures are simple and inexpensive and generate materials whose minimally functionalized reactive chromophore should tolerate a range of subsequent chemistries. Time- and solvent-dependent analysis of photodegradation demonstrates a perf...

New safety-catch photolabile protecting group.

Photolabile protecting groups have proven their usefulness on many occasions. Their versions as linkers are however less attractive, as robustness and real orthogonality become critical issues. Safety-catch systems, where a preliminary activation phase is necessary, circumvent the problem of premature cleavage. In this work, we introduce a new safety-catch photolabile protecting group, whose cl...

Bichromophoric fluorescent photolabile protecting group for alcohols and carboxylic acids.

Novel bichromophoric fluorescent photolabile protecting group, (5-dansyloxy-3-hydroxynaphthalen-2-yl)methyl (DNS-NQMP), allows for the independent photochemical release and fluorescent imaging of caged substrates. Irradiation of DNS-NQMP-caged alcohols and carboxylic acids with 300 or 350 nm light results in fast (k(release) ~ 10(5) s(-1)), efficient (Φ = 0.2), and quantitative release of the s...

Solvents for solid-phase peptide synthesis.