We are presenting the synthesis of a phenylene ethynylene-based rod containing an Fmoc protected amino group and an activated acid which can be applied to peptide couplings. This linear amino acid analogue is applied to the synthesis of di-, tri- and pentamers. The pentamer has a molecular mass of 6.5 kDa and is characterized by (1)H NMR spectroscopy and MALDI-TOF MS. The method has potential f...

Peptide synthesis on cellulose using the SPOT technology follows the standard Fmoc-chemistry and can be performed manually or automated. This method allows the synthesis of low-cost peptide arrays containing around 900 large spots of addressable peptides on a cellulose sheet of 19 cm x 29 cm. These peptides can be cleaved from the cellulose support by ammonia gas and afterward spotted on glass ...

We report a light-sensitive histidine building block for Fmoc/tBu solid-phase peptide synthesis in which the imidazole side chain is coordinated to a ruthenium complex. We have applied this building block for the synthesis of caged-histidine peptides that can be readily deprotected by irradiation with visible light, and demonstrated the application of this approach for the photocontrol of the a...

The synthesis of enantiopure N-benzylidene nitrones of N-hydroxy-alpha-amino acids and their incorporation using standard Fmoc-based peptide chemistry into solid-supported peptide chains is described. Deprotection and resin cleavage affords N-terminal peptide hydroxylamines, which are the key substrates for chemoselective ligations with C-terminal peptide alpha-ketoacids. This general route is ...

Photochromic pyrans for applications in material and life sciences were synthesized via palladium-mediated cyanation, carbonylation and Sonogashira cross-coupling starting from bromo-substituted naphthopyran 1 and benzopyrans 2a/b. A novel photoswitchable benzopyran-based omega-amino acid 6 for Fmoc-based solid-phase peptide synthesis is presented. The photochromic behaviour of the 3-cyano-subs...

We present here a new, general, solid phase strategy for the synthesis of sequence independent peptidyl-fluoromethyl ketones using standard Fmoc peptide chemistry. Our method is based on the synthesis of bifunctional linkers which allows the incorporation of amino acid fluoromethyl ketone unit at the C-terminal end of peptide sequences. Application of this approach for the synthesis of activity...

A series of monoprotected aliphatic diamines (21 examples) were synthesized via continuous flow methods. The carbamates and enamines were obtained in 45-91% yields using a 0.5 mm diameter PTFE tubular flow reactor. Using readily accessible protecting group precursors, the procedure serves as an attractive alternative to existing batch-mode synthetic routes by providing direct, multigram access ...