Reduction of cysteine-S -protecting groups by triisopropylsilane

Understanding acid lability of cysteine protecting groups.

Cys-disulfide bonds contribute to the stabilization of peptide and protein structures. The synthesis of these molecules requires a proper protection of Cys residues, which is crucial to prevent side-reactions and also to achieve the correct Cys connectivity. Here we undertook a mechanistic study of a set of well-known acid-labile Cys protecting groups, as well other new promising groups, in ord...

Synthesis and characterization of thiochromone S,S-dioxides as new photolabile protecting groups.

3-Arylthiochromone derivatives were synthesized as new photolabile protecting groups, in which the photoreactivity was switchable based on oxidation of the sulfur atom (sulfide and sulfone); the protected substrates , released the corresponding alcohols, amines or carbonxylic acids almost quantitatively under UV-light in neutral condition and the photoproduct showed high fluorescence intensity.

Amino acid-protecting groups.

Albert Isidro-Llobet, Mercedes Álvarez, Fernando Albericio Institute for Research in Biomedicine, Barcelona Science Park, Baldiri Reixac 10, 08028Barcelona, Spain. CIBER-BBN, Networking Centre on Bioengineering, Biomaterials and Nanomedicine, Barcelona Science Park, Baldiri Reixac 10, 08028-Barcelona, Spain. Laboratory of Organic Chemistry, Faculty of Pharmacy, University of Barcelona, 08028Bar...

Photolabile protecting groups and linkers

Wavelength-controlled orthogonal photolysis of protecting groups.

The selective control of a chemical process by the use of an electromagnetic wave has been a challenging goal for several decades. In this article, we describe for the first time the use of a monochromatic light beam to differentiate two different reactive centers. A direct application of this concept is found in the chemistry of protecting groups. Two different photolabile protecting groups we...